UC-NRLF B M 33D ISb DEPOEIPTIYE CATALOGUE ESSE^iilL vlLS AND Organic Chemical Peepaeations f'Mrpx. EO BY FREDERICK B POWi^R, Ph.G., Ph.D. Director- of the Labo ntories nf Frifzsche Brothers, at Garfield, X. J. PUBLISHED BY FEITZSCHE BEOTHERS NEW YORK AND Garfield, N. .T. Bkanch of SCHIMMEL & CO. LeIPSIC and r'fAOllE REESE LIBRARY OF 1HI-: UNIVERSITY OF CALIFORNIA. l^eceived , iqo . z/lccessioi! No. J-^-tri^ • Cla^sNi). DESCRIPTIVE CATALOGUE OF Essential Oils Organic Chemical Preparations COMPir^ED BY FREDERICK B. POWER, Ph.G., Ph.D. Director of the Lahnratorics of Fritzstche Brothers, at Garfield, N, J. ra^ PUBLISHED BY FEITZSCHE BROTHERS NEAV YORK AND Garfield, N. .T. ( BRA^-CH OF SCHDIMEL & CO. Leipsic and Prague u '^^(. ^%=^^ ^#\?^ Entered, according to Act of Congress, in the year 1894, by Feitzsche Beothees, in the Office of the Librarian of Congress at Washington, D. C. CHEEOUNY PEINT, NEW TOBK PREFACE. rriHE title of the little work here presented is believed to correctly indicate its character and scope. It was not the design to pro- duce a treatise on essential oils in which all the points of interest con- nected therewith might be considered, such as the character and com- mercial soui-ces of the crude materials, and the methods of obtaining the oils therefrom, nor has any attempt been made to present detailed information regarding the chemical characters of the large number of individual substances of which the various essential oils are composed. The aim of this compilation was rather to bring together in a some- what clasfjified and convenient form all the essential oils and chemi- cal preparations which are now or have heretofore been produced in either our American or German laboratories, with a synopsis of their principal characters, such as botanical source, physical properties, chemical constituents or composition, tests for purity, etc. Although a few of the oils here enunaerated are not regularly manufactured by us, they represent in such cases either those which have been distilled for jmrely scientific or experimental purposes, and often for the first time, or those which, for commercial purposes, are produced almost exclusively in their native countries, such as the oils of the Citrus fruits, Cassia Oil, the Indian Grass Oils, and similar important articles, but which have been prepared in the laboratories of our Leipsic house on a smaller scale for the purpose of establish- ing the chemical and physical characters of perfectly pure products. Through the controlling inflvience of such investigations many foreign oils which were heretofore largely adulterated, even at the place of production, have been greatly improved in quality, and greater uni- formity attained. iii 92419 IV PREFACE. Wliile the essential oils produced in our American laboratories and in those of our Leipsic house are known to be absolutely jiure. and to rejireseut normal distillates from the best crude material, the investigations referred to have rendered it possible for us to adopt standards of purity for oils not distilled by ourselves, and thus to fur- nish these from the first sources of supplj', and also of the finest at- tainable quality. As an examjile of our endeavors in this dnection, we may refer to the investigation of Oil of Peppermint. It will be apparent that in the prejjaration of this little work the facts and information have been chiefly gathered from the series of "Berichte" or "Semi -Annual Reports" regularly issued by our Leipsic house (Messrs. Schimmel & Co.). These have been carefully reviewed for this purpose, and special aid has been afforded in the task by utilizing the table appended to the Bericht {Semi- Annual Report) for October, 1893. It may be observed, however, that the work has been so extended as to include a few oils not enume- rated in the table i-eferred to, that more detailed descrij^tions and tests are recorded, and a further classification adopted, which sepa- rates the oils recognized by the U. S. Pharmacopceia of 1890 from the non-official ones. A third subdivision of the work includes a list of Organic Chemical Preparations, a considerable number of which rep- resent the well characterized and more important constituents of the essential oils. In this synoptical treatment of the subject it was not considered expedient to include all the numerous citations of current literature relating thereto, nor was it deemed practicable to consider the large number of derivatives of individual substances, which, as those familiar with the subject are aware, would require a series of ex- tended monographs. Those desiring more complete information on many points will naturally refer to recent works on organic and pharmaceutical chemistry and the dictionaries of chemistry, while the more important original publications may be found in Liebig's Annalen der Chemie, in the Beridite der deittschen cliemisclien Gesell- schaft (Berlin), the Journal fur praktische Chemie (Leipzig), Comptes rendns (Paris), Bulletin de hi Societe chimiqite (Paris), Journal of the Chemical Society (London), American CJieniical Journal (Baltimore), and the leading pharmaceutical periodicals. When these sources of PREFACE. V inforniatiou are not available, abstracts of original papers may usually be found in the Jahveshericht der Chenite, JaluimcJi do- Clicmie (Braunschweig), Jahreshericht der Phannacie (by Dr. H. Beckurts), the British Yearbook of Pharviacy, and the Report on the Progress of Pharmacy in the Proceedings of the American Pharmacetdical Asso- ciation. It may be stated by way of explanation that, in order to avoid repetition, the specific gi-avities noted in the following pages refer to a temperature of 15° C, unless otherwise specified, and that the optical rotations refer uniformly to a tube of 100 millimeters. Tlie solubilities refer to parts by volume, and to alcohol of a specified strength by volume. In the arrangement of the official oils the descriptions are given under the official English titles, such as Oil of Hedeoriui for Oil of Pennyroyal, Oil of Myrcia for Oil of Bay, etc., and with the non- official oils the descriptions follow the names by which they are most commonly known. Where this for any reason has not seemed practicable, suitable cross-references are given, which, together with a strictly alphabetical arrangement, renders a further index i-eference unnecessar}^ In the preparation of this little work we have indulged the hope that it may be found useful for reference, and to possess in some degree both scientific and practical interest and value. With consideration of the intense activity now being manifested in the truly scientific study of the constituents of essential oils, it may also serve to indi- cate the deficiencies of existing knowledge in many directions, and thus incite to further careful research in this interesting and fruitful branch of science. FRITZSCHE BROTHERS. New York, June, 1894. i ^^M PART I. OFFICIAL ESSENTIAL OILS. Recognized by the PharmaeoiDceia of the United States of Anieriea. Seventh Decennial Revision, 1890. Oil of Allspice, see Oil of Pimeuta. Oil of American Wormseed, see Oil of Clieiiopoclinm. Oil of Anise. Olenni Anisi. (German: Anis-Oel.) Distilled from the fruit of Pimpbiella Amsuni Linne (Nat. Ord. Umhelliferce). ' ' A colorless or pale yellow liquid, having a characteristio, aromatic odor and taste. Specific gravity 0.980 to 0.990 at 17° C."* Its optical rotation is very slightly to the left. " At a temxjerature usually between 10° and 15° C. (14° to 19°, Schinnnel & Co.) it solidifies to a white, crystalline mass." The chief jwrtion of the oil, over 90 per cent., consists of anethol Cio Hio O (see the latter, under Chemical Preparations, Part III). The chemical character of the other constituent of the oil, which is liquid at ordinary temperatures, has not yet been determined, but it is apparently a terpene. Oil of Anise is used medicinally as an aromatic carminative and stimulant, and also for imparting flavor to liquors. Oil of Bay, see Oil of Myrcia. Oil of Bergamot. Oleum Bergamott*. (German: Bergamott-Oel.) Obtained by expression from the rind of the fresh fruit of Citrus Bergamia Risso et Poiteau (Nat. Ord. Butacece). " A greenish or greenish -yellow liquid, having a peculiar, very fragrant odor, and an aromatic, bitter taste. Specific gravity 0.880 to 0.885" (0.883 to 0.886, Schimniel & Co.). "Its optical rotation should not be more than 20 to the right in a 100 Mm. tube." The rotation of a pure oil usually varies from +9" to +15°. (See Schimmel & Co.'s Bericht, April, 1893, p. 19, and April, 1894, p. 21.) "It is * The quotutiou marks in the te.vt of the official essential oils antl chemi- cals denote the portions abstractetl from the text of the U. S. Pharmacopoeia. 8 OFFICIAL ESSENTIAL OILS. soluble at 20^ C. iu l.o to 2 volumes of alcohol of 80 per cent, by voliune. If about 2 granuues of the oil be evaporated in a cap- sule, on a water bath, until the odor has completely disappeared, a soft, green, homogeneous residue should be left, aTuounting to not more than about 6 per cent, of the oil (absence of fatty oils)." The oil contains linionene, dipentene, linalool and linaloyl acetate, the latter in amounts of about 36 to 39 per cent. The substance deposited from freshly expressed Oil of Bergamot is termed bergapten. It forms colorless, needle-shaped crystals, of the compositionCi.Hf Oj, or Cii H^02 Scliimmel & Co.). It deviates polarized light slightly to the left. The oil contains cineol, terpineol, and one or more terjjenes. The green color of the oil is usually due to ti'aces of copper. Oil of Cajuput is used medicinally, internally as a stimulant, dia- phoretic and vermifuge, and externally as a local stimulant and rubefacient. Oil of Caraway. Oleum Cari. (Gennaii : Kiiiiunol-Oel.) Distilled froni the fruit of Cariun Carvi Linne (Nat. Ord. Uinhclli- fercc). "A colorless or pale yellow, thin liquid, having the characteristic aromatic odor of caraway, and a mild, spicy taste. Specific gravity 0.910 to 0.920" (0.905 to 0.915, Scliimmel & Co.). Optical rotation -|-75° to -|-85°. It contains dextrogyrate limonene (formerly known as carvene) and dextrogyrate carvol, both of which are more fully de- scribed under Chemical Preparatioiih, Part III. Oil of Caraway is used medicinally as an aromatic stimulant and carminative, and also to impart llavor to licjuors and other mixtin-es. OFFICIAL ESSENTIAL OILS. 11 Oil of Cassia, see Oil of Ciiniaiiioii. Oil of Clieiiopotlium. Oleum Chenopodii. [Oil of American WonuswMi.] (German : Chcnopodivira-Oel.) Distilled from the fruit of Chenopodiiun ambrosioidc-s Linue, var. anthelminticum Gray (Nat. Ord. Clienopodiacea'). " A colorless or yellowish liquid, haviug a characteristic, penetrat- ing odor, and a pungent and bitterish taste. Specific gravity about 0.970." Tlie characters of this oil are subject to considerable variation, which appear to depend chiefly upon its age. Thus commercial oils from reliable sources we have found to have the specific gravity 0.970, optical rotation — 5° 35' to — 6° 20', and to form a clear solution with ten times their volume of 70 per cent, alcohol, while an oil distilled in our Garfield factory has, in its fresh state, a specific gravity of 0.910, an optical rotation of — 18° 55', and does not form a perfectly clear solution with ten times its volume of 70 per cent, alcohol. The oil is stated to consist of ahydrocarbon CioHui, and a body of the composition CioHif, O {Amer. Jonrn. Pharm., xxvi, p. 405), but is deserving of more thorough examination. Oil of Chenopodium is used chiefly as an anthelmintic. Oil of Clienopodium Leaves, which is not ofiicial, has also been distilled in our Garfield factory. It has a yellowish color and an odor strongly resembling the oil from the frviit. The freshly distilled oil has a specific gravity of 0.879, and an optical rotation of — 33° 55'. It is insoluble in 70 per cent, alcohol. Oil of Ciunamoii. Oleum Ciunamoml. [Oil of Cassia.] (German: Cassia-Oel.) Distilled from undetermined species of Cinnamomum (Nat. Ord. Laurinea'), grown in China. "A yellowish or brownish liquid, becoming darker and thicker by age and exposure to the air, liaviug the cliaracteristic odor of cinnamon, and a sweetish, spicy and burning taste. Specific gravity 1.055 to 1.065." It consists chiefly of cinnamic aldehyde Ch H; — COH, witli some cinnamyl acetate C^ Hu — C2 H3 O2. The official or commercial Oil of Cassia appears to be obtained chiefly from the leaves, or from the latter mixed with leaf stems and young twigs. (See Schimmel & Co. 's Bericht, October, 1893, p. 13.) It was formerly much adulterated with resin, j)etroleum, fatty oils, etc. , which may be detected by the tests given in the U. S. Pharmacopoeia. The best criterion of the value of tlie oil is the determination of the amount of cinnamic aldehyde, wliich should not be less than 75 per l-'i OFFICIAL ESSENTIAL OILS. ceut. This can he accomplished l:)y hriugiug 10 Cc. of the oil, lueasureil by a ]jiijette, iuto a glass flask having a capacity of about 100 Cc. , and provided with a narrow neck about 13 Cm. long and 8 Mm. inside dianieter, which is graduated in tenths of a cubic centimeter. A small amount of solution of sodium bisulphite, containing about 30 per cent, of the salt, is then added to the oil, and the mixture agitated, when a semi-solid mass will be formed. The flask is now placed in a bath of boiling water, and, when tha mixture is completely liquefied, a further amount of the bisulphite solution is added until the flask is about three-fourths full. The mixture is again heated in the water bath, with frequent agitation, until all the solid particles have become dissolved, and there is obtained a clear, oily liquid floating on the surface of the aqueous solution. Finally, so much bisulphite solution is added that the oily layer, which represents the non-aldehyde bodies, will rise completely m the upper part of the neck of the flask. After cooling, the volume of the non-aldehj'des is deducted from the 10 Cc. of oil originally used, and the remainder, when multiplied by 10, will indicate the pei'centage amount (by volume) of cinnamic aldehyde con- tained in the oil. Oil of Cinnamon is used chiefly for imparting its agreeable flavor to other mixtures, and for perfuming ordinary soaps, etc. In order to determine the character of the oils afforded by dif- ferent parts of the plant yielding Cassia Cinnamon, Messrs. Schimmel & Co. have distilled from authentic crude material the following products. (See Bericht, October, 1892, p. 13): Oil of Cassia Bark. Specific gravity l.n:}."). Contains 88.9 per cent, of cinnamic aldehyde. Oil of Cassia Buds. Specific gravity 1.026. Contains 80.4 per cent, of cinnamic aldehyde. Oil of Cassia Bud Stems. Specific gravity 1.040. Contains 92 per cent, of cinnamic alde- hj'de. Oil of Cassia Leaves (witli leaf stems and young twigs). Specific gravity LO")."). Contains 93 per cent, of cinnamic alde- hyde. The above figures represent the results of single distillations, and in a more extended series of observations some variations would doubtless be found. (See Berivht, April. 1894, p. 13.) OFFICIAL ESSENTIAL OILS. 13 The following non-official, but closely related cinnamon oils, may also conveniently be considered here; Oil of Cinnaiiioii, Ceylon. (German: Ceylon Zimmt-Ocl.) Distilled from the bark of Cinnamomuvi Zeylanicum Breyn (Nat. Ord. Laurinece). A pale yellow liquid, having the characteristic odor of cinnamon, and a sweetish, burning, and spicy taste. Specific gravity 1.025 to l.OB."). It consists chiefly of cinnamic aldehyde, with some eiigenol and phellandrene. The bark of Cinnamonmm Wiglitii Meissn., of Northern India, yields a highly aromatic oil, having a specific gravity of 1.01, and boiling between 130° and 170° C. Oil of Ciiuiamoii Leaves. (Gcrmati : Zimmtblatter-Oel.) Distilled from the leaves of Cinnamonmm Zeylanicum Breyn (Nat. Ord. Laurinece). A pale yellow, limpid liquid, having a combined cinnamon and clove-like odor. Specific gravity 1.044 to 1.060. It contains cinnamic aldehyde, eugenol, and safrol. Oil of Ciuuamoii Root. (German: Zimmtwurzel-Oel.) Distilled from the bark of the root of Cinnamonium Zeylanicum Breyn (Nat. Ord. Laurinece). A nearly colorless liquid, having a remarkably strong odor of common camphor, which partially separates from the oil at ordinary temperatures. Oil of Cloves. Oleum Caryopliylli. (German: Nelken-Oel.) Distilled from cloves, the unexpanded flowers of Eugenia aromatica (Linne) O. Kuntze (Nat. Ord. Myrtacece). "A pale yellow, thin liquid, becoming darker and thicker by age and exposure to the air, having a strongly aromatic odor of cloves, and a pungent and spicy taste. Specific gravity 1.060 to 1 067" (1.060 to 1.070, Schimmel & Co.l. It deviates polarized light slightly to the left. It boils between 250° and 260° C, the greater part distilling over between 250° and 251° C. "1 Cc. of the oU should form a clear solution with 2 Cc. of a mixture of 2 volumes of alcohol and 1 volume of water (absence of petroleum, most fatty oils, oil of turpentine, etc.)." The oil contains eugenol, about 80 to 90 per cent, (see the latter, under Chemical Preparations, Part III), and a sesquiterpene CisHaj, termed caiyophyllene, which boUs at about 255° C. (Liebig's Annalen, 271, p. 285). U OFFICIAL ESSENTIAL OILS. For tlie estimation of eugenol in the form of its benzoyl compound, see Pliann. Centralhalle, 1891, p. GS'J; also Amer. Journ. Pharin., 1893, p. 2G, and Schimmel & Co.s Berkht, April, 1892, p. 28. Oil of Cloves is a powerful aromatic, and also possesses antiseptic proijerties. It is used medicinally, both internallj' and externally, esjpecially to allay the pain of carious teeth, and also for imparting its peculiar flavor to other mixtures. Oil of Clove Steins has a specific gravity of 1.055 to 1.065. It may be distinguished by its odor, which is not so fine as that of true Oil of Cloves. Oil of Copaiba. Oleum Copaibii'. (German : Copaivabalsam-Oel.) Distilled from Copaiba, or the so-called Balsam of Copaiba, the oleoresin of Copaiba Langsdorffil (Desfontaines) O. Kuntze, and of other species of Copaiba (Nat. Ord. Leguminosie). ' ' A colorless or pale yellowish liquid, having the characteristic odor of copaiba, and an aromatic, bitterish and pungent taste. Specific gi-avity 0.890 to 0.910" (0.900 to 0.910, Schimmel & Co.). It deviates polarized light to the left; an oil distilled in our Gai"field factory showing an optical rotation of — 8° 6 . The oil consists chiefly of caryophyllene Ci5H-24. Oil of Copaiba is considered to have the same effects on the system as Copaiba. Oil of Coriander. Oleum Coriaudri. (German: Coriander-Oel.) Distilled from the fruit of Coriaitdruiii safivniii Linne (Nat. Ord. Umbellifeirc). "A colorless or slightly yellowish liquid, liuviug Uie characteristic, aromatic odor of coriander, and a warm, spicy taste. Specific gravity 0.870 to 0.885" (0.874 to 0.882, Schimmel & Co.). Optical rotation +4° to -[-13° " 1 Cc. of the oil should form a clear solution with 3 Cc. of a mixture of 3 volumes of alcohol and 1 volume of water." This test will serve to detect adulterations with oil of sweet orange peel, oil of tmpentine, etc. The oil contains linalool (formerly termed coriandroT) and pineue. Oil of Coriander is aromatic and carminative, and is often used to correct the odor and taste of other mixtures. Oil of Cubeb. Oleum Cubebte. (German : Cubebcn-Oel.) Distilled from the unripe fruit of Piper Cubeba Linne filius i Nat. Ord. Piperacece). OFFICIAL ESSENTIAL OILS. 15 " A colorless, pale greenish or yellowish liquid, having the char- acteristic odor of cubeb, and a warm, caniphoraceous, aromatic taste. Specific gravity about 0.920" (0.910 to 0.930, Schimmel & Co.). The oil consists chiefly of cadinene C15HJ4, with some dipentene, and, when old, or distilled from old fruit, contains cubeb camphor C15H24. Ho O. Oil of Cubeb possesses the aromatic proi)erty of the fruit, and when taken internally .produces symptoms similar to oil of copaiba. Oil of Erigerou. Oleum Erigerontis. [Oil of Fleabane.] (German: Erigeron-Oel.) Distilled from the fresh, flowering herb of Erigeron canade71.se Linne (Nat. Ord. Composite^). " A pale yellow, limpid liquid, becoming darker and thicker by age and exposure to the air, having a peculiar, aromatic, ]jersistent odor, and an aromatic, slightly pungent taste. Specific gravity about 0.850, increasing with age" (0.855 to 0.890, Schimmel & Co.). The larger jmrt of the oil distills between 175° and 180° C. It consists chiefly of dextrogyrate limonene, together with a substance wliich readily becomes decomposed or polymerized by the action of heat, and which can therefore not be distilled under ordinary pressure. (See Ber. d. deidsch. chem. Ges., 15, 1882, p. 2854 ; Amer. Journ. Pharm., 1883, p. 372 ; Liebig's Anualen, 227, p. 292 ; Pharm. Rundschau, 1887, p. 201 ; and Proc. Wis. Pharm. Assoc, 1893, p. 65.) Oil of Erigeron has been employed medicinally for controlling uterine hemorrhage, and is supposed to act very much like the oil of turpentine, although much less irritant and stinfulating. Oil of Eucalyptus. Oleum Eucalypti. (German : Eucalyptus-Ool.) Distilled from the fresh leaves of Eucalyptus globidus Labillardiere, Eucalyptus oleosa F. von Mueller, and some other species of Euca- lyptus (Nat. Ord. Myrtacece). " A coloi-less or faintly yellowish liquid, having a characteristic, aromatic, somewhat camphoraceous odor, and a pungent, spicy and cooling taste. Specific gravity 0.915 to 0.925. If 1 Cc. of the oil be mixed with 2 Cc. of glacial acetic acid, and 1 or 2 Cc. of a saturated, aqueous solution of sodium nitrite be gradually added, the mixture, when gently stirred, should n()t form a crj'stalline mass (distinction from oils of Eucalyptus containing a considerable proportion of phellandrenej." The test for phellandrene is rendered somewhat more delicate by the following method of procedure: 1 Cc. of the oil is mixed with 5 Cc. of petroleum benziu, 1 or 2 Cc. of a concentrated solution of sodium nitrite added, and subsequently glacial acetic acid ^^' OFFICIAL ESSENTIAL OILS. additi;n^ ''ifllZllZetl^''^^^^ ^f^^tion after each crvstaUine nitrite, Co H.eN,0^n ^°>' ^o^^iflerable amount its on of EucalUsM^^^^^^^^ "^'^^^^^ ^-- ^^- ^-in solution. andeontaLcined(euc^^^^^^^^ '-'-'^-- of ^1^ to ^2CP of valeric, butyric andt^i aShX'^ "^^^°^' ^^' ^^^^ ---t^ eonta:;;st;tS::nTe;:^^ ^^^ - ^^^-^ --^^^ ^^ -^o . _,, ,,, due t^r :;::::^^L^-^-^Ptie properties. .Heh .. medicinally in asthmadc and bronchTaia^ •""''''• '"^^ "'" ^^^« "^^^ under Chenncal Preparations, PaTt III ^ ^^'^""^- *'^- ^^so Eucalyptol, In connection with the ahn^-A ti.^ e n ■ have either been distinlro e.amL^^^^^ possess considerable interest: ^'^'''''^ '^-^' '^^^^s^s. Schimniel & Co., Oil of Backhausia cifnorTom TTo« „ i Specjflc g.a.it, 0.900. Boi,. ^J^^^ZXr'^^"^^'^''^ o.or. i^in-ai. ^ -JO L. It contains Oi/ o/ Eucalyptus amyadalina Sr>^.,-f: Optical rotation -27° to --68° ^-i ^"^ ^'"^""^^^^ <^-860 to 0.890 contains phellandrene and cineol. ""^ '''° ^^ ^^0° C- It 0/Z 0/ Eucalyptus Bayleyana fin^nift^ .".en leo. . J,, c. ,■; citai^tr, -rur '"''^ •-- ina^."^ ^"""'^'- '""•*™- Speoifle ^..,,,TZ, ^^,^^,^ O/Z o/ Eucahjpdus dealhata TT^^ « gravity 0.885 from fre.sh and 'o Sf? J^^^^^^a-like odor. Specific 206° and 216° C. ' ^""^"^ ^^^•^^' ^^^ves. Boils between ^p "^f Encahjptus Hcemastoma Ha^=,n^i oil. Specific gravity 0.890. Boils bett .-?'' '■'^""'''^^» ^^ ^"m^n tains c,,„o,e.„.. aMe.,.e, ^ f ^l.^ .::lr ^"° ' " ~- OiZ 0/ Eucalypttis macidata. Has a n^.i- r, gra^ty 0.900. Boils between 210° and oooo'^ ^^^"^^^^ ^^^r. Specific t-.oH,eO, and possibly geraniol —'^ ^. -it contains citronellal Boils between 209° and 2^0° C Tf . Slightly dextrogvrate. C,oH,.0, and geraniol C.oH./o. °' citronellal (citi-onellone) 0/7 of Eucalyptus microcorv^ q -^ t-.een ,60" and 2^- c. ItrSn, cCf '■""■•■^" "■'''■ ^^''^ "e- OFFICIAL ESSENTIAL OILS. 17 Oil of Eucalyptus rostratct. Specific gravity 0.924. Optical rota- tion -(-12° 58'. It contains cineol and valeric aldehyde. Oil of Eucaljiptus Staigeriana. Has a lemon-like odor. Si)ecifie gravity 0.880. Boils between 223° and 233° C^. It contains citral. Oil of Fennel. Oleum F(jeniculi. (Gcnnnn : Fenchel-Oel.) Distilled from the fruit of Fcenieuluia (■apiUufcuuL Ciilibert (Nat. Ord. Uuibelliferci'). "A colorless or pale yellowish liquid, having the characteristic, aromatic odor of fennel, and a sweetish, mild and spicy taste. Specific gravity not less than 0.960" (usually between 0.965 and 0.975, Schimmel & Co.). Its optical rotation varies between -|- 7° and -[-22°. "Between 5° and 10° C. it usually solidifies to a crj-stalline mass, but occasionally it remains liquid at a cousiilerably lower temperature." The higher the temperature at which crystals of anethol separate, the better is the quality of the oil. It contains pinene, phellandrene, dipentene, fenchone Cio Hio O, and anethol Cio Hi^ O, the latter usually in amounts of about 60 per cent. (Compare Oil of Anise.) The Oil of Fennel from different sources never contains all these constituents at the same time. Some, for example, contain no phellandrene, others no fenchone, and still others may contain no anethol. The medicinal action of Oil of Fennel is similar to tliat of Oil of Anise. Oil of Fleabane, see Oil of Erigeron. Oil of Gaultlieria. Oleum Gaultlieriae. [Oil of Wintergreen.] (German : Wintergreeii-Oel.) Distilled from the leaves of Gaultlieria p)rocumbens Linne (Nat. Ord. Ericacece), known also as CJieckerberri/, Partridge-herry or Boxherry. ' ' A colorless or yellow, or occasionally reddish liquid, having a characteristic, strongly aromatic odor, and a sweetish, warm and aromatic taste. Specific gravity 1.175 to 1.185. Boiling point 218° to 221° C. It deviates polarized light slightly to the left." Oils distilled in our Garfield factory we have found to vary in optical rotation from — 0° 22' to — 1°. The oil consists chiefly of methyl salicylate, with a fraction of 1 per cent, of another substance which has a peculiar odor, a viscid consistence, and high boiling point, and which is decomposed by distillation under ordinary pressure. The composition of the latter substance, which has been assumed to be a sesquiteijiene, has not yet been determined with sufficient accuracy. (See Pharm. Rundschau, 1889, p. 283; 1890, p. 38; also Amer. Jonrn. Pharm., 1889, p. 398; 1890, p. 9.) IS OFFICIAL ESSENTIAL OILS. Although Oil of Gaultheria is still accorded independent recognition by the U. S. Pharniacopdna, with i>robable deference to the more con- servative members of tlie profession, it is, nevertheless, a well known and recognized fact that most of the so-called X(it)i)-iile(jioi(lefi (Lvane) Persoon (Nat. Ord. Lahiatie). " A pale yellowish, limpid liquid, having a characteristic, pungent, mint-like odor and taste. Specific gravity 0.930 to 0.940." An oil distilled and rectified in our Garfield factory shows an optical rotation of -|-18° 43 , and a commercial oil from a reliable source -|-21° 20'. The oil has been chemically examined by E. Kremers (Proc. Amei'. JPJuu-m. Assoc, 1887, pp. 546-561), who found, after saponification ■with alcoholic potassa, an alcohol of relativelj" low boiling point, two bodies of the composition C,oH..O, boiling at 168° to 171° C, and 206° to 209° C. respectiveh', together with formic, acetic, and iso-heptoic acids. The bodies CioHisO were subsequently recognized as ketones, the higher boiling one being apparently menthone. It has also been shown more recentlj' that the oil contains pulegone do Hic O, and considered that the ketones previously mentioned represent tlie reduction products of the latter. {Phann. Rundschau, 1891, p. 130, and Proc. Wis. Pharm. Assoc, 1892. p. 55; 1893, p. 51.) An important test for the purity of this oil is its property of forming a clear solution with twice its volume of 70 per cent, alcoliol. Oil of Iledeoma has the properties of an aromatic stimulant, car- minative and emmenagogue. (Compare Oil of European Pennj/royal, below.) The following non-ofhcial oil, on account of its relationsliip with the preceding, may appropriately be considei-ed here: Oil of European Pennyroyal. {GcDntoi : Polcy-Oel.) Distilled froni the herl) of Mcntlia PuJegium Linne (Nat. Ord. Lahiato'). OFFICIAL ESSENTIAL OILS. 19 The oil has a yellowisli or j-ello\vish-green color, and a strongly aromatic, mint-like odor. Specific gravity 0.935 to 0.955. 02)tical rotation -(-18° to -\-2S°. The chief portion of the oil distills between 212° and 216° C, and contains pulegone, a ketone of the composition CioHisO. The latter is a colorless liquid, having an agreeable odor, reminding somewhat of pei^permint, boils at 130° to 131° C. under a pressure of 60 Mm., has a specific gravity of 0.9333 at 20° C, and optical rotation of -f-21° 16'. (Liebig's Annalen, Bd. 262, pp. 1-37, and Bd. 277, p. 160.) This oil, like the Oil of Hedeoma, is soluble in twice its volume of alcohol of 70 per cent, by volume, and also appears to possess analogous medicinal properties. Oil of Juniper. Oleum Juuiperi. (German : Wachhold(!rbeer-Oel.) Distilled from the fruit of Juniper us commiuiis Linne (Nat. Ord. Coniferce). " A colorless or faintly greenish-yellow liquid, becoming darker and thicker by age and exposure to the air, having the characteristic odor of juniper, and a warm, aromatic, somewhat terebinthinate and bitterish taste. Specific gravity 0.850 to 0.890 " (0.865 to 0-885, Schimmel & Co.). It is optically either dextrogyrate, lajvogyrate or sometimes inactive. It consists chiefly of pinene, with some cadinene C15H...1, and an undetermined substance, probably an ester, to which the peculiar juniper-like odor and taste are due. Oil of Juniper is used medicinally as a stinuilant, carminative and diuretic, but is chiefly employed in the j^reparation of certain liquors. • Oil of Juniper, Empyreuniatic, sec Oil of Cade. Oil of Lavender Flowers. Oleum Lavaudulve Florum. (German : Lavcndel-Oel.) Distilled from the fresh flowers of Lavandula officinalis Chaix (Nat. Ord. Labiatce). "A colorless or yellowish liquid, having the fragrant odor of lavender flowers. Specific gravity 0.885 to 0.897" (0.883 to 0.890, Schimmel & Co.). Optical rotation — 5° to — 8°. The oil contains linalool, linaloyl acetate, geraniol, and a very small amount of ciueol. The presence of the latter in any considerable amount would indicate a contamination with the Oil of Spike Lavender (see below). The oil should form a clear solution with three times its volume of 70 per cent, alcohol. The value of Oil of Lavender Flowers depends chiefly upon the amount of ester or linaloyl acetate which it contains, and wliich should 20 OFFICIAL ESSENTIAL OILS. not be less thau 30 to -W per cent. (See Schiinmel & ("o.'s BcricJif, April, 1893, p. 36, and April, 1894, p. 3G.) This estimation may be accomplished by the following method: (a) Determination of the Enter in Oil of Lavender Flotcers. About 5 grammes of the oil are accurately weighed in a strong glass bottle having a capacity of about 100 Cc, then 25 Cc. of alcoiiolic normal solution of sodium hydrate added, the bottle tightly corked, and allowed to stand for an hour in a batii of boiling water. After cooling, the free alkali is titrated, in the same bottle, with normal sulphuric acid, with the use of phenol-phtalein as an indicator. The number of cubic centimeters of alkali required for the saponification of the oil, when multiplied by the decimal 0.196, will indicate the amount of ester, calculated as linaloyl acetate Cio Hi7-C-. Ha Oj, con- tained in the weight of oil employed. (6) Determination of the free Linalool in Oil of Lavender Flou-ers. Into a long-necked flask, or one provided with a long glass tube, one end of which is so expanded and ground as to form a tightly fitting stopper for the flask, are brought about 10 Cc. of the oil, to- gether with 10 Cc. of acetic anhydride and 3 grammes of fused sodium acetate, and the mixtiu-e kept in a state of gentle ebvillition for two hours. After cooling, the mixture is shaken with 100 Cc. of water, and the separated oil washed by agitation with a 5 i^er cent, solution of sodium hydrate, being careful, by the gradual addition of the latter, to avoid any considerable elevation of temperature. This washing is con- tinued until, even after agitating the liquid for some time, it still retains a slightly alkaline reaction. The oil is subsequent!}^ washed with several successive portions of pure water, and, after sejDaration, it is dried by contact with calcium chloride, and filtered. Of this etherified oU, containing the linalool in the form of its acetic ester, about 5 grammes are accurately weighed, saponified, and titrated in precisely the same manner as described under (o). The amount of free linalool which may be calculated from the difference between the ester determinations (a) and (6) does not accurately rep- resent the amount actually contained in the oil, the latter being con- siderably greater, but the results, nevertheless, form a valuable basis for comparison. Oil of Lavender Flowers is used chiefly for its agreeable perfume. The following non-ofiicial Oils of Lavender maj- appropriately be considered here: Oil of Lavandula dentata Linne. Has a specific gravity of 0.926, and distills almost completely between 170° and 200° C. OFFICIAL ESSENTIAL OILS. 21 Oil of Lavandula Stoechas Linne. Has a specific gravity of 0.942, and distills between 1S0° and 24o° C. Botli of these oils have an odor reminding of rosemary and camphor, and contain ciueol. Oil of Lavender, Spike. {German: Spick-Ocl.) Distilled from the flowering herb of Lavandula sjnca D. C. (Nat. Ord. Labial ce). This oil is much less fragrant than the official Oil of Lavender Flowers, having an odor reminding of both rosemary and lavender, and it also differs in composition from the official oil. A pure oil should have the following characters: Specific gravity 0.905 to 0.920. Optical rotation 0° to -f 3°. It should form at 20° C. a clear solution with three times its volume of 70 per cent, alcohol. This test is of special importance for detecting adulterations with oil of turpentine. The oil contains piueue, camphene, ciueol, linalool, camphor, borneol, and possibly terpineol and gerauiol. (Compt. rend., 106, p. 5.")!; 117, pp. 53, 1094.) It is used chiefly in veterinary medicine, for liniments, etc. Oil of Lemon. Olenni Liniouis. (German : Citronen-Oel.) Obtained by expression fronx fresh Lemon Peel, the rind of the recent fruit of Citrus Linionuin. Risso (Nat. Ord. Rutacea'). ' ' A pale yellow, limpid liquid, having the fragrant odor of lemon, and an aromatic, somewhat l)itterish taste. Specific gravity 0.858 to 0.859 (0.857 to 0.860, Schimmel & Co.). Its optical rotation should not be less than 60 to the right in a 100 Mm. tube." The rotation of a pure oil usually varies from -(-60° to -|-64'- (See Schimmel 6 Co.'s Bericht, April, 1893, p. 22, and April, 1894, p. 24.) It contains a small amount of pinene, with dextrogyrate limonene, about 7 to 8 per cent, of citral (see the latter, vmder Chemical Preparations, Part III), and a small amount of citi'onellal {Bev. der deutsch. chem. Ges., 27, 1894, p. 354). The determination of the physical constantH, specific gravity and optical rotation, is of s^iecial importance for establishing the purity of this oil. Oil of Lemon is used chiefly as a flavoring agent and in per- fumery. Oil of Mustard, Tolatile. Oleum Sinapis Tolatile. (German : Seuf-Oel.) Obtained from Black Mustard, the seed of Brassica ni(jni (Linne) Koch (Nat. Ord. Cruciferce), by maceration with water and subsequent distillation. 22 UFP^ICIAL ESSENTIAL OILS. " A colorless or pah' yellow, limpid li(|Ui(l, haviuj^; a very pungent and acrid odor and taste. Specific giavity 1.018 to 1.029 (1.02 to 1.032, Schimmel & Co.). Boiling point 148° to 150° C." Optically inactive. It consists chiefly of allyl isosulphocyanate or allyl thiocarbimide C'S=N (C;) Ho), with traces of carbon disulphide. Its purity may readily be detei'niiued b}' the above mentioned character's, and by the other more extended tests described in the L". S. Pharmacopoeia, 1890. Volatile Oil of Mustard is used chiefly externally, and is an exceed- ingly p;)\verful irritant and vesicant. Oil of Myrciii. . OliMim ^lyrcisf. [Oil of Uay.] (German: IJay-Oel.) Distilled from the leaves of Myrcia acris DC. (Nat. Ord. Myrtacea'). "A yellow or brownish-yellow lic^uid, having an aromatic, some- what clove-like odor, and a pungent, spicy taste. Specific gravitj"" 0.975 to 0.990." The characters of this oil vary considerably, and this variation api)eai's to depend upon the season of the year in which the leaves are collected, or upon the age of the latter. From the results of a number of distillations we believe the specific gi-avity to be more correctly included within the limits of 0.965 and 0.985, being, how- ever, only exceptionally as low as 0.905, and generall\' ranging between 0.975 and 0.985. Some oils of our own distillation, as well as sami)les from the West Indies, yield a perfectly clear solution with an equal volume or more of ofl^cial alcohol, and this appears to be the case when distilled from relatively fresh leaves, while others, sometimes even of higher specific gravity, will afi'ord slightly turbid solutions. Our experience has also convinced us that the ofticial empirical test Avith sulphuric acid and dilute alcohol, as projwsed by Mr. Geo. M. Beringer (see Amer. Jouvn. Pliarm., 1888, pp. 441-445) for the discrimination or detection in this oil of the oil of cloves and oil of ])imenta, is totally unreliable, and no oil should be regarded as impure which fails tu conform to this test, if it has otherwise the proper characters. The oil, according to ^l\ttn\iiwa{Archiv dcr Pharm., 1889. \)\). 529- 548), contains terpenes, a considerable amount of eugenol, a little of tiie methyl ether of eugenol C. Ha (OCHs)- C3 H5, and apparently a diterpene Cjo Haj. A further investigation of this oil is now in progress in our Garfield laboratories. Oil of ]\Iyrcia is used as a refresliing perfume or lotion in the form of the popular P.ay Rum iSpirifHs Myrcia\ U. S. P.), or for perfuming soaps. Oil of Neroli, see Oil of Orange Flowers. OFFICIAL ESSENTIAL OILS. 23 Oil of Nutmeg. Oleum Myristicae. {Gcrma)i : Musksitnuss-Ocl .) Distilled from Nutmeg, the seed of ]\nji'isticeppermint, and a strongly aromatic, pungent taste, followed by a sensation of cold when air is drawn into the moutli. Specific gravity 0.900 to 0.920." OFFICIAL ESSENTIAL OILS. 25 For the distinctive color reactions, and the official test for the recognition of denientholized oil, reference may he made to the U. S. Pharmacopoeia, 1890. A quite extended investigation of Oil of Peppermint has been conducted in our Garfield laboratories, with special consideration of the chemical composition of the American oil, and the quantitative estimation of tlie menthol. The essential results of this investigation are here briefly summarized. The variations in the physical characters of oils from ditferent sources are shown in the following table: Source of Oil. 1. Our own distillation, from fresh Wayne Co., N. Y. , herl ) .' 2. Our own distillation, from partially dry Wayne Co. , N. Y. , herb '. ^ . 3. Our own distillation, from fresh, wild growing- herb (New Jersey) 4. Oil from Wayne Co., N. Y., new mint, first cutting, 1893 5. Oil from Wayne Co., N. Y., from crop of 1893. 6. Oil from St. Joseph Co., Michigan, new mint, first cutting, 1893 7. Oil from St. Joseph Co., Michigan, new mint, second cutting. 1893 8. Oil from Van Buren Co., Michigan, new mint, first cutting, 1893 9. Oil from Wayne Co., Michigan, new mint, first cutting, 1893 10. Oil from Mississippi 11. Saxon Oil, from herb grown and distilled by Schimmel & Co., Leipzig 12. Mitcham Oil. Rectified. 13. Japanese Oil 14. Japanese Oil, partially deprived of mentliol. . . . Specific Gravity at 1.5° C. 0.9130 0.9140 0.9150 0.9110 0.9158 0.0135 0.9083 0.9067 0.9135 0.9250 0.9100 0.9070 0.9100 0.9030 Optical Rotation in m) Mm. Tube. —30° 0' —32° 0' —22° 55 —32° 30 -2(5° 45' — 9° 45 —19° 30' —29° 20' — 2S° 30' —13° 40' —2(3° —27° 55' —34° 45' -31° 20' The deportment of the oils on fractional distillation affords an excellent criterion of their character, as oils originally of abnormal com- position, as well as those which have lieen more or less deprived of menthol, or which contain the ordinary adulterants, may thus quite readily be recognized. The results of a single fractionation of 50 Cc. of various oils, conducted under conditions as nearly identical as possible, and with the mercurial column of the thermometer entirely in the vapor, are presented in tlie following table. The figures represent the number of Cc. of liquid which distilled over at the specified 26 OFFICIAL ESSENTIAL OILS. temperatures, but wliich would naturally be materially changed by repeated fractionation. Designation of To 200° 200-2a5" 205-210» 210-215° 215-220° 220-22-5° 1 225-230° 230-2a5° Oils. C. c. C. C. C. 1 c. C. C. 1 A. 1.1 1.4 5.6 10.0 12.9 8.0 3.1 2.0 B. 2 2 5.7 9.8 vi:6 11.3 2.8 0.5 C. 0.9 0.8 1.3 6.5 16.2 11.8 4.8 2.4 D. 0.7 0.4 3.4 22.0 17.2 2.1 1.0 E. 0.5 1.6 10.2 20.7 12.0 3.3 F. 1.4 0.7 12.2 24.7 8.6 A represents the average of the figures obtained from quite a series of American oils, which agreed very closely among themselves, as also with the oil of our own distillation, and to a certain extent represent the nomial tjiies of American Peppermint Oil. i? • represents the average of the figures obtained from three Michigan Oils, indicated in the preceding table by the numbers 6, 7 and 8. C represents a MLssissijjjn Oil, denoted in the preceding table as number 10. This is characterized by the remarkably large amount of liigher boiling constituents, as also by its high specific gravity. Although these three groups may be considered to possess some points of similaritj-, thej^ will be seen to be totally different from the three next following, which are much richer in menthol than the American oils. D represents a normal Japanese Oil. E represents a Japanese Oil, partially deprived of menthol. F represents a Rectified Mitcham Oil. The results of a chemical investigation, conducted in our Garfield laboratories, have thus far shown that American Oil of Peppermint contains the following bodies: 1. Acetaldehyde, CH3-COH. 2. A eft iu acid, CHs-COOH. 3. Iso-valeraldchyde, (CH:i)2CH-CH2 COH. 4. Iso-valeiianu' acid, (CH3)2 Cn-CH2 COOH. Boiling- point 5. A liquid acid, 6. Pincnc, T. PhoUandrenc, 8. Limoncne, 9. Cincol, 10. Mcnthone, 11. Menthol, 12. Mcnthyl acetate, 13. " iso-valcrianate, 14. Cadincnc, 1."). .\ lactone. r.sHl2 02. ClO H16. Cio Hic. Cio Hic. C10H18O. Cio His O. C10H19-OH. C10H19-C2H3O2. CioHi9-Cr, H..O2. Ci.. H2.1. C10H1CO2. (COIT.). (corr.). about 275° Meltinu- iidiiit OFFICIAL ESSENTIAL OILS. 27 The lactone may be converted into a colorless, well crj-stallizable oxy-acid C10H18O3, which melts at 93' C. The hydrocarbon menthene doHif, wliich has been stated to occm- in Russian Peppeimint Oil, although apparently without suf- ficient proof, we have not been able to detect in the American oil. Although the previously mentioned physical characters of Oil of Peppermint, such as specific gravity, optical rotation, and especially its deportment on fractional distillation, or by exposure to cold, may serve as a criterion of the quality of the oil, and were in fact hitherto the only available means of judging of its purity, a much more exact and satisfactory method of valuation is afforded by the quantitative determination of the essential constituent of the oil, which is the menthol. The researches conducted in oiu- Garfield laboratories have led to the formulation of such a method, which is not only quite simple in execution, but also indicates with remarkable accuracy, as controlling experiments with pure menthol have shown, the amount of menthol which is actually contained in the oil. VALUATION OF OIL OF PEPPERMINT. Based on the quantitative determination of the menthol. {a). Estimation of tJie menthol contained in the form of ester. About 20 grammes of the Peppermint Oil are accurately weighed in a strong glass bottle having a capacity of about 100 Cc. 30 Cc. of alcoholic normal solution of sodium hydrate are then added, the bottle tightly corked, and allowed to stand for an hour in a bath of boiling water. After cooling, the free alkali is titrated, in the same bottle, with normal sulphuric acid, with the use of phenol-phtalein as an indicator. If there are required for this purpose a Cc. normal acid, and if S represent the weight of oil used, then the percentage of menthol P contained in the oil in the form of ester may be calculated by the following formula: ^r^ j^(> (30— o) (fi). Estimation of the total meidhnl, free and combined. The total liquid obtained in the preceding estimation is thoroughly shaken in a separating funnel with 100 Cc. of water. After the sep- ai-ation of the oil the aqueous liquid is drawn off, and the oil washed in a similar manner by shaking it with three successive portions of water of 100 Cc. each, for the purpose of removing the alcohol. The washed oil, carefully separated from the water, is then brought into a flask having a capacity of 100 to 150 Cc, and jDrovided with a long glass tube, ground at one end to fit the mouth of the flask and serve as a condenser, or otherwise a simple long-necked flask may be used. 28 OFFICIAL ESSENTIAL OILS. To the oil are then added "2(1 Cc. of acetic anliydride aud 2 grammes of fused sodium acetate, and tlie mixture kept in a state of gentle ebullition for an hour. After cooling, the mixture is shaken with 100 Cc. of water, and the separated oil washed by agitation with a 5 ]>er cent, solution of sodium hydrate, being careful by the very gradual addition of the latter to avoid any considerable rise of temijerature. This washing is continued until, even after repeated agitation, the liquid retains a slightly alkaline reaction. The oil is subsequently waslied with several successive portions of water, aud, after separation, it is dried by contact Avith calcium chloride, and filtered. Of this acetylized oil, containing the menthol in the form of its acetic ester, about 8 to 10 grammes are accurately weighed in a strong glass bottle, 50 Cc. of alcoholic normal solution of sodium hydrate added, the bottle tightlj' corked, and allowed to stand for an hour in a bath of boiling water. After cooling, the free alkali is titrated, in the same bottle, with normal sulphuric acid, wnth the use of i)henol- phtalein as an indicator. If there are required for this i)urix)se h Cc. of normal acid, and if s represent the weight of acetjiized oil used, then the total 2)ercent(ige of vieiithol V, free and combined, maj' be calculated by the following formula : P' = (oO—b) 15.56 \s— 0.0419(50— ?y). The application of this method to the vai-ious oils i^reviously noted lias afforded the following results: Designation of Oii, Menthol in form of Ester. Total Menthol. 1. Our own distillation, from fresh AVavne Co., N. Y., herb ". 11.03$» 2. Our own distillation, from partiallv dry Wayne I Co., N. Y., herb .'....' | 13.84j? 3. Oil from Wavne Co., N. Y., new mint, first cut- ting, 1893.' 8.42^ 4. Oil from Wayne Co., N. Y., from crop of 1893. 9.14,^ 5. Oil from St. Joseph Co., Michigan, new mint, first cutting, 1S93 3.56^? 6. Oil from St. Jose])h Co., Michigan, new mint, s(>coni'<>duct, as its misleading name would imply, but is evidently obtained by the fractionation of camphor oil. As the essential and predominating constituent of Oil of Sassafras is safrol, the advantages of the latter in a pure forni are sufiiciently apparent. Oil of Sassafras is used chiefly for perfuming ordinary soaps, and for imparting flavor to beverages, etc. Oil of Saviiie. Oleum SaMuae. (German : Sadebavim-Oel.) Distilled from the tops of Juniperus Sabina Linne (Nat. Ord. Conifer(P). "A colorless or j^ellowish liquid, becoming darker and thicker by age and exposure to the air. It has a peculiar, terebinthinate odor, and a pungent, bitterish, and camphoraceous taste. Specific gi-avity 0.910 to 0.940" (0.905 to 0.930, Scliimmel & Co.). Optical rotation -|-40° to +50°. It contains pinene, and cadinene dsHv,. Oil of Savine is used medicinally as a stimulant, enunenagogue, and rubefacient. OFFICIAL ESSENTIAL OILS. 33 Oil of Spearmint. Oleum Meuthsv Viridis. (German : Speermiiiz-( )l'1.) Distilled from the fresh herb of MentJia viridis Liune (Nat Onl. Lahi((t(e). "A coloi'less, yellowish, or greeuish-yellow liquid, Ijecoiniiif; darker and thicker by age and exposure to the air, having the characteristic, strong odor of spearmint, and a warm, aromatic taste. Specific gravity 0.980 to 0.94!)" (0.920 to 0.940, Schimmel & Co.). The oil contains la^vogyrate carvol and hevogyrate limonene, with jwssibly some laevogyrate pinene. (Compare Oil of Caraway.) Oil of Spearmint i.-i used medicinally as an aromatic stimulant and carminative, and is also eini)loyed for perfuming soaps. Oil of Sweet Birch, see Oil of Betiila. Oil of Tar. Oleum Picis Liquidje. (German: Theer-Oel.) Distilled from Tar, an empyreumatic oleoresin obtained by the destructive distillation of the wood of Pinus jpalustris ]\Iiller, and of other species of Pinus (Nat. Ord. Coiiiferce). "An almost colorless liquid when freshly distilled, but soon ac(j[uiring a dark reddish-brown color, and having a strong, tarry odor and taste. Specific gravity about 0.970." This oil is a complex mixture of hydrocarbons, acetic and other acids, and undetermined empyreumatic products present in tar. It has the medicinal properties of tar, and is used chiefly in diseases of the skin. Oil of Thyme. Oleum Thymi. (German : Thyinian-Oel.) Distilled from the leaves and flowering tops of Thymus imlgaris Linne (Nat. Ord. Labiatce). ' ' A yellowish or yellowish-red liquid, having a strong odor of thyme, and an aromatic, pungent, afterwards cooling taste. Specific gravity 0.900 to 0.930." Messrs. Schinmiel & Co. haye found Oil of Thyme of their own distillation to vary in specific gravity, according to its source, as follows : From fresh herb, German 0.925-0.935. " dried " " 0.909-0.928. " fresh " French 0.934. (tultivaiod ill Sa.xonj) " dried herb, French 0.909-0.918. " herb, Spanish 0.925-0.950. 34 OFFICIAL ESSENTIAL OILS. The most iinportaut coiistitueut of Oil of Tliyine is tliyinol (see tiie latter, under Chemical Preparations, Part III). In some oils, however, there is found, instead of thymol, the isomeric carvacrol, and in others the two phenols occur in nearly etjual amounts. Other constituents are cymol, and very small amounts of bornjl esters. The oil should form a clear solution with half its volume of alcohol (distinction Irom oils irhu'li have been deprived of their phenols). Oil of Thj'me is used chiefly as an external stimufant, in Ihii- nients, etc. The following non official, but closely related oils, may convenientlj' be considered here; Oil of Thyme, AVild {Oleum Serpylli). (German : Feldthymian-Oel.) Distilled from the dry herb of Thymns Serpylliim Liime (Nat. Ord. Lahiatce). This oil has a very agreeable, melissa-Iike aroma, with a slight odor of thyme. Specific gravitj- 0.917. Optical rotation —10" 20. It con- tains thymol and carvacrol. Tliis oil should not be confused with an oil distilled in .southern France, known as " f^ssence de Serpolet,"' which is of uncertain origin, and has an odor reminding more of pennyroyal. Oil of Tliymus camphondns has a specific gravity of 0.004 and contains carvacrol. Oil of Thynuis ccqnfcdus, distilled in southern Spain, has a strong thyme-like odor, reminding somewhat of origaiuun. Si)ecific gravity 0.901. It contains i)iuene, cymol, dipentene, bornyl acetate, thymol, and ])n)l>nbly carvacrol. Oil of Turpentine. Oleum Terebinth injp. {GrrmiDi : Teri)L>iitiii-()el.) Distilled from American Turpentine, a concrete oleoresin obtained from Piiius j'tdustris ^liWw, ami from other species of Pintifi (Nat. Ord. Conifera'). "A thin, colorless liquid, having a charactei-istic odor and taste, both of which become stronger and less pleasant by age and exposure to the air. Specific gravity 0.855 to 0.870 " (0.855 to 0.876, Schimmel & Co.). It deviates polarized light to tiie right (distinction from French Oil of Turpentine). "Boiling point between 155 and 170' C. It is .soluble ill '.] times its volume of alcohol, and in an equal volume of glacial acetic acid." OFFICIAL ESSENTIAL OILS. 35 Oil of Turpentine, Rectiftetl. (German: Rectiflcirtes Terpciitin-Oel.) Oleum Terebinthime Rectiftcatuni. This oil, purified from resinous matter and other oxidation prod- ucts according to the directions of the Pharmacoj^ceia, is the only form in which Oil of Turpentine is suitable for internal use. "It is a perfectly colorless liquid, having a mild odor, and the general prop- erties mentioned under Oil of Turpentine. Specific gravity 0.855 to 0.865. Boiling point about 160 C." 10 Cc. of the freshly rectified oil, ^^•hen evaporated on a water bath, should leave a residue weigliing not more than about 0.03 gramme. The oil consists chiefly of dextro- gyrate pinene. Oil of Wintergreen, Natural, see Oil of Gaultheria. Oil of Wiutergreen, Synthetic or Artificial. [Methyl salicylate.] ^j^^j^ j SalicjlaS. (German: AVintergreen-Oel, Synthetisch.) (CH-)C- H- () "A colorless or slightly yellowish liquid, having a characteristic, strongly aromatic odor, and a sweetish, warm, and aromatic taste. Specific gravity 1.188 to 1.185 (when perfectly free from water, 1.187). Boiling point 219" to 221 C. It is optically inactive. "If to 1 Cc. of Methyl Salicylate, contained in a capacious test tube, 10 Cc. of a 5 per cent, solution of sodium hydrate be added, and the mixtvire agitated, a bulky, white, crystalline precipitate will be pro- duced; then, if the test tube, loosely corked, be allowed to stand in boiling water for about five minutes, with occasional agitation, the precipitate should dissolve, and form a clear, colorless or faintly yellowish solution, without the separation of any oily drops, either on the surface or at the bottom of the liquid (absence of otliei' volatile oils or of x>etrolexim). "If the alkaline liquid thus obtained be subsequently diluted with about three times its volume of water, and a slight excess of hydro- chloric acid added, a white, crvstalline precipitate will be produced, which, when collected on a filter, washed with a little water, and recrystallized from hot water, should respond to the tests for identity and purity of salicylic acid (absence of metlii/l benzoate, etc.)." Synthetic Oil of Wintergreen was first i)repared on a large scale and brought into commerce by Messrs. Schimmel & Co., of Lei[)sic, and it is now also manufactured extensively in our Garfield factory. Being a definite chemical compound, and readily obtainable in a state of perfect purity, it has rapidly, and to a large extent, displaced the 36 OFFICIAL ESSENTIAL OILS. "^^ natural oils of \nrvh and gaultheria. The two latter oils, being pre- pared mostly by itinerant distillers, are also much more subject to adulteration than the synthetic product. For a review of some of the fallacious tests which have been assumed to discriminate between the .synthetic and natural oils, eee Pliarm. Rundschau, N. Y., 1893, pp. 7-9. (Compare also Oil of Betula and 0(7 of Gaidtheria.) Synthetic Oil of Wintergreen is used chieHy as a flavoring agent. Oil of Wormseed, American, ^cc Oil of Clieiioi»oilium. PART II NON-OFFICIAL ESSENTIAL OILS. The Oils included in the following List are not recognized by the United States Pharmacopoeia, Seventh Decennial Revision, 1890. Many of them, however, are of Commercial Importance, while others must be regarded at present as possessing chiefly Scientific Interest. Oil of Achillea coronopifolia. Distilled iu Spain from the flowering herb. The oil is limpid, has a deep l^lue color, and a strong, agreeable odor, reminding of oil of tansy. Specific gravity 0.924. Oil of Achillea Millefoliuin, see Oil of Milfoil. Oil of Achillea moschata, see Oil of Iva. Oil of Amber, Rectified. {Gi'niiai>: Rectificirtes Rernsteiii-Oel.) An empyreumatic oil obtained from Amber, the latter being a fossil resin from Pinites snccinifei' Goeppert, and other extinct conif- ei'ous trees. This oil was recognized by the U. S. Pharmacopoeia, 1870, under the title Oleum Succini Rectijlcatuiii, and was described as "a color- less or pale yellow, thin lifjuid, becoming darker and thicker by age and exposure to the air, having an empyreumatic, balsamic odor, and a specific gravity of about 0.920." We have found the specific gravity of the crude oil to be aljout 0.975, and that of the rectified oil 0.915. A normal rectified oil is not colorless, but possesses a brown color, becoming darker l)y age. The oil consists chiefly of a mixture of hj'drocarbons, with some phenols. It is rarely employed medicinallj', and chiefly externally in the form of liniments. 38 NONOFFICIAI. ESSENTIAL OILS. Oil of Aiiibrette Seed. {(It riiKtii : M()si'lui.*kuiiiaratioiis, l*art IIL Oil of Arbor Vita', sec Oil of Thuja. Oil of Arnica Flowers. (Gcnium : Arnicabliithen-Oel.) Distilled from the flowers of Arnica luontaud Linue (Nat. Ord. Contpositd'). The oil is usually of a yellowish color, becoming brown with age, and has a strongly aromatic odor and taste. Specific gravity 0.900 at 25' C. The physical characters of the oil are subject to considerable variation, depending ujjon the amount of stearopten or paraffin-like bodies present. Thus, while the oil is sometimes licjuid at ordinary temperatures, solidifying only in winter, the jiroduct of other distil- lations forms at lo' to 20" C. a butter-like mass (see Scliimmel & Co.'s Bericht, April, 1894, p. 9). The oil appears not yet to have been chemically examined. Oil of Arnica Root. {(ii-niuni : Ar.'iieawurzel-Ool.) Distilled from the root of Arnica montana Linne (Nat. Ord. Composit(c). The oil has a yellow color, becoming darker witli age, a strong odor, and sharp, aromatic taste. Specific gravity 0.990 to 1.0. It contains about 80 per cent, of the dimethyl ether of thyniohydro- quinone, Ci„ Hij (OCH:,).,, and 2) per cent, of phlorol iso-butyric ester, C^IIi-COOCHo, Avith a very little phlorol-methyl ether, CsHs- OCHa. The oil is occasionally used medicinally. Oil of .Vrteniisia Absinthium, see Oil of AVornnvood. Oil of Artemisia Barellieri. Distilli'd ill soutiiern Spain from the flowt-riiiu," herb of Artfiin'sia BarcUieri Doiss. (Nat. Ord. Couqmsifte.) The oil has an agreeable and strongly aromatic odor, reminding of tansy. Specific gravity 0.923. It boils between 180' and 210° C. Oil of Artemisia Dracunculus, s( c Oil of Estragon. NON-OFFICIAL ESSENTIAL OILS. 41 Oil of Artemisia giacialis. (German : Alpenbelf uss-Ool.) Distilled from the herb of Artemisia glacialin Luc, the so-called Genepi des Alpes (Nat. Ord. Composita-). The oil has a strongly aromatic odor. Specific gravity 0.964 at 20° C. It solidifies at 0" to a butter-like mass, which is due to the presence of a fatty acid having a melting point of Gl ('. The oil boils between 195" and 310 C. Oil of Artemisia maritima, see Oil of Wormseed, Levant. Oil of Artemisia viilacaris. (Gi'iiiian : Beif uss-( )t'l.) This oil has been distilled both from the hei-b and the root of Artemisia vulgaris Linne, or common Mugwort (Nat. Ord. C'ompnsitce). The oil from the herb has a specific gravity of 0.920, but has not been further examined. Oil of Asafetida. (German: Asaf(jetida-Oel.) Distilled from Asafetida, a gum resin obtained frt)m the root of Ferula foetida (Bunge) Regel (Nat. Ord. Umhellifene). The oil has a light yellow color, and the penetrating, disagreeable odor of the drug. The specific gravity has been observed to be in one specimen 0.9789 at 12° C, and in another 0.9843 at 22' C. (Semmler), or 0.98o at 1")" C. (Schimmel & Co.), and 0.9515 at 25' C. (Fliickigeri. Optical rotation — 9" 15 (Semmler), or -\-lS' to +19" (Fliickiger). The oil is stated to contain two terpenes CjuH,,;, a ))ody of the composition Ci I, Hi G O, which yields a sesquiterpene Ci 5 Hj4, the sulphur compounds CtHhS-j and CnH^oSo, and a blue colored oil in the higher boiling portions. (Semmler, Bcr. d. dentscJt. chrm. Ges., 1890, p. 3530. and 1891. p. 78.) Oil of Asariim Caiiadeiise. (German : Canadisclie-Schlan^cnwurzel-( )ol.) Distilled from the rhizome and roots of Asarum C'anadense Linne, "Canada Snake Roof (Nat. Ord. Aristolochiacece). The oil has a yellowi.sh or }-ello wish- brown color, and a strong, agreeably aromatic odor and taste. Specific gravity 0.930 to 0.960. It contains a small amount of a terpene (about 5 per cent.); an alcohol C10H17-OH, boiling point 197" to 199^ C, termed asarol, probably identical with linalool (about 35 per cent.); an alcohol 42 NON-OFFICIAL ESSENTIAL OILS. C10II1--OH, boiling point ••2',':J to 220 C, liaving a geranium-like odor (about 15 per ceui;.); the methyl ether of eugenol CeHsiC'aHs) (OCH;,)j (about 3.") per cent.); acetic and valerianic acids, as esters of the above mentioned alcohols; and a high boiling fraction of a deep blue color (about 10 per cent.), but no dsarone. {Proc. Amer. PJiarin. Assoc, 1880, pp. 464-485; Pharm. Rundschau, 1888, p. 101; Bcr. d. dcufsch. chevi. Ges., 21, ]>. 1004.) Compare also Oil of Asarniu EiiropiPJim. The oil forms a clear solution with twice its volume of TO per cent, alcohol. It is of value in perfumer}'. Oil of Asaruiu EiiropjiMiin. {(icrinint: Asarvim-Ocl oi- Ilaselwurz-Oel.) Distilled from the rhizomi? and roots of Asarxin Europceum Linne, " Asaral)acca" (Nat. Ord. An'stoloclildcea'). A somewhat thick, brownisli liquid, having a sweetish-aromatic odor. Spec-ific gravity 1.046 to 1.068. It contains pinene; the methyl ether of eugenol Co H3 (C3 H5) (0CH:,)-2 ; asarone Or. Ho (C3 H5) (OCH:,)^ ; and a high boiling fraction of a bluish color, but no asarol (Arcliiv der Pharm., 1888, pp. 89-123, and Ber. d. deutsch. diem. Ges., 21, pp. 1057-1063). Compare also 0(7 of Asarinn Canadense. Oil of lialsaiii Peru. {Gcnnan: Peru I5:ils:iin-(^cl.) Distilled from the balsam of Toluifera Pereine (Royle) Baillon (Nat. Ord. Leyuminosfe). A light colored li([tii(l. liaviug an agreeahly aromatic odor, re- minding of Balsam of Peru, of which it is the chief constituent. It consists for the most part of "cinnamein," the benxyl e.sters of cinnamic and benzoic acids. According to Trog (ArcJiiv der PJtarm., 1894, pp.' 70-98), the liquid portion of Balsam of Peru consists chiefly of benzyl benzoate, C-, H7 (C7 H^ Oo), with only a very small amount of benzyl cinnamate, C: H; (C, H, O,). The oil is used in ])erfumeiy. (HI of Balsam Tolii. {GeniiiOi: Tolu Halsum-C )el.) Distilled from the balsam of Toluifera Balsamum Linne (Nat. Ord. Leynininosce). The oil has a very agreeable, hyacinth-like odor. Specific gravity 0.935 to 0.975. It contains a terpene C,„H,fi, and esters of cinnamic and benzoic acid. The oil is of value in perfumery. NON-OFFICIAL ESSENTIAL OILS. 43 Oil of Basilieiiin oi* Eiirll. (GcruHin : Uiisilicuui-OcI ) Distilled from the lierh of Oc/pnu)ii Biniliciuit Linne (Nat. Ord. L(tbiata'). The oil has an aromatic odor. That fro: a fresh German herb has a specific gravity of 0.918 to ().'J28, wliile tiiat from Reunion is 0.946 to 0.967, and has an optical rotation of -|-1*^ ■ The oil has not yet been chemically examined. Oil of Beecli Tar. (Gtvmaii : Bufhciithcer-Oel.) Obtained by the fractional distillation of Beech Tar, the latter being a product of the dry distillation (jf the wood of Fagnu sdva- tica Linne (Nat. Ord. Ciqndifera'). The ligJtt oil, which is usually employed, has a sjiecitic gravity of 0.980, and distills between SV and 2.j()' C. The main portion distills between 150" and 2o0' C, and consists of from one-third to one-half of phenols and phenol-ethers. The lieai-ij oil has a specific gravity of l.Oo:! It distills between 320° and 300' C, and contains about 66 per cent, of phenols. Oil of Beech Tar has been used in lung diseases. Oil of Betle Leaves. {German: Betel-Oel.) Distilled from the leaves of Piper Betle Linne (Nat. Ord. Pipenieew). The oil has a light brown color, an agreeable tea-like odor, and a burning taste. The oil of dried leaves from Siani has a specific gravity of 1.034, that of fresh leaves from Manila 1.044, and that of fresh leaves from Java 0.958, and an optical rotation of -(-3" 53'. The oil contains betle-phenol or para-eugenol CoHa (Cs H5)(OH)(OCH3), cadinene CisHai, and sometimes para- allyl-i^henol or chavicol Ce H4 (0H)(C3 H.,). (See Schimmel & Co.'s Bericht, April, 1890, p. 6, October, 1891, p. 5, and Journ. filr praM. Cheniie, N. F., 1889, p. 349.) Oil of Birch Tar {Olema Jiusci). (German: Roctilieirtes Birkontheer-Oel.) Distilled fi"om Birch Tar ((7er»Hni ; Juchten-Oel), the latter being a product of the dry distillation of t!ie wood of Bit aid ((Uxiluinne (Nat. Ord. Cupuliferce). A yellowish- brown liquid, having a characteristic odor, like that of Russia leather. Specific gravity about 0.956. It contains about 40 44 NON-OFFICIAL ESSENTIAL OILS. jK.'r ct'ut. of ])heuols, wliich hoil l)et%veeu 180" aud 250 C, aud cunsidt chiefly of guaiacol aud creosol, with small amounts of cresol aud xylenol. Tlie portiou insoluble in alkalies l)oils lietween 170' and 288 C. (See Scliimmel & Co.'s Berichf. April. 1891, p. 6. aud An-hiv (let- Phanii.. 1890. j). 7i:l) Oil of lioldo Leaves. (Geruuui : BokloblStter-Oel. Distilled from the leaves of Boldoa fragraiis Gaj' (Nat. Ord. 3Iou im iacecv). Tlie oil has a reddish yellow color, the pepper-like, narcotic odor of the leaves, and a inild, herby taste. Specific gravity 0.918 to 0.945. It boils between 175 and 250 C;., and contains terpenes aud oxygenated bodies. Tlie oil has been used medicinally in affections of the liver, dys- pepsia, rlieumatisTu, etc. Oil of Biigle Weed. {(Icniiaii : Lyi!Oi)us-Oel.) Distilled from the dry herb of Lycopns Virginicus Linne (Nat. Ord. Ldhidtd'). The oil has a cliaracteristic odor, which is difficult to define. Specific gravity 0.924. It has not j'et been chemically examined. The herb is said to possess mild narcotic properties. Oil of IJucliu. {(jcriiuin : JBuecublSttcr-Ool.) Distilled from the leaves of Barosma serratifoUd Willdenow and Barosma hetulitut Bartling (Nat. Ord. lintacece). The oil has a strong mint-like odor. That from B. sermtifoUa has a specific gx'avity of 0.944, and contains but little of the crystal- lizable diosphenol CioHmOa. The oil from B. betnlina contains a large amount of diosphenol, and, after the separation of the latter at ordinary temperatives, has a specific gravity of 0.969. There is also present in the oil a bod}^ of the composition CioHisO, having a peppcrmiut-like odor. Oil of ("alaiiius {(irriiKUi : Caliinis-Oe'l.) Distilled from the rhizome of Acorns CaloDi.ns Linne, "Sweet Flag' (Nat. Ord. Aroidece). A clear, somewhat thick, brownish-yellow liquid, liaviug a strongly aromatic odor, and an aromatic, bitter taste. The oil from fresh Gennan calamus has a specific gravity of 0.960 to 0.970, aud au NON- OFFICIAL ESSENTIAL OILS. 45 optical rotation of -j-SO to +31 > wliile tliat from the dry drug lias a specific gravity of 0.960 to 0.980, and an optical rotation of -(-15 ' to -\-2V. The oil appears to contain piuene and a sesquiterpene, a body of the composition Cio Hi 6 O, a high boiling fraction of a bluish color, and a very small amount of a phenol. Oil of Calamus is used to a small extent medicinally as a tonic and carminative, but chiefly in the preparation of liquors. Oil of Japanese Calamus is characterized by a higher specific gravity, 0.985 to 1.00, and by its much greater solubility in dilute alcohol. Oil of Camphor. (GcrhKiii : ( 'umphor-Oel.) The crude Japaiiese Camphor Oil is obtained as a by-product in the preparation of common camphor, by the distillation of the wood of Cinnamomiivi. C\tm}>h<)ra. fLinne) Nees et Ebermaier (Nat. Ord. Lauracea'). It is an exceedingly complex substance, and contains, according to the researches conducted in the laboratories oi Messrs. Schimmel & Co., of Leipsic, the following bodies: Pinene, Ci,, His Boiling point 158-162" C. Phellandrene, CioHu; " " about 170" C. Cineol, CoH.sO " " 176" C. Dipentene, Co Hi,-, " " 180° C. Camphor, C, „ H, „ O " " 204' C. Terpineol (?), Co Hi, - OH " " 215-218° C. Safrol, CoHioOo " " 232° C. Eugenol, CoHi,0, " " 248° C. Sesquiterpene (Cadinene), Cis H-ji " " 274° C. By fractional distillation the original crude oil affords the com- mercial Light Camphor Oil, specific gravity about 0.920, and the so-called Heavy Cainphor Oil, specific gravity aliout 0.970. Messrs. Schimmel & Co., of Leipsic, have also distilled in their own factory, from crude material obtained from Japan, the following: Oil of Camphor Leaves and Oil of Camphor Koot. Both of these oils contained a large amount of camphor, and the liquid portion separated thei'efrom has the properties of the above mentioned, ordinary camphor oil of commerce. Oil of Canada Snake Root, see Oil of Asarnni Canadense. 40 NON-OFFICIAL ESSENTIAL OILS. Oil of Caiiaiiiia, Java. i'Jeiman : Caiiunsa-Oel, Java.) Distilled from the flowers of Caiiamjn odoratii Hooker lil. et ThoinsoM (Nat. Ord. Aiionaceo'). The Cananga flowers are tnown by the natives of the South Sea Islands as "Mosoi." The oil has a yellowish color, and an exceedingly agreeable odor; which renders it valuable as a perfume. The odor, however, is not nearly so delicate as that of the so-called "Ylang- Ylang Oil," which is distilled in JIauila from the same plant (see Oil "of YhiiKj-Ylaiif) ; also Sc-himmel & Co.'s Ben'clit, October, 1887, p. 7, and " Odorographia "' by Sawer, p. 117). Oil of Cananga has a specific gravity of 0.910 to 0.920. It con- tains an ester of benzoic acid. Oil of Caiiella. {Ucrmaii : Canella-Oel or Weisszimuit-Oel.) Distilled from the bark of Candid alha INIurray (Nat. Ord. Canel- lacece). The oil lias a spicy t)dor and taste. Specific grayity 0.922. It contains cineol and eugenol. Oil of Cartlainom. (dermmi : C"arihiiuonien-()el.) Distilled frfan the seed of Ehtttaria rcpens (Sonnerat) Baillou (Nat. Ord. Scilaniiuece). Tlie oil has a pale j-ellow color, and a stronglj' aromatic, some- what camphoraceous odor and taste. Si^ecific gravity 0.895 to 0.905. Optical rotation about -|-13". It contains terpinene, possiblj' dipeutene, a body of the composition CioHi^O (terpineol '?), and acetic and formic acids. The oil affords a clear solution with one or more i)arts of 80 per cent, alcohol. Oil of Cardamom is u.sed chieHy in tlie preparation of licpiors. Oil of Carliua. {(Icrmnn : Eberwurz-Oel.) Distilled from the root of CarliiHi (u-avlis Linue (Nat. Ord. ('<))u- 2)0sitce). The oil has a dark reddisli-bro\\u color, and a narcotic odor. Specific gi'avity 1.033 to 1.036. Its constituents have not yet been determined. Oil of Carrot, ^Vild. (German : Daucus-Oel or ^^ohrensamerl-Oel.) Distilled from tlie fruit of Danciiif Carota Linne iNat. Ord. Z''))ibeUifer(i'\. NON-OFFICIAL ESSENTIAL OILS. 47 It has a yellowish color, au agreeable earrot-like odor, aud a sharp taste. Specific gravity 0.87 to 0.93. Optical rotation — 1'3 . It con- tains pinene, and a body of the corof)Ositiou CioHisO, which is possibly <'ineol. Oil of VsiHCA preciosa. {German: Casoa prociosa-Oel.) Distilled from the bark of MespiJodnphne pretiuaa N. et M. (Nat. Ord. Lariracea']. It has a strong ciunanion-like odor and a bnruiug, aromatic taste. Specific gravity l.llS. It has not j'et been thoroughly examined, but appears not to contain cinnamic aldehyde. Oil of C'asearilla. (German : Cascarill-Oel.) Distilled from the bark of Croton Eluteria Bennett (Nat. Ord. Eiiph orbiacere). It has a greenish or dark yellow color, and a i)urely aromatic odor and taste. Specific gravitj' 0.890 to 0.930. It has not yet been sufficiently examined chemically (see Liebig's Annitlni, Bd. 35, p. mri Oil of Catnip. {German : Katzenminz-Oel.) Distilled from the herb of Nepeta cataria Linne (Nat. Ord. Labiatic). This oil has a mint- and camphor-like, but not particularly agree- able odor. Specific gi-avit}^ L04L It has not yet been chemically examined. Oil of Cedar Leaves, Ainericaii. {Gcrtnan : Cedornblatter-Oel.) Distilled from the leaves of the Red Cedar, Juniperus Viryiiiiana Linne (Nat. Ord. Coniferce). A colorless liquid, having a savine-like odor. Specific gravity about 0.884. Optical rotation — 8^ 15'. The above characters are based upon the examination of a com- mercial oil, but an oil distilled in our Garfield factory, from leaves collected in late autumn, differs considerably, especially with regard to its rotation. It is a pale greenish-yellow liquid, having a i^ersistent, but not disagreeable odor. Specific gravity 0.880. Optical rotation -j-59° 5'. It has not yet l)ee:i chemically examined. The medicinal properties of the oil are prol)ably similar to those of the official Oil of Savine. 48 NON-OFFICIAL ESSENTIAL OILS. Oil of Cedar ^Vood, Florida. (German : Cedernholz-Oel.) Distilled from the wood of Juniperus Virginiana Linne (Nat. Ord. Coniferoi). A pale yellow or greenish-yellow, thickish licjuid, having a char- acteristic, agreeable odor. Specific gravity 0.940 to 0.960. Optical rotation — 20" to — 40\ Refractive index "jj 1.50507 at IT C. It con- tains cadinene CisH^j, and cedar camphor CioH-eO. The oil is used largely for perfuming ordinary soap. Oil of Cedar Wood, for microscopical p>nr poses, has the refractive index n^ 1.51683 at 17° C. Oil of Cedar Wood, Lebanon. (German: Cedernholz-Oel, Libsiiion.) Distilled from the wood of Cedriis Libani Barr (Nat. Ord. Coni- ferce). The oil has a brownish-yellow color, and a very agreeable, cedar- like odor. Specific gravity 0.985. Optical rotation — 10° 48'. Messrs. Schimmel & Co. have also distilled the following oils from woods of uncertain botanical origin. (See Bericht, April, 1892, p. 41): Oil of Cedar Wood, Corinto. The oil has a yellow color. Specific gravity 0.906. Optical rota- tion 17° 23'. Oil of Cedar Wood, Cuba. The oil has a slightly yellowish color. Specific gravity 0.923. Optical rotation -|-18 6'. It contains cadinene CisH-ji. Oil of Cedar Wood, La Plata. The oil has a light blue color. Sjjecific gravity 0.928. Ojrtically inactive. Oil of Cedar Wood, Punta Arenas. The oil has a light blue color. Specific gravity 0.915. Optical rotation — 5° 53'. It consists chief!}- of cadinene C15H24. Oil of Celery. (flrrman : Sellerie-Oel.) Distilled from the fruit of Apiiim graveolens Linne (Nat. Ord. UvibelUfcra'). NON-OFFICIAL ESSENTIAL OILS. 49 Tile oil lias a yfllowish color, and the characteristic odor aud taste of celery. Specific gravity 0.880 to 0.890. Optical rotation -|-67' 4'. It contains dexti'ogyrate linionene, but no pinene. An adulteration with oil of turpentine may thus readily be detected. Oil of Chamomile, German. (German: Chamillon-Oel, Deutsch.) Distilled from the flower heads of Motrin aid ChdtuotuUht Linne (Nat. Ord. ComposiUe). The oil has at first a bluisli color, which, by exposure to light, changes to green and l)rown. It has the characteristic odor of cham- omile, and a bitterish, aromatic taste. Specific gravity 0.930 to 0.945. At a low temperature the oil solidifies to a butter-like mass, which is due to the i)resence of a paratifin like body, having in a pure state a melting point of 53" — 54' C. The oil appears to contain esters, but it has not yet been sufficiently examined (see Ber. d. deutsdi. cheni. Ges., 4, p. 36: also Schimmel & Go's Bcricht, April, 1894, p. 13). Oil of Chamomile, Roman. (German: Chamillcn-Ocl, Kiiioisch.) Distilled from the flower heads of Aiifliriiiis iioJulis Linne (Nat. Ord. Co)it2)osit(:e). The oil has at first a bluish color, which changes to greenish- yellow or brownish yellow. It has a strong, agreeable odor, and burning taste. Specific gravity 0.905 to 0.915. It contains the iso- butyl esters of isobutyric and angelic acids, the amyl esters of tiglic and angelic acids, the hexyl esters of tiglic and angelic acids, aud anthemol C,„H,r, O. (See Liebig's Annaleii, Bd. 195, 1879, p. 78.) Oil of Champaca. (German : <_'haiuiiac"i-(.)fl.) Distilled in Java from the flowers of Michdia Chainpaca Linne A thin, pale yellcnv liquid, having an odor reminding somewhat of oil of orris. Specific gravity 0.914. Optical rotation — 13 14'. x\n oil received some years ago from Manila, which had been distilled from freshly gathered Champaca flowers, was of quite a different character from the above described Java oil. It had a reddish-yellow color, and an incomparable fragrance, somewjiat re- minding of cassie flowers. Even at ordinary temperatures an abund- ance of crystals separated from this oil. (See Schimmel & Co.'s Beridd, April, 1894, p. 58.) The flowers of Midielia longifolia, which have likewise been dis- tilled in Java, afford a nearly colorless essential oil. This is very volatile, and has an odor strongly reminding of basilicum. Ite 50 XOX OFFICIAI. ESSENTIAL (IILS. sp.rilic gravity is O.ss;;. Optiral rotation —12 50'. {Bevk-lit, April, l«!t4. p. 59.) Oil of Cliekeii Leaves. (Gcriiiun : Clickeiililiiin'r-Ool.) Distilled from the leaves of Mjirtiiji Clicken (Nat. Ord. Mijrtacere). The oil has a yellowish or greenish color, and an agreeable, aro- matic odor. Specific gravity 0.879. Optically dextrogyrate. It con- sists chiefly of 2)inene, with some cineol, and an undetermined higher boiling ('220 to 280 C.) portion. Oil of Cherry Laurel. {(jcriiKOi : Kirschlorl)for-()el.) Distilled from the leaves of Pnams L<(>n-()-cfV(isiis Linue (Nat. Ord. Rosacea'). Specific gravity l.O."),") to l.Ofi."). It contains bt nzaldehyde, hydro- cyanic acid (al)out o i)er cent.) and benzyl alcohol. It is therefore similar in com]iosition to bitter almond oil. It is used chiefly in the preparation of liquors. Oil of Cistus. [Geriiutii : Cistus-Oel.) Distilled in southern Spain from the leaves of Cisfus ladaniferns Dinne (Nat. Ord. Cistaceir}. The oil has a (lisagreeal)le, nai-cotic odor. Sjieciflc gravity 0.925. It boils between 105 and 280' C, l)ut has not yet been chemically <'.\'amined. Oil of Citroiiella. (German : CitronoU-Oel.) Distilled in India from the grass of species of Aii()ro]>0(i(y)i, tisually referred to ^4. Aanliis Linne (Nat. Ord. Gndiiriied'). A limpid, yellowish t)r greenish-yellow, or, when rectified, nearly colorless liquid, having a very agreeable odor. Specific gravity 0.895 to 0.910. The chemical invetitigations of this oil present somewhat varying results, which may no doubt be explained in ])art by the supposition that the oil is not of constant conq)ositiou, and not always the product of a single plant species. E. Kremers {Proc. Amer. Pharm. Assoc, 1887, pp. 563-578) found the oil to contain a terpene, heptoic aldehyde CtHhO, fractions boiling at 217-2:2, and 222-230" C. respectively, and having the conq)i)sition Ci„HimO, which were designated as citroHcIIol, and acetic and valerianic acids in the form of esters (.see also Kremers, Ainei: Chrm. Jonni , XIV, pp. 2();5-212; Dodge, Utidem., XI, p. 456, XII, p. 558; Semmler, Ber. d. deutsch. chem. Ges., 24, p. 208, 26, p. 2254). NON-OFFICIAL ESSENTIAL OILS. 51 Messrs. Schiiuinel & Co. {Bericht, October, 1888, p. 16, October, 1893, p. 11, April, 1894, p. \~i) have fouud iu tliis oil: camphene, dipentene, geraniol CulHl^O, citronellal d,, Hi„0 (see the latter, under Chemical Prepara,tions, Part III), aud from 1 to 3 per cent, of lajvogyrate borneol doHi^O. Oil of Citronella has heretofore been largely adulterated, even iu India, and especially with fatty oils aud petroleum. These may be detected by the following simple and reliable test, proposed by Messrs. Schiunuel & Co. : If 1 Cc. of the oil be vigorously shaken in a glass- sto2)pered cylinder or well corked test tube with 10 Cc. of alcohol, of 80 per cent, by volume, it should form a clear or only slightly opal- escent solution, from which on standing for at least twelve hours no oil dro]« should separate, either on the surface or at the bottom of the liquid. Oil of Citronella is used chiefly for its agreeable perfume, in soaps, etc. Oil of Citronella Fruit. (Gtiniaii : ('itroiK'Hfriicliti'-f )fl.) Distilled from the fruit of Tetraidherii cifnifa Nees (Nat. Ord. Lauraceie). This oil has an agreeable, verbena-like odor, and has therefore been designated Oil of Vcrhemt. Java. Specihc gravity 0.894. It ct)n- tains citral and a ter})ene. Oil of Clove Root. (German : Nelkfii\vurz-Of 1.) Distilled from the root of Geinii iirhainnii, Linne (Nat. Ord. Ronacece). The oil has an exceedingly agreeable, cinnamon-like odor, aud a spicy taste. It has nt)t yet been further examined. Oil of Cochlearia, Synthetic. [German: Luttelkraut-Ool, Synthetisch.) This is identical with the chief constituent of the oil of scurvy- grass {Cochlearia officinalis Linne, Nat. Ord. Cracifera'). It ii the isosulphocyanate of secondary butyl alcohol, or secondary' butyl thio- carbimide, CSN— CH (C^ H.,)CH:,. Its specific gravity is 0.944 at 12' C. and boiling point 159" to 160" C. A good S^nritus Coehlearice may be made by dissolving 2 grammes of the oil in 1 kilo of 70 per cent, (by volume) alcohol. It may be noted that in commerce a mixture consisting simply of the oil of nuistard aud oil of rue is frequently sold as Oil of Cochlearia, but which has not the properties of the true oil. 9 52 NON-OFFICIAL ESSENTIAL OILS. .Oil of Coiiiiac, Artificial, see Ether, Oenautliic, under Chemieal Preparations, Part III. Oil of Costus. {(xerinan : Costus-Oel.) Distilled from the root of Costiis sjjcciosas (Nat. Onl. Zinr/iberacece). The oil lias a jiale yellow color, and an odor reminding at first of elecampane, but whieli after some hours becomes violet-like. Specific gravity 0.982. Optical rotati(jn -flo' 29'. It begins to b(jil at 27.') C., and at a somewhat higlier temperature complete decomposition ensues. It lias not yet been more tlioroughly extimined, but appears to have only scientific interest. Oil of Coto Bark, Para. {German : Paracotoriiuk-n-Oel.) The botanical origin of this bark is unknown. Tlie oil is color- less, and has an agreeable odor. That distilled by Messrs. Schimmel & Co. has a specific gravity of 1.018, and optical rotation -\-~y 40'. It is soluble in three times its volume of 70 per cent, alcohol. The oil contains chiefly cadinene Ci.=,Hj4, and methyl-eugenol. (See Liebig's AiiHdh'ii. 271, p. 800, and Ber. d. deutsch. cliem. Ges., 26, p. 2794.) Oil of Cumin. {German: Ciimin-Oel or Romisch-kiimmcl Ool.) Distilled from the fruit of Cumiimni Cymmnni Linne (Nat. Ord. Uinbellifera'). The oil is a colorless or yellowish, limpid liquid, having the characteristic odor of cumin, and a sharp, spicy taste. Specific grav- ity 0.890 to 0.980. It contains cyiiiol CjoHu, and cumin alde- liyde C,„H,,0. Oil of Curcuma. (Gfrinan : Curcuma-Oel.) Distilled from the rhizome of Ciirciuna Tonga Linne (Nat. Ord. Zingiberacece). The oil is limpid, has a lemon-yellow color, a penetrating odor, and a burning taste. Specific gravity 0.942. It contains i)liellandrene, and apparently a body isomeric with carvol (',„H,, O. It has found as yet but little practical use. Oil of Cuscus, see Oil of Yetiver. NON OFFICIAL ESSENTIAL OILS. o:5 Oil of Dam i mm. (GiTmaii : Damiana-Oel.) Distilled from the leaves of Tnrnera microphylht D. C. (Nat. Ord. Turneracece). The oil is a greenish, thick, viscid liquid, having a chanioniile-like odor. Specific gravity 0.986. It boils between 250" and 310"' C, and contains in the higher boiling portion a blue oil. Its composition and l)roperties have not been further determined. Oil of Daucus, see Oil of Carrot, Wild. Oil of Dilem Leaves. (German: Dilem-Oel.) The botanical origin of these leaves, obtained from Java, is un- known. Tlie oil is quite thick, has a yellowish-green color, and an- odor reminding of patchouli, but finer and fresher than the latter. Specific gravity 0.962. It boils between 250 and 300" C. Oil of Dill. {(icrinnn : Dill-Oel ) Distilled from the fruit of Anethiini graveolens Linne (Nat. Ord. U)ii.1)eIIiferce). The oil has a pale yellow color, a characteristic, penetrating odor, and at first a sweetish, afterwards sharp and burning taste. Specific gravity 0.905 to 0.915. Optical rotation +70' to -fSO . It contains limonene and carvol. The oil from East Indian Dill has an odor quite different from German Dill Oil. Its specific gravity is 0.970. Optical rotation -|-41 30'. In distinction from the preceding it con- tains a body which is heavier than water. (See Schimmel & Co. 's Bericht, October, 1891, p. 12.) Oil of Dittany. ((iirnum : Bittany-Oel or Cunila-Oel.) Distilled from the herb of Cniiihi Mariana, Linne (Nat. Ord. Labiat(T). It has a reddish-yellow color, and a thyme-like odor. Si)ecific gravity 0.915. It contains a considerable amount of a phenol, probably thymol, but has not yet been fvirther examined. Oil of Elecampane. (Gcvma)i : Alant-Ool.) Distilled froni tlie root of Inula Helenium Linne (Nat. Ord. Co7n- positce). 54 NON-OFFICIAL ESSENTIAL OILS. It is solid at onlinarv temperatures, and c(jnsists cliieflj' of alanto- lactone (helenin) ('u II.j„(^() , witli a little sesfiiiiterpene. Oil of Elemi. (OtriiKiu : Eleiui-Oel.) Distilled from ^lanila Elemi, an oleo-resin of uncertain botanical origin. The oil is nearly colorless, and lias an agreeably ai'oniatic odor and taste. Specific gravity 0.87 to 0.90. It contains phellan- drene and dipentene, and higher boiling bodies which probably con- sist of polyterpenes and oxygenated compounds. It is used chiefly for its agreeable perfume. Oil of Estrai^oii. {German : Estraji'oii-Oel.) Distilled from the herb of Artemisia Dracnnculn-s Linue (Nat. Onl. Compositce). The oil has a peculiar odor, and a mildly aromatic taste. That distilled by Messrs. Schimmel & Co., which is of exceptionally line quality, has a specific gravity varj'ing from 0.906 to 0.932, and an optical rotation of -|-5" 15' to -j-S^ 10', while some commercial oils vary in specific gravity from 0.920 to 0.9fi0, with an optical rotation of +2^ 32' to +2^ W'. The oil contains i)ara-methoxy-allyl-benzol C^Hi (0CH3)CHi — CH=CH2, which is isomeric with anethol, and can be converted into the latter by heating with an alcoholic solution of i^otassium hy- droxide. This body is luidoubtedly also identical with the so-called "Estragol." (See Compt. rend., 117, p. 1189, Ber. d. deufsch. chem. Ges., 22, p. 2743, and Schimmel & Co.'s Berichf, April, 1894, p. 28.) Compare also Oil of Anise Bark. Oil of (7}jilaii;;al. {(hrmaii : Galyant-Oel.) Distilled from the rhizome of AJpiaia offlcinarion Hance (Nat. Ord. Scitauiine(t'). A reddish yellow liquid, having an aromatic, cajuput-like odor, and a strongly camphoraceous taste. Specific gravity 0,921. Sligl\tly la;vogyrate. It contains a considerable amount of cineol. and is used to a slight extent medicinally. Oil of (lalbaniiin. {(lirmttn : Galb:uium-()fl.) Distilled from Galbanum, a gum-resin obtained from Fenda gcdhaviflua) Boissier et Eidise (Nat. Ord. VmheUiferce). t NON-OFFICIAL ESSENTIAL OILS. 55 The oil lias a light yello%v color, aud the characteristic odor of the drug. Specific graAity <).!»10 to U.9o(). It boils between 165' and 300^ ('. It contains cadinene CinHj4- Oil of Garlic. (Gcrmitn : Kiioblavich-Oel.) Distilled from the bnlb and herb of Allium, saflvitiii Linne (Nat. Ord. Liliacca'). Tlie oil has a yellowish color, and a characteristic, exceedingly })enetrating odor. Specific gravity 1.053. It contains the coniponml Cn HijSo, which is i)robably allyl-propyl disulphide ( " "i \, and C HiuSj, wl^ich is probably diallyldisulphide I \ \)- The higher boiling portions contain bodies of the composition C,;Hi„S:i and CvHioSi (see Arcliio der PJiann., 1893, p. 434, and Schimmel & Co.'s BericJd, April, 1893, p. 34). The oil is a powerful irritant and vesicant, but has been nsed in minute quantities for imparting flavor to pickles and sauces. One part of the oil represents the strength of about 1600 parts of garlic-. Oil of Oeraiiiniu or Rose Geranium. {GcrnuiH : Geranium-( )el. ) Distilled from the herb of several species of Pelargonium, especially P. Radula Aiton, P. capitutuhi Alton, and P. (xJorafis.^imum Linne (Nat. Ord. Geraniacece). The following varieties of this oil are distinguished in commerce : Algerian. Specific gravity 0.890 to 0.898. Optical rotation — 7 to — 9 French. " " 0.894 to 0.899. " " _9 to — 13 Reunion. " " 0.886 to 0.895. " " _8 to— 11 Sjxinish. " " about 0.898. " " about — 8 An oil distilled by Messrs. Schimmel & Co. , from plants cultivated in Leipsic, had a specific gravity of 0.906, and an optical rotation of —16°. The above oils have a pale yellowish or greenish (Reunion) color, and an exceedingly agreeable, rose-like odor, which render tliem valuable in perfumery. The chief constituent of the oils is geraniol, C10H17-OH (see the latter, under Chemical Preparations, Part III), which is present in amounts of about 80 to 85 per cent. The geraniol is contained in the oils in the form of esters, among which that of tiglic acid predominates (see Schimmel & Co.'s Berichf, April, 1894, p. 31). An excellent test for the purity of the Geranium Oils, and wliicli may serve to detect adulterations with fatty oils, petroleum, oil cf ofi NON-OFFICIAL ESSENTIAL OILS. turpentine, etc. , is their property of f onning a perfectly clear solution witli two or three times tlieir volume of 70 per ceut. alcoliol. Oil of Geniiiiuni, East Indian. fGcnnaii: Geraiiiuui-Oel, liidi?clif.s.) This is the so-called Turkisli Geraniion or Pnintdrosd Oil. It is distilled iu tlie northern jn-ovinces of India from the grass of a species of Andropogoit (regarded as ^4. SclicentDifluis Linne). Nat. Ord. Graminefe. A nearly colorless, or pale yellowisli liijuid. Specitic- gravity 0.890 to 0.900. Opticall}- inactive or slightly la?vogyrate (0 to about — 2 ). It consists chiefly of geraniol or its esters, and, like the preceding oils of geranium, is soluble in two or three times its volume of 70 jier cent, alcohol. The oil is valued chiefly for its agreeable perfume. Oil of Ginger. (Gcrntaii : Ing-wer-Ocl.) Distilled from the rhizome of Zingiber officinale Roscoe (Nat. Ord. Scitanmiece). The oil has a pale yellowish color, the characteristic odor of ginger, and an aromatic, somewhat burning taste. Specific gravity 0.880 to 0.885. Optical rotation —2o to — 40 . Its chemical constituents have not yet been suflficiently investigated, but IMessrs. Schimmel & Co. (Bericht, October, 1S98, p. 22, and April. 1894. p. 33) have shown it to contain canipliene and pheJJandrene. It is used chiefly in the ]ireparation of liquors. Oil of (linger Grass. ((itriuan : Ging'orgrass-Oel.) This appears to l)e derived from the same botanical source as the East Indian or so-called Turkisli Geranium Oil (see above). It is however, a less valuable i>roduct, and is often grossly adulterated, especially with fatty oils (see Schimmel & Co. 's Bericht, April. 1804, p. 31). Oil of Golden Rod. (Germnn : GoldnitluTi-Oel.) Distilled from the herb of Soliclago oclora Alton (Nat. Ord. Coiii. jMsitce). This is the oil of the so-called "sweet-scented golden rod." It has a pale greenish-yellow color, and a strongly aromatic odor. Specific /gravity 0.963. It appears not to have been further examined. NON-OFFICIAL ESSENTIAL OILS. o? No less than 40 distinct species of Solidago, or " Gokleu Rod," occui' in North America, east of the Rocky Mountains. In addition to the above mentioned species, we have distilled the flowering herb of Solidago Canadensis Linne. This yields a i)ale yellowish-green oil, having an agreeably aromatic odor. Specific gravity O.SoD. Oi)tical rotation — 11 10'. A partial examination of the oil, made in our Garfield laboratories, has shown it to consist chiefly of terpenes, among which pinene and phellandrene have thus far been identified. Oil of Ground Ivy. (Gcnnan : Guiidennaniikraut-Oel.) Distilled from the dried herlj of Glechoma hederacea Linne (Nat Ord. Labiatce). The oil has a dark green color, and an odor which is difficult to define, but by no means agreeable. Specific gravity 0.925. Oil of Guaiacum Wood. {Ginnnn: Guaiacholz-Oel.) Distilled from the wood of an undetermined species of Guaiacum from South America, where it is known as "Balsam Wood" (Palo halsamo). The oil is excejitionally thick and viscid, has an exceedingly agreeable violet- and tea-like odor, and at ordinary temperatures assumes a crystalline character. The crystalline l)ody is of alcoliolic nature, melts at 91 C, and appears to have the composition Ci4Ho40 or C,.,H.,«0. The oil is ^■aluable as a perfume, and is used in both floral extracts and soaps. An oil recently brought into connnerce under the fanciful name of " Champaca Oil" or " Champaca-wood Oil" has not the slightest similarity with true Champaca Oil (see the latter) from the flowers of MicheUa Champaca Linne (Nat. Ord. MagnoUocea'), ])ut is perfectly identical with tiie above descril)ed Guaiacum Wood Oil. The so-called "Champacol" is also nothing more than the above described crj'stal- line alcohol. (.See Schimmel & Co.'s BericJit, April, 1S92, p. 42, and April, 1893, p. 32.) Oil of Hedychiuiii. {German : Hed5'chium-Oel.) Distilled in Java from the flowers of Hedijcliium Coronarium Linne. It has an exceedingly pleasant, but very mild odor. Specific gravity 0.869. Optical rotation —0" 28'. 58 NON-OFFICIAL ESSENTIAL OILS. Oil of Helifhr.vsum. (Gennan : Hflichrysuiii-Oel.) Distilled from the fio\verin<;- lierh of HcIicltrf/sKiii Stiechas (Nat. Orel. Coinponitce). It has an odor reiuiudiug of oils from the Couifera'. Specific gravity 0.873. It boils chiefly between 155 and 170 ('., and prob- ably contains considerable pinene. Oil of Hemlock. (German : Hemloc;ktanncii-( )el.) Distilled from the leaves and twigs of Tsuga canadensis Carr. (Abies Canadensis Michx.). Nat. Ord. ('oniferce. A colorless liquid, of agreealile odor, much resembling the 0/7 ()/■ Sjjruce, and probably similar to the latter in composition. Specific gravit}^ about 0.913. Optical rotation — 23' 55'. This oil appears to be frequently confused widi the true Oil of Spruce from the fact that the tree affording it is sometimes known as "Hemlock Spruce." It appears not to have been chemically examined. The true Oil of Spruce (see the latter) is obtained from a different botanical source. Oil of Heracleiim. (Gcnnnii : IIcraeleiim-()el.) Distilled from the fruit of Heracleum Sphondi/linm Linne (Nat. Ord. Umbellifene). The oil has a pale yellow color, and an acid reaction. Specific gravity 0.80 to 0.87. It boils between 80' and 300 C, and contains a number of esters. The following compounds are stated to be con- tained in the oil: ethyl and but^d acetates, ethyl and hexyl alcohols, and octyl capronate. (See Liebig's Annalen, 153, 1869, p. 1; 185, 1877, I.. 26; and Ber. d. deutsch. cheni. Ges., 9, 1876, p. 998.) Oil of Hops. {Gennnu : Ildplcn-Oel.) Di.stilled from tlie strobiles of Hidnuliis Liipulus Linne (Nat Ord. Urticace(e). The oil has a greenish color, and a strong, penetrating odor of hops. Specific gravity 0.855 to 0.880. Its constituents have not yet been sufficiently examined. It has been used for imparting aroma to beer. Oil of Horseiiiint. (German : Monarden-Oel.) Distilled from the herb of Monarda punetata Linne (Nat. Ord. L(d>ia1(r). NON-OFFICIx\L ESSENTIAL OILS. 59 The oil has a yellowish-red or brownish-red color, and a strong, thyme-like odor. Specitic gravity 0.'J30 to 0.936. It contains thymol a terpene, and apparently the formic, acetic and butyric esters of an alcohol of the composition do His O. (See Amer. Juiirn. Pharia., 18H8, p. 120.) It is used chiefly in liniments. Oil of Hyssop. (dcnnan : Ls()p-(.)el ) Distilled from the herb of Hyssoptis offlcinalifi Linne (Nat. Ord. L(tbiat(c). Specific gravity about 0.932. It appears not to have been chemically examined. It is used medicinally, ami in the preparation of liquoi'S. Oil of Iiiiperatoria, see Oil of Masterwort. Oil of Iva. {Oerman: Iva-Oel.) Distilled from the flowering herb of Acldllea moschafa Wulfen (Nat. Ord. Compositce). A very aromatic oil, of a bluish-green color. Specific gravity about 0.934. It is used in the preparation of the Swiss Iva liquor. Oil of Jaboraiidi. (ircriiMa: Jiibonindi-Oel.) Distilled from the leaves of Pilocarpu.-i i^anatifolmx Lemaire (Nat. Ord. Ri(tacece). The oil has a bright yellow color, a penetrating odor, and a mild taste. Specific gravity 0.875. It boils between 180 and 290 C. The portion distilling above 260 C. solidifies in the cold, and contains a solid paraffin-like substance which melts at 27 to 28 C. No use appears to have yet been made of this oil. Oil of Ktempfeiia. (German : Kiempferia-C )el. ) Distilled in Java from the rhizome of K. 22, and Liebig's Annalen, Bd. 258, p. 340.) It is recommended as a perfume for soaps, etc. Oil of Masterwort. (German : Meisterwiirz-Oel.) Distilled from the root of Imppratoria OstriithiuDi Linne (Nat. Ord. UiiibeUiferce). The oil has a stronglj- aromatic odor, reminding of Angelica, and a biting, ai"omatic taste. Specific gravity 0.877. It boils between 170 and 190° C, and appears to consist chiefly of hydrocarbons, which liave not been further exainined. Oil of Mastic. (German: Mastix-Oel.) Distilled from Mastic, a resinous exudation from Pisfaeid Leiitiscim Linne (Nat. Ord. Aiiacardiacea'). The oil has a yellow color, and a characteristic, strongly Ijalsamic odor of the drug. Specific gravity 0.858. Optical rotation +25 . It appears to consist chiefly of terpenes. Oil of Matico. (German : Matic'o-Oel.) Distilled from the leaves (and the flowers) of Piper an fpi>tii folium R. et P. (Nat. Ord. Pipcracea). The oil has a yellowisli-brown c-olor. and a i;eculiar odor. The specific gravity of the oil from the leaves i.s 0.93, wliile that from the flowers is 1.13. The 1)est known constituent of tiie oil is the so-called matico camphor C 12 Ho oO. (See .B('r. d. deutsdi. chcm. Ges., 16, 1883, p. 2841.) Oil of Melissa. {German: Melissen-Oel.) The ti'ue Oil of Melissa, from Melisaa officinalis Linne (Nat. Ord. Labiata;), commonly known as Balm, is not an article of commerce. The article known vmder this name, or as Oleitni Melissa' eitratinn, is obtained bv distilling the leaves of the melissa with lemon oil. 04 NON-OFFICIAL ESSENTIAL OILS. Oil of Melissa, East Indian, se( (Ml of Lrnionijrass. (Ml of 31('w. {German: ]{aiTWurz-Oel.) j Distilled from tlie root of Meiun (itlimiKuiiiciim Jac(i. (Nat. Ord. UrahelUfertii). The oil has a dark yellow color, and an odor reminding of lovage. Specific gravity 0.999 at 21° C. It boils between 170" and 300' C, yielding finally a greenish-blue fraction. It easily becomes resinified on boiling, but appears not to have been chemically examined. Oil of 3Iii;rnonette, see Oil of Keseda. Oil of Milfoil. (Gerruaa : Schafgarben-Oel.) Distilled from the fresh flowering herb of Achillea MUlefolium Linne (Nat. Ord. Compositce), known also as Yarrow. The oil has a yellowish, green, or bluish color, a penetrating odor, and an aromatic, camphor-like taste. Specific gravity 0.910 to 0.920. It appears not to have been chemically examined. It is used to a small extent medicinally. Oil of 3Iint, Mountain, see Oil of Mountain Mint. Oil of Mint, Water, s(e Oil of AVater 3Iint. (Ml of Mint, Wild, see Oil of Wild Mint. Oil of Monarda, see Oil of Horseniint. Oil (»f 3Iosoi Flowers, see Oil of Cananga. Oil of Mountain Mint. (Gcnitan : Pycnanthemum-Oel.) Distilled from the dried herb of Pycnaiifheinnni incanum Michaux (Nat. Ord. LahiaUe). The oil has a reddisii yellow color, and a strongly aromatic* odor. Specific gravity O.Oo."). It is soluble in twice its volume of 70 per cent, alcohol, but has not yet been chemically examined. Oil of Mugwort, see Oil of Artemisia vuliraris. Oil of Musk Root, see Oil of Sunibul. Oil of Musk Seed, see Oil of Anibrette Seed. NON-OFFICIAL ESSENTIAL OILS. 65 Oil of Myrrh. {German: Myrrhen-Oel.) Distilled from Jlyrrh, a giini-resin obtained from Commiphora Mijrrha (Nees) Engler (Nat. Ord. Burseraceie). The oil is a yellowish, rather viscid liquid, having a strong odor of the drug. Specific gravity 0.990 to 1.010. Optical rotation —60" 2. It distills chiefl}^ between 270° and 290' C, but its constituents have not been more exactly identified (see Pharmacographia, 2 Edit., p. 144). Oil of Myrtle, Spanish. (German: Myrten-Oel.i Distilled from the leaves of llijrfus coviniunU Linne (Nat. Ord. Myrtacece). The oil has a light yellow color, and an agreeably aromatic odor. Specific gravity 0.89 to 0.92. Optically dextrogyrate. It contains cineol, dextrogyrate pinene, and dipentene (see Archiv der Pharm., Bd. 227, p. 174). It has been used medicinally as an antiseptic, in diseases of the respiratory organs and the bladder, and as a local appli- cation in rheumatic affections. See also Myriol, under Chemical Preparations, Part III. Oil of Xiobe, see 3Iethyl Benzoate, under Chemical Preparations, Part III. Oil of Olibaiiiiiu. (Gcniian: Olibauum-Oel or AVeihrauch-Oel.> Distilled from Olibanum, a gum-resiu obtained from species of Boswellia (Nat. Ord. Burseraceu'). A colorless liquid, having an agreeable, balsamic odor. Specific gravity 0.87.'> to 0.885. Optical rotation — 11 ' 35'. It consists chiefly of laevogyrate pinene, with some phellaudrene, dipentene, and oxy- genated bodies (see Liebig's Annulen, 252, 1889, p. 94). The oil is considered of value in mixtures of soap perfumes, and as a con- stituent of fumigating tinctures. Oil of Onion. (German: Zwiebel-Oel.) Distilled from the fresh herb and bulb of the common onion Allium Cepa Linne (Nat. Ord. Liliacea). The oil has a reddish-brown color. Specific gravity 1.040. Optical rotation — 5\ It contains the compound CsHiaSa, and appears to resemble in its general characters and composition the Oil of Garlic, see the latter. «'j XOX-OFFICIAL ESSENTIAL OILS. Oil of Opoponax. (German : Opoponax-Ocl.) Distilled from Opoponax, a gum-resin obtained from Opopona.v Chironium Koch (Nat. Oi'd. Umbelliferce). The oil has a greenish-yellow color, and an agreeable, balsamic odor. It resinifies (jiiickly on exposure to the air. Specific gravity 0.860 to 0.910. It boils between 200 and 300' C, the lower boiling portions representing tlie characteristic odor of the oil, but has not yet been chemically examined. It appears to be of value in jier- fumery. Oil of Origaiiiim, Cretian {Oleum Origani Cretici). (German: Spanisch Hopfen-Oel.) Distilled from the herb of several species or Tarieties of Origanum gi'own in the Orient, such as O. creticum Linne, O. megastachyum , Lk., O. macrostacJtyiun Lk., and O. Jnrtuni Lk. (Nat. Ord. Labi(ttte). The oil when freshly rectified has a golden- yellow color, but on keeping, or on exposure to the air, gi-adualh' accjuires a reddisli or reddish-brown color. It has a penetrating, aromatic, thyme-like odor. Specific gi'avity 0.960 to 0.980. Its chief constituent is carvacrol, of which it sometimes contains as much as 80 per cent., and a good oil .should not contain less than 50 per cent, of this body. (See Carvacrol, under Chemical Preparations, Part III.) The above oil, when pure, is not colorless, and, in order to retain it of a light yellow color for microscopical purposes, it should be kept in a dark place, and in well- stoppered bottles, which should be as completely filled as possible. Oil of Origaniim, French, see Oil of Marjoram, Wild. Oil of Orris. (German: Iris-Oel or Veilchenwui'zel-Oel.) Distilled from the rhizomes of the following species of Iris: /. germaxica Linne, I. palUda Lam., and I. florentina Linne (Nat. Ord. Tridacece). Tills oil is solid at ordinary temperatures. It consists of myristic acid CuHj-Oj, associated with a relatively small amount of liquid substance to which its ex(|uisite and persistent fragrance is due. The constituent of orris root, or of the essential oil of orris, which possesses the characteristic, violet-like odor has recently been isolated by Tiemanu and Kriiger (see Ber. d. deiitsch. chem. Ges., 26, 1893, pp. 2675-2708). This body, which has been termed irone, is a ketone of the composition CaHooO. It distills at 144' C, under a pressure NON-OFFICIAL ESSENTIAL OILS. G7 of 14 Mm., has a specific gravity of 0.939 at 20' C, aud is dextro rotatory. By the elimination of the elements of water it is converted into a hydrocarbon termed irene CiaHis. Tlie oil of orris distilled by Messrs. Schimmel & Co. has been found to contain from 10 to 15 per cent, of iroue. A body liaving the same empirical composition as irone, and structurally isomeric with it, has also been obtained by the above men- tioned chemists by syntlietic means, and is termed ionone. This is prepared by the condensation of citral and acetone, whereby tlie so-called pseudo-ionone is first ol)tained, and the latter, by treatment with dilute sulphuric acid, suffers a molecular change, becoming converted into the isomeric ionone. Ionone, Cm HooO, distills between 126° and 128° C. under a pressure of 12 Mm., has a specific gravity of 0.9351 at 20 C, and is optically inactive. By the elimination of the elements of water it is converted into a hydrocarbon termed ionene, Ci3Hie. Ionone possesses in a remarkable degree of purity and concentration the characteristic, fragrant odor of fresh violets. This odor is t)nly fully developed when the substance is in a diluted state, and ionone is therefore brought into commerce in the form of a ten per cent, alcoholic solution. It is thus adapted for use in floral extracts, toilet soaps, aud other perfumed articles. Oil of Palmarosa, see Oil of Geranium, East Indian. Oil of Para Coto Bark, sec Oil of Coto Bark, Para. Oil of Parsley. {Gci-maii : Petersilien-Oel.) Distilled from the fruit of PetroscUn nm sativum Hoffm. (Nat. Ord. Umbelliferce). A colorless or pale greenish-yellow liquid, liaving a strong odor of parslej'. Specific gravity 1.07. It contains la^vogyrate pinene and apiolCi2Hu04 (see the latter, under Chemical Preparations, Part III). The oil is used occasionally as a diuretic. Oil of Parsley Root has also been distilled by Messrs. Schimmel & Co. The yield is very small, amounting to but 0.08 per cent, of the dry root. The oil has a specific gravity of 1.049. At ordinary temperatures it separates crystals, which probably consist of apiol. Oil of Parsnip. (German : Pastinac-Ool.) Distilled from the fruit of Pastinaca sativa Linne (Nat. Ord. Umbelliferce). 68 XOX-OFFICIAL ESSENTIAL OILS. Tlie oil lias a yellowish color, and a characteristic, agreeable odor. Specific gravity 0.870 to 0.890. It contains the octyl esters of pro- pionic and butyric acids. Oil of Patchouly. (German: Patchouli-Oel.) Distilled from the leaves of Pogo.stemon Patclioidi Pellet. (Nat. Ord. Lahiatce). A yellowish -green or brown, somewhat thick liquid, having a penetrating and exceedingly persistent odor. Specific gi-avity 0.97 to 0.99. It contains cadinene C15H24, and patchouly alcohol, or so-called "patchouly camphor" Ci5H-„0 (see Liebig's Annaleii, 150, 1869, p. 374; 238, 1887, p. 81; Covij^t. rend., 84, 1877, p. 88). An oil distilled in Java from a species of Pogostemon closely related to the above has a yellowish color and an odor reminding of patchouly, but agreeably modified by the presence of a sul)Stance having an odor resembling anise-aldehj'de. The specific gravity of this oil is O.Ofil. Optical rotation — 32 17'. It is said, under some circumstances, to deposit a stearopten (see Schimniel & Co.'s Bericht, April, 1894, p. 58). Oil of Pear, see Amyl Acetate, under Chemical Preparations, Part III. Oil of Peimyroyal, European, see under Oil of Hedeonia, Part I. Oil of Pepper. {German: Pfeffer-Oel.) Distilled from Black Pepper, the fruit of Piper nigrum Linne (Nat. Ord. Piperacece). A yellowish, limpid liquid, having a stronglj' pungent, pepper-like odor and taste. Specific gravity 0.880 to 0.905. It contains phellan- drene Cm Hip, and cadinene C15H04 (see Archiv der Pharm., 1887, p. 515, and Schimmel & Co.'s Bericlit, October, 1890, p. 39). Long Pepper, the fruit of Piper longuni Linne, yields a thickish oil, of a light gi'een color, and an odor reminding moi'e of ginger. Specific gravity 0.861. It boils between 250' and 300' C. Oil of Pepper, Japanese. {German: Pi'effer-Oel, .lapanisches.) Distilled from the iruit of Xanthoxyhnu piperitvm DC. (.Japanese: "Sansho"), Nat. Ord. Rntacea\ The oil has a yellowish color, and an agreeable lemon-like odor and taste. Specific gravity 0.9T3. It i)()ils between 16(1 and 230 C, and contains a terpene and citral. NON-OFFICIAL ESSENTIAL OILS. G9 Oil of Peru Balsam, see Oil of Balsam Peru. Oil of Petit Grains. (Gcrmau : Petitgruins-Oel.) Distilled from the leaves and unripe fruits of Citni-s Bigavadia Duhamel (Nat. Ord. Rntacea'). A yellowish liquid, having an odor reminding of the oil of orange flowers (neroli), but not nearly so fine. Specific gravity 0.890-0.900. It contains the acetic ester of an alcohol which is either isomeric with linalool, or most probably identical with it. This is not the only Ijody to which the aroma of the oil is due, but it appears to be a ^-ery essential one. Messrs. Schimmel & Co. {Berichf, April, 1894, j). 39) have found the amount of ester in Paraguay oils to vary from 50 to 80 per cent., and that the oils containing the most ester are richest in perfume. The oil is soluble in twice its volume of 80 per cent, alcohol. Oil of Petit Grains is used only as a perfume. Oil of Phelhiutlrium, see Oil of Water Fennel. Oil of Pilocarpus, see Oil of Jaborandi. Oil of Pimpinella. {Germcui : Piini>iiR'll-()el.) Distilled from the root of Pimpinelhi Saxifrnga Linue (Nat. Ord. UmbeUiferce). The oil has a yellow color, and a penetrating, parsley-like odor. Specific gravity 0.959. It boils between 240' and 310 C, but appears not to have been further examined chemically. Oil of Pinus Abies or Norway Spruce Fir. (Germa)i : Fichtennadel-Oel.) Distilled froni the leaves and twigs of Finns Abies Linne (Pinus excelsa Lk., Abies e.rreJsa DC, Picea vulgaris Lk.), Nat. Ord. Coniferce. The oil has a characteristic, and exceedingly agreeable odor. Specific gravity 0.888. Optical rotation — 21° 40'. It contains laivo- gyrate pinene, Isevogyrate phellandrene, dipentene, cadinene and Isevogyrate bornyl acetate. Tlie amount of ester, calculated as boruyl acetate, is about 8.3 per cent. The interesting investigations on the coniferous oils here described, conducted by Drs. Bertram and Walbaum in the laboratory of Schim- mel & Co., Leipsic, are contained in the Arcliiv der Pliarm., 1893, pp. 290-305. See also Schinnnel & Co.'s Bericld, October, 1892, p. 21, April 1893, p. 29, and October, 1893, p. 19. 70 NON- OFFICIAL ESSENTIAL OILS, Oil of IMiius Ledebourii or Siberian Larch. {Gcrtiuin: Sibirisclies Fichtennadel-Oel.) Distilled from the leaves of Pinufi Ledebourii Endl. {Larix Sihirica Ledebour), Nat. Ord. Coniferce. Specific gravity 0.913. It boils at about 1(59' C, but appears not to have been further examined. Oil of riuus Picea or Silver Fir. {(icniKtii : Edfltiiiiiien-Oel.j Distilled from the leaves or the young cones of Piitiis Picea Linne (Abies 2M!ctlnatu DC), Nat. Ord. Coniferw. The oil from the leaves has a specific gravity of 0.87 to 0.88. Optical rotation — 20' to — 50". It contains pinene. limonene, cadinene, and bornyl acetate. The amount of ester, calculated as bornyl acetate, is about 4.5 per cent. This oil has a very agreeable, refreshing odor, and is of value in perfumery. The oil from the young cones has a specific gravity of 0.850 to 0.865. Optical rotation — 55" to — 80'. It contains pinene, limonene, and about 0.5 per cent, of ester, calculated as bornyl acetate (see also Wallach, in Liebig's Annalen, 227, p. 2S7). This oil has a milder odor than that from the leaves and twigs. Its physical characters and chemical composition are also (^uite different. Oil of Piiius Pumilio or Mountain Pine (German: Latscheakiefern-Oelor Krumniholz-Oel.) ( Oleum Ternplliiuni) . Distilled from the leaves of PUius Piunilio Hiinke (Nat. Ord. Coniferce). This oil is also known by the fanciful names of " Piimiline " and "Pinol," and by the latter designation it should not be contused with the definite chemical body CioHioO, which is an isomer of camphor, and to which the name j)inol has also been applied (see Liebig"s Annalen, 253, 1889, p. 249, and 259, 1890, p. 309). The above oil is colorless or greenish-yellow, has a peculiar, agreeably aromatic odor, and an aroiiiatic, bitterish taste. Specific gravity 0.865 to 0.870. Optical rotation — 5" to — 10". It contains pinene, phellaudrene, sjdvestrene, cadinene, and bornyl acetate. The amount of ester, calculated as bornyl acetate, is about 5 to 9 per cent. An oil distilled by IMessrs. Schimmel & Co. from the fresh twigs of Pinus Pumilio differed somewhat in its characters from the com- mercial oil, which is distilled chiefly in the Tyrolese Alps. Its specific gravity was 0.892. Optical rotation — 8'. Amount of ester, calculated NON-OFFICIAL ESSENTIAL OILS. 71 as bornyl acetate, 8.7 per cent., while the commercial oils contain on an average about 5 })er cent, of ester (see Berichi, October, 189"), p. 19). The oil has been used in nianj^ forms, both internally, externally, and for inhalations, especially in the treatment of influenza. Oil of Piiius Silvestris or Stotch Pine. (German : Kiefernnadel-Oel.) Distilled from the leaves of Pinus silvefitris Linue (Nat. Ord. ConifercH). The specific gravity of the oil from German leaves is 0.88(3, from Swedish leaves 0.872. Optical rotation +10^ to +10' 40'. It contains pinene, sylvestrene, cadinene, and bornyl acetate, the latter in amoimts of about 3.0 per cent. This oil possesses a very agreeable, and strong, pine-like odor. It is used medicinally, in the form of inhalations in lung diseases, and as an addition to baths in rheumatic affections. Oil of Poplar Buds. (Gcrtiian : Pappt'lknospoii-Oel.) Distilled from the dried buds of Populus nigra Linne (Nat. Ord. Salicacei^). The oil has a bright yellow color, and a fine odor, reminding somewhat of chamomile. Specific gravity 0.900. Optical rotation -|-2'. Boiling point 355' to 265 C. Its chemical composition corre- sponds to the formula (C5H,)x, and its boiling point therefore indi- cates it to be a sesquiterpene C15 H24 (see Ber. d. deutsch. dievi. Ges., 6, 1878, p. 890, and 7, 1874, p. 1485). Oil of Reseda. (German: Keseda-Oel.) Distilled from the flowers of Reseda odorata Linne or "Mign- onette" (Nat. Ord. Resedacete). This oil is solid at ordinary temperatures, and of a wax-like con- sistence. It appears not to have been chemically examined, but is doubtless of value in perfumery. Oil of Reseda Root has no similarity with the oil from the flowers, but possesses a radish-like odor, and contains sulphur. It appears to belong to the group of so-called mustard oils, although not identical with ordinary mustard oil. Its specific gravity is 1.085 and oj^tical rotation -j-l"" 30 (see Schimmel & Co.'s Bericht, April, 1894, p. 55). Oil of Rhodium, see Oil of Rose Wood. Oil of Rose Geranium, see Oil of Geranium. T-2 NON-OFFICIAL ESSENTIAL OILS. Oil of Rose Wood. (German : Rosoiiholz-Oel.) The article occuri-iug iu commerce under this name, or as "Oil of Rhodium, " is a mixture of sevei'al essential oils with rose oil. The true Oil of Rose Wood, which is now not obtainable, but a very small specimen of which has been distilled by Messrs. Schimmel & Co., of Leipsic, is derived from the wood of Coni'oh'uhis ticoparius Linne (Nat. Ord. Convoh-uhiceie). It has a handsome golden-j-ellow color, an exceedingly agreeable rose-like odor, and, like rose oil, solidifies at about 12 C. in needle- shaped crystals. The earlier investigations assign to this oil a specific gravity of 0.906, a la>vog\-rate rotation, and a boiling point of 249 C. It ajjpears to consist chiefly of a sesquiterpene (Schimmel & Co. 's Bcricht, April, 1887, p. 28). Oil of Rose Wood has been used in perfumer^-, and as a bait for wild rabbits and rats. For the latter purpose it is said that an equally effectual preparation is a mixture of 1 part of rose oil with 20 parts of copaiba oil. The wood of Liualoe, from French Guiana, is sometimes brought into commerce under the name of Bois de Rose feineUe. Oil of Rue. iGcniia)} : Kauten-Oel.) Distilled from the leaves of Ruta grairolois Linne (Nat. Ord. Rictaccce). The oil has a yellowish or greenish -yellow color, and a character- istic, not specially agreeable odor. Specific gravity 0.834 to 0.840. Optical rotation about -f-1' to -|-2". At 0' C. it solidifies to a crystalline mass. It begins to boil at about 215" C, and distills completelj^ at about 235' C. It contains about 90 per cent, of methyl -uonyl ketone CH3-CO-C;, Hi9. The latter is a colorless litjuid, having an agreeable odor, a specific gravitj' of 0.831, boiling point 226 to 227' C, and which solidifies at 10' C. to a crystalline mass. The oil is used medicinally, both internally and externally. It is frequently adulterated with oil of turpentine, petroleum, alcohol, etc. Oil of Sage. (Geiinan : Salboi-Oel.) Distilled from the leaves of Sfdi'ia ojlficiiialis Linne (Nat. Ord. Lab lata'). A yellowish or greenish-yellow liquid, having the penetrating, characteristic odor of sage. Specific gravity 0.915 to 0.925. Optically dextrogyrate. The oil contains small amounts of pinene and ciueol, but NON-OFFICIAL ESSENTIAL OILS. 73 its chief coustitueut is thujoue C,,) H,,. O (formerly termed .saivial), which also occurs in the oils of thuja, tansy, and wormwood (see Liebig's Annaleii, 237, 1885, p. 289, and 252, 1889, p. 94). The oil is used to a small extent medicinally. Oil of Satiireja. (Giriiiaii : iSatureja-Oel.) Distilled in southern Spain from the herl) of Satnreja Tliymbva (Nat. Ord. Labiatce). The oil has an exceedingly strong and penetrating, thymol-like odor. Specific gravity 0. 906. It consists for the most part of cymol, with about 19 per cent, of thymol, and some pinene, dipentene, and bornyl acetate. It has the properties of a powerful stimulant and antiseptic. See also Oil of Summer Savory. Oil of Scurvy Orass, see Oil of Cochlearia, Synthetic. Oil of Serpentaria. (G(r)naii : Schluugenwurzel-Oel.) Distilled from the rhizome and roots of Aristolochia Serpentaria Linne and A. reticulata Nuttall, "Virginia Snakeroot " (Nat. Ord. Aristolochiacea^). The oil has an amber or light brown color, and an odor re- sembling that of camphor and valerian. Specific gravity 0.975 to 0.988. Optical rotation — 4". It is stated by J. C. Peacock {Ainer. Journ. Pharm., 1891, p. 257) to contain a terpene (probably pinene), an ester of borneol, a body of tlie composition CimHsuO, and a green or bluish-green fraction. Oil of Snakeroot, Canada, see Oil of Asaruni Canudense. Oil of Snakeroot, Virginia, see Oil of Serpentaria. Oil of Spice Bush. (German: Spicebush-Oel.) Distilled from the bark, berries, leaves, and twigs of Lindera Benzoin Blume (Nat. Ord. Lauracece). The plant is known also as Fever-hush, Benjamia-hush, or Wild Allspice. The oil frouT the hark has an odor reminding of wiutergreeii, a specific gravity of 0.923, and lioils between 170 and 300 C. The oil from the herries has an aromatic, sjncy, and camphoi'-like odor, a specific gravity of 0.855, and boils between 160' and 270 C. The oil from the leaves has a very agreeable, lavender-like odor, and a specific gravity of 0.888. U NON-OFFICIAL ESSENTIAL OILS. Tlie oil from the ficiys ]ias an odor reiiiinding of caniplior and calamus, and a specific gravity of 0.928. None of these oils appear as yet to have been cliemicany examined. Oil of Spike, see Oil of Lavender, Spike, under {German : Spik-Oei.) Oil of Laveiider Flowers, Part I. Oil of Spruce. ((Jeriiuin : Spruee-Ool.) This oil is distilled fnnn the leaves and twigs of either Picea itlba Link. {White Spruce) or Picea nigra. Link. (Black Spruce), Nat. Ord. Conifercp. It is a colorless liquid, having a characteristic and agreeal)le odor. Comjnercial oils from authentic sources we have found to have a specific gravity ranging from 0.905 to 0.912, and an optical rotation of —22^ 20' to —25' 50'. This Oil of Sj)ruce is apparently the pnxluct which was examined in the laboratory of Messi"s. Schinimel & Co., Leipsic, and designated as "Hemlocktannen-Oel," with reference to its supposed botanical source from Abies canadensis Michx., which is jjopularly known in America as "Hemlock Spruce. ' The latter, however, is lielieved to be the source of the commercial Oil of Hemlock, which is probably similar in composition to the true Oil of Spruce. The above described Oil of Spruce must therefore be considered to contain lajvogyrate pinene, cadineue CiiHo4, and l)ornyl acetate, the latter in amounts of about 3.6 per cent, (see Schinimel & Co.'s Bericld, April, 1893, p. 30). Compare also Oil of Hemlock. Oil of Star Anise, see Oil of Anise, Star. Oil of Storax. (Oc'idffH ; Stora.\-Oel.) Distilled from Storax, a balsam prepared from the inner bark of Liquidambar orienfalis Miller (Nat. Ord. Hamamelacefv). This oil has a specific gravity of 0.890 to 0.900, and an optical rotation of — 15'. It contains styrol C, H5-CH=CH.j, and several esters of cinnamic acid. It boils between 150" and 300 C, with de composition, and the separation of cinnamic acid. It is of value in perfumery, and for this purpose is capabie of completely displacing storax balsam. Through improved methods of distillation, the oil now prepared by Messrs. S^^'himmel & Co. is partic- ularly rich in its most valuable odorous constituents, A\-hich are the less volatile esters (see Berichf, April, 1894, p. 52). ! NON-OFFICIAL ESSENTIAL OILS. 75 Oil of Sunibul. (GcvDtan: M(iSfliuswurzcl-(_)c; ) Distilled from the root of Fei-ida Saiithul Hooker filius, or so-called Musk Root (Nat. Ord. Uiiibellifera). Tliis oil has a strong odor, resembling that of musk, for which it is sometimes used as a substitute. Its specific gravity is 0.954. Nothing appears to be known of its chemical constituents. Oil of Summer Savory. {(Icrumn: Bohnenkraut-Oel.) Distilled from the fresh herb of Satureja liortensis Linue (Nat. Ord. Lahiatce). A yellow, limpid liquid, having an aromatic, thyme-like odor. Specific gravity 0.898 to 0.913. It contains carvacrol C10H14O (about 80 per cent.), traces of another phenol, cymol doHn, and a terpene liaving a boiling point of 178" to 180' C. (see Ber. d. deutsch. cheiii. Ges., 15, 1882, p. 816). Compare also Oil of Satureja. Oil of Sweet Fern. (German : Comptoni;i-Oel.) Distilled from the leaves of Myrica afipleaifoJia Endl., or Comp- tonia af^plenifolia Alton (Nat. Ord. Mijricacecv). This oil has a strongh' spicy, cinnamon-like odor. Specific gravity 0.926. In a freezing mixture it becomes solid. It has not yet been further examined. Oil of Tansy. (German : Rainfarrn-Oel.) Distilled from the herb of Tanacetum vidgare Linne (Nat. Ord. Composit(v). A yellowish liquid, becoming brown on exposure to light and air, and having a strong odor. The specific gravity of the oil from fresh herb is 0.915 to 0.930, and that from dried herb 0.954. It contains a ketone termed tanacetone CioHieO, which is identical with thujone from thuja oil, and which also occurs in the oils of sage and worm- wood. The oil also appears to contain tanacetyl alcohol CioHibO, and a small amount of a terpene (see Ber. d. deutseh. ciem. Ges., 11, p. 450, 25, pp. 3343, 3352, 3513; also Schimmel & Co.'s Bericht, April, 1893, p. 50). We have observed that the oil forms a perfectly clear solution with three times its volume of 70 per cent, alcohol, which may serve as an excellent practical test for its jmrity. It has de- cidedly poisonous properties. 7'i NON-OFP^ICIAT. ESSENTIAL OILS. Oil of Thuja. {(JfriiKin : Thuja-Oel.) Distilled from the leaves of Thuja occidentalis Limie, the so-called Arbor Vit.e or White Cedar (Nat. Ord. Coniferce). A pale yellow licjuid, having a characteristic, rather agreeable odor. The commercial oil from authentic sources has been found to have a specific gravity varying from 0.915 to 0.9'2.j, and an oirtical rotation of — 8 to — 14 C. An oil distilled in ovir Garfield factor}- has a specific gravity of 0.932, ajid an optical rotation of — 6 10'. The oil contains thujone CioHi,;0, which is also found in the oils of tansy, sage, and wormwood, together with l^vogyrate fenchone CioHieO, pinene, and apparently some inactive carvol (see Liebig's Amialeit, Bd. 272, p. 99, Bd. 277, p. 159; also Schimrael & Oo.'s Bericht, April, 1893, p. 57, April, 1894, p. 52j. The oil of thuja forms a perfectly clear solution with 8 times its volume of 70 per cent, alcohol at about 20 C. This test is of practical importance, as serving to distinguish this oil from the Oil of Red Cedar leaves (from Juniperus Virginiana Linne), which is not soluble in 70 per cent, alcohol. Compare Oil of Cedar Leaves, American. Oil of Thuja Root. i; (German : Thuj;nvnr/.el-Oel.) Distilled from the root of Tliuja oriental is Linne (Nat. Ord. Conifera'). This oil has an intense brown color, ami an odor reminding of thymoquinone. Its si)ecific gravity is 0.979. It has not been further examined. Oil of Thyme, Wild, see under Oil of Th.vme, Part I. Oil of Tolu Balsam, see Oil of Balsam Tolu. Oil of Valerian. iGcDiiiiii : lialdriiUi-Ool.) Distilled from the rhizome and roots of Valeriana officinalis Linne (Nat. Ord. Valerianacea'). This oil was recognized by the U. S. Pharmacopceia of 1880, but is now discarded from the oftitdal list. It has a yellowish or brownish color, and a characteristic, penetrating odor. Specific gravity 0.940 to 0.950. It contains pinene, camphene, borneol, and the formic, acetic, and i.so-valerianic esters of borneol (see Ber. d. cleutsch. cliem. Ges., 11, 1878, p. 452, and Compt. rend., 117, p. 1096). It is used medicinallj^ in various nervous affections. NON-OFFICIAL ESSENTIAL OILS. 77 Oil of Yaleriaii, Japanese. [Kesso Oil.] {German: Haldrian-Oel, Japunisclies.) Distilled from the rhizome aud roots of Valeriarm officiudlis Liune, var. cmguHtifolia Miq. (Nat. Ord. Valerianacece). This oil has a green color, a somewhat thickish consistence, and can scarcely be distinguished in odor from the ordinary oil of valerian. Specific gravity 0.996. It contains Itevogyrate pinene, camphene, di- pentene, terpineol, borneol, the acetic and iso-valerianic esters of borneol, kessyl acetate C^ H23 O-Co Hs O-,, probably also a sesquiterpene CioH^j, and in the high boiling portions a blue oil (see Archiv der Phann., 228, p. 4.S3. and Journ. fiir praM. Chemie, N. F., 49, 1894, p. 18. The uses of this oil are the same as those of the ordinary oil of valerian. Oil of Yaleriaua Celtica. [German : Speik-Oel.) Distilled from the root of Valei'iana vcltica Linne (Nat. Ord. V(ilerianacea'). Tliis oil has a strongly aromatic odor, reminding more of Roman chamomile and patchouly than of valerian oil. Specific gravit.v 0.967. It boils between 250' and 300" C, but appears not to have been further examined. It has been used as a perfume in soaps, etc. Oil of Yerbeiia, East Indian, see Oil of Lemongrass. Oil of Terbena, Java, see Oil of Citronella Fruit. Oil of Tetiver. [Cuscus Ciil.] ((_lcvuM)t : Vetiver-Oel.) Distilled from the root of Andropogon muricatus Eetz (Nat. Ord. Graniinea'). The oil is thickish, and has a strong and very agreeable odor, reminding somewliat of violet. Specific gravity 1.01 to 1.02. It is soluble in twice its volume of 80 per cent, alcohol. Nothing appears to be known of its chemical composition. It is used in perfumery. Messrs. Schimmel & Co. {Beridit, April, 1893, p. 59, and April, 1894, p. 53) have found that the oil distilled in the island of Reunion cannot serve as a substitute for the oil distilled from the Indian root, and with modern appliances. The Beunioa vetiver oil has a much milder odor, a specific gravity of 0.968, and is insoluble in 80 per cent, alcohol, these characters indicating its adulteration. 78 XOX-OFFICIAL ESSENTIAL OILS. Oil of Viruiniji Snake Root, sec Oil of Serpeiitaria. Oil of Walnut Leaves. (Gcrnmn : KussblUtter-Oel.) Distilled from the fresh leaves of Juglans regid Linne (Nat. Orel. JucjUmdacetfi). This oil has an agreeable, tea-like odor, and is solid at ordinary temperatures. It has not yet been further examined. Oil of IVater Fennel. (Gcrnuin : Wassorli'iichel-Oel.) Distilled fi*om the fruit of Phellandrinm aqiiaticnm Linne (Nat. Ord. Umbelliferce). The oil is yellow, limpid, and has the peculiar odor of water- fennel. Specific gravity 0.860 to 0.890. It contains pinene, pliellan- drene, and dipentene (see Gazetta Chivi. ItaL, XVI, p. 225). Oil of Water Mint. (Germa)i : AVasscimiuz-Oel.) Distilled in southern Spain from the fresh herb of Mentha (iqutttica Linne (Nat. Ord. Labiatce). The oil has a yellowish-green color, and an odor reminding of pennyroj'al. Specific gravity 0.880. Optical rotation — 2 14'. Oil of White Ash Bark. {German: Eschenrinden-Ool, Amerikanisches.) Distilled from the bark of Fra,rinns Aviericdud Linne (Nat. Ord. Oleacecv). This oil has a characteristic, fruit-like odor, and a l)utter-like consistence at ordinary temperatures. It has not yet been further examined. Oil of White Cedar, see Oil of Thuja. Oil of Wild Carrot, see Oil of Carrot, Wild. Oil of Wild Cherry Bark. (German : Wildkirschenrinde-Oel.) Distilled from the l)ark of Pninus serotina Ehrhart (Nat. Ord. " Rosacea'). This oil resembles that of bitter almonds. Specific gravity 1.050. It consists for the most part of benzaldehyde, and is rich in hydro- cyanic acid. Oil of Wild (iini^er, see Oil of Asarum Canadense. NON-OFFICIAL ESSENTIAL OILS. 79 Oil of ^\m 3iiiit. Distilled from the dried herb of Mentha Canadeni^is Linne (Nat. Ord. Lahiafcf). The oil has a reddish -j^ellow color, and an odor reminding of pennyroyal. Specific gravity' 0.948 at 15' C. It forms acinar solution with twice its volume of 70 per cent, alcohol. Its chemical compo- sition has not yet l)een determined. Oil of AViia Thyme, see under Oil of Thyme, Part I. Oil of Winter's Bark. (German : Wiiitcrsriiidt'ii-Oel.) Distilled from the bark of Drirnys Winteri Forst. (Nat. Ord. 3IagiioIlace(v). Specific gravity 0.945. Its chief constituent appears to be a hydro- carbon boiling between 260 and 265 C, and therefore probably a sesquiterpene, but it has not yet been suflficiently examined. Oil of Wormseed, Levant. (Gcnmin : Zittworsainen-Oel.) Distilled from the unexpanded flower heads of Artemisia pauci- flora Weber (Nat. Ord. Conipositce). The oil has a yellowish color, and a penetrating, disagreeable odor. Specific gravity 0.930. It consists chiefly of cineol CuHi^O, with some dipentene (see Liebig's Anualen, 225, 1884, p. 291). It is used to a small extent medicinally. When taken in any con- siderable amount it possesses marked toxic ijroperties. Oil of Wormwood. (German : Wermuth-Oel.) Distilled from the leaves of Artemisia Absiiithiam Linne (Nat. Ord. C'oiiqjosita'). The oil from the fresh herb has a dark green color, while that from the dry hei'b is yellowish -green or yellowish-brown, always becoming dark brown, however, by age. It has a strong and some- what unpleasant odor, resembling that of the plant. Specific gravity 0.925 to 0.950. Its chief constituent is thujone (absynthol) CioHieO, which is associated with a small amount of terpenes, and a deep blue oil in the higher boiling portions (see Liebig's Aiinaloi, 170, 1873, p. 290, and Ber. d. deutsch. diem. Ges., 25, p. 3350). The oil is used to a small extent medicinally, but also po.ssesses strongly toxic properties. Oil of Yarrow, see Oil of Milfoil. 80 NON-OFFICIAL ESSENTIAL OILS. Oil of Ylang YlaiiJ^. {(icrman : Ylanjr- Ylang-Oel.) Distilled in ^Manila from the flowers of CaiuuKjd odordta Hooker til. et Tlioinson (Nat. Ord. Anonacen'). This oil is noted for its delicious perfume, especially the brand known as "Sartorius," which represents the finest attainable quality. Specific gravity 0.940 to 0.9oo. Optical rotation — 45" to — 60\ It contains an ester of benzoic acid, and, according to the recent re- searches of Beychler {Bull. Soc. Chim., 1894, 11-12, p. 407), an alcohol of the formula d,, H,^ O, and a sesquiterpene. The alcohol, which has been designated as "Ylangol," appears to bear some relation to geraniol. It boils l)etween 103 and 107' C, under a pressure of 28 Mm., has a specific gravity of 0.88f) at 15" C, and on oxidation with a chromic acid mixture yields a small amount of a substance having an odor resembling citral. (See also Oil of Cananga, Java.) Oil of Zedoary. {GcnmiH : Zittwerwurzel-Oel.) Distilled from the rhizome of Cnrcnma Zedoaria Roscoe (Nat. prd. Zingiheracca'). The oil has a pale yellow color, and a camphor-like odor. Specific gravity 0.992. It contains cineol, CioHi^O. PART III. ORGANIC CHEMICAL PREPARATIONS. Acetic Ether, see Ethyl Acetate. Acid Acetic, Grlacial. Acicluiii Aceticuiu Glaciale. {German : Eisessig.) C2 H^ O3 or CH3-COOH. Nearly or quite absolute Acetic Acid, corresponding to the chai'acters and tests described in the U. H. Pliarmacopre-ia, 1890. Amyl Acetate. c,h,:-('-..h.o.. (German: Amylacetat.) This preparation consists chiefly of iso-amyl acetate, which is a colorless, neutral liquid, having an agreeable, pear-like odor, and is thei'efore sometimes known as "Pear Oil." Specific gravity 0.875 at 15" C. Boiling point about loS'" C. Amyl Biityrate. c.Hu-C.h.o,. [German : Amylbutyrat.) This x^repara-tion consists chiefly of iso-amyl butyrate, which is a colorless liquid, having an agreeable, apricot-like odor. Specific grav- ity 0.852 at 15' C. Boiling point about 178= C. Amyl Formate. c,H.,-CHO.. (German : Amylformiat.) This j)reparation consists chiefly of i.so-amyl formate, whicli is a colorless li(iuid, having a fruity odor. Specific gravity 0.874 at 21 C. Boiling point about 123" C. Amyl Nitrite, an,, no.. Amy! Nitris. (German : Amylnitrit.) The official preparation represents a liquid containing aliout 80 per cent, of amyl (principally iso-amyl) nitrite, together with variable quantities of undetei-mined compounds. 81 82 ORGANIC CHEMICAL PREPARATIONS. It is "a clear, yellow or pale yellow liquid, having- a peculiar, ethereal, fruity odor, and a puugent, aromatic taste. Si)ecific gravity O.tSTO to 0.880. It is A-ery volatile, even at a low temperature, and is inflammable, l)uruing with a fawn-colored flame. It boils at about 0(5" to 99 C, yielding an orange-colored vajKn-."' ^Ve have succeeded in producing this preparation in a degree of purity which is rarely met with in a commercial article. Our product has a specific gravity of 0.8789 at 15' C, and, when assayed by the ofticial gasometi-ic method, yields an amount of nitric oxide corresponding to 100 per cent, of pure amyl nitrite. Amyl Nitrite is a very important and active medicinal agent. Aiiiyl Talertauate. c. H,,-( ., h. o.. {German : Amylvalerianat.) This preparation consists chiefly of iso-amyl valerianate, whicli is a colorless liquid, having an agreeable odor, resembling that of apples, and is therefore sometimes known as "Apple Oil." Specific gravity 0.879 at 0^ C. Boiling point about 188° C. Aliethol . t '. H,. O or Ce H4 ■; ?S"cH-CH..,. [Para-methoxy-proi)enyl-benzol.] (German: Anethol.) This substance represents the essential constituent of the oil of anise in a state of the greatest i^urity, and is especially characterized ))y its pure anise flavor and fine aroma, as also by the following physical properties : It is absolutely' colorless, melts at 21" to 22° C, and has a specific gravity of 0.985 at 25° C. It lioils at 234° C, and is optically inactive. The definite cliaracters of auetliol render it wAl adapted to dis- place with advantage the oil of anise for all purposes for which the latter is used. Anisic Aldehj de {Anbepfne). C. H. O.., or C, H, (OCH:0 COH. {Geniiaii : Aiiisaldehyd.) This substance resembles in odor the blooming Hawthorn (Cra- tcegus). It is a definite chemical body, having the following characters: A clear, colorless liquid. Si)ecific gravity 1.126 at 15 C. Boiling point 245° to 246° C. At ordinary temperatures it is licjuid, but solidifies in a freezing mixture to a solid, crystalline mass, winch melts at — 4° C. If it be carefully cooled to — 10 C. it still remains liquid, l)ut will at once solidify on bringing in a trace of ciystallized anisic aldeliyde, when the temperature rises to — 4' C. On exposure to the air it oxidizes readily to anisic acid, and should therefore be kept in well-stoppered liot ties, which should be as completely filled as possible. It is readily soluble in alcohol, and is nsed in perfunierv and in soaps. ORGANIC CHEMICAL PREPARATIONS. 83 Apiol. C,,Hi4 04. (German : Apiol.) This is a constituent of the Oil of Parsley, from the fruit of Apium PetroseliiiiiDi Linne {Petroselinum sativum Hoflfm.). It forms handsome, needle-shaped crj'stals, which melt at 30° C, and should therefore be kept in a cool i^lace (see Ber. d. deidsch. chevi. Geti., 21, pp. 1621, 2516; 22, p. 2481 ; 23, p. 323). It has been used to some extent as a substitute for quinine. Benzoic Ether, see Etliyl Beiizoate. Benzyl Acetate. c„ h.-ch. -c... h. o.. (Gcrma)i : Benzylacetat.) A colorless liqiiid, having an aromatic, i)ear-like odor, especial!}' Avlieu diluted. Specific gravity 1.057 at 16.5" C. Boiling point 206' C. Berganiiol, see Linaloyl Acetate. Bntyric Ether, see Ethyl Bntyrate. Borneol {Borneo Camplior, Artip'cial). Ci„Hi7-0H. (Gennan : Borneol.) This is a handsomely crystallizable suljstance, having an odor quite different from that of common camphor, and reminding some- what of patchouly and ambergris. It melts at 203° to 204° C, and boils at 212° C. It is readily soluble in alcohol, but almost insoluble in water. Borneol i)ossesses antiseptic properties, and is also adapted for use in perfumer}'. Iso-horneol. Tliis body, as its name indicates, is an isomer of the above described borneol. Its odor is also more agreeable than tlie latter, reminding of tansy and sage, and it also shows marked differences in its solubility in benzol and petroleum beuzin, and in its chemical deportment. It melts at 212" C. (in a closed tube). By dehydrating agents it is converted into camphene CioHie, and by oxidation it forms ordinary camphor CioHie O (see Bertram and Walbaum, in Jouni. fur xirakt. Cliem., N. F., 49, 1894, pp. 1-15; also Conq^t. rend., 118, p. 248; and Schimmel & Co.'s BericJif, October, 1893, p. 54, April, 1894, 13. 66). It has also been shown by Bertram and Walliaum that the borneol of commerce, which is obtained by the reduction of connnon camphor with sodium, is not a simple body, but a mixture of borneol and iso-l)orneol, in wliich tlie former predomi- nates. Borneol or Borneo Camphor occurs as a natural product not only in the wood of the tree known botanically as tlie Dryobalanopa aroDiatica Giirtn. (Nat. Ord. Dipterocarpece), l)ut has also been found, 84 ORGANIC CHEMICAL PREPARATIONS. cliietly iu the form oi: esters, iu tlie following essential oils. Oil of Rosemary, Satm-eja, Spanish Thj-me {Tliynius capitntus), Valerian, Japanese Valerian (Kesso), Picea alba (Spruce), Abies sibirica. Pi tins Picea, Pinus Pninilio, Pi)iiis sijlvestris, and CitroneUa. The so-called Blumea Camphor or "Ngai" Camphor of the Chinese, from Blumea bulsamifera DC. (Nat. Ord. CompoHitce), has the same composition as Borneo Camphor, and ajipears to be identical with it, with the exception that it is optically lajvo-rotatory in about the same degi'ee that Borneo camphor is dextro-rotatorj'. Boni.vl Acetate. c,uH„-c.h.o.. {Ocrtiutn : IJornylaoetat.) Tliis body is found in many of the pine-needle oils, and possesses the characteristic aroma of the latter. It crystallizes iu rhombic prisms, which melt at 29° C, and are readily soluble in alcohol. Specific gravity 0.991 at 15° C. It boils at 106' to 107° C. under a pressure of 15 Mm. It is admirably adapted for replacing the pine oils in con- fections, etc. Boriiyl Formate. Cu,h>,-cho.. {German: Bornylformiat.) This body is liquid, but its odor resembles that of tlie preceding acetate. Specific gravity 1.017 at 1")' C. It boils at 98^to 99' C. under a pressure of about 15 Mm. Boruyl Yaleriaiiate. Cn.Ho-c.H^o,. (Girnuin : Bornyivalerianat.) This body is an essential constituent c^f the oil of valerian, and probably possesses the action of the latter to an increased e.xtent. Specific gravity 0.956 at 15' C. It boils at 128' to 130' C. under a pressure of abovit 10 ]Mm. Butyl Acetate, c, h„-c. h. c. {German : Butylacetat.) This preparation consists chiefly of iso-butyl acetate, wliich is a colorless liquid, having an agreeable, banana-like odor. Specific gravity 0.8845 at 16° C. Boiling point 116' C. Butyl Butyrate. c.h„-c,h,o.. {(li:riiuin : lUuylbutyrat.) This preparation consists chiefly of isobutyl butyrate. It is a colorless liquid, having an agreeable, fruity odor. Specific gravity about 0.870 at 15' C. Boiling point about 157' C. ORGANIC CHEMICAL PREPARATIONS. 85 Butyl Iso-sulpliocyaiuite, see Oil of Coelilearia, Synthetic, Part II. Butyl Valerianate. C. H„-C. H. o.. (German : Butylvalerianat.) This preparation consists chiefly of iso-butyl valerianate. It is a colorless Ii(piid, having an agreealile, frnity odor. Specific gravity about 0.860 at 15^ C. Carvacrol. C,„h,.-oh or c. h.. c^^^z^ff^'^yiUiH:.. [Oxy-cymoL] (German : Carvacrol.) Tliis is the essential constituent of the Oil of Origanum, Cretian, and is also found in the Oils of Thj'ine and Sunnner Savory. It is a thickish, aromatic liquid, which solidities at — 25 C, and is isomeric with carvol. Specific gravity 0.981 at 15' C. Boiling point 236' to 337' C. Its alcoholic solution is colored green, by ferric chloride. Carveiie. CioHi„. (German : Carven.) This hydrocarbon is found in the Oil of Caraway, and is identical with dextrogyrate limonene. Specific gravity 0.850 at 15' C. Boiling point 175" to 176' C. €arvol. Cu,Hi,0 or c.H,.cCH.CH.. (German: Carvol.) This body, which is chemically a ketone, is the essential constituent of Oil of Caraway, and is also found in a dextrogyrate form in the Oil of Dill, while its lajvogyrate modification occurs in the Oil of Spear- mint. It is officially recognized by the German Pharmacopoeia, which describes it as follows: "A pale yellowish or colorless liquid, having a fine odor of caraway. Specific gravity 0.960. Boiling point 224' C. 1 Cc. of carvol, diluted with 1 Cc. of alcohol, should either not be changed or assume only a slight reddish or violet color on the addition of a drop of solution of ferric chloride." The latter solution should for this j)urpose be quite dilute. Carvol possesses all the valuable properties of the Oil of Caraway in a perfectly pure and definite form. It also has the advantage over the latter oil of being much more freely soluble in diluted alcohol. Citral. Cn,Hu,o. (German : Citral.) This body, as its name indicates, is cliemically an aldehyde, and represents in a state of the greatest purity the delightful aroma of 86 ORGANIC CHEMICAL PREPARATIONS. lemuu oil, l»eliig contained in the latter to the amount of ahout 7.5 per cent. It is a goldeu-yellow li^inid, liaviug a specific gravity of 0.899 at 15" C. It boils at 116^ C under a pressure of Ki Mm., or, when perfectly pure, at 228" to 229' C. under ordinary pressure, without decomposition. By means of the special aldehyde reaction described under CitroneUal, Citral maybe converted into the so-caHed citnjl-.i-niqjhto- cinclioninic acid, CioHe^Q-.'^-H"^"' ^vhich forms lemon-yellow lamina?, fusing at 197^ C. "^^^^ Citral has the advantage of being much more freely soluble in diluted alcohol than the oil of lemon, but is best used in combination with the latter in order to obtain the desired freshness of aroma. This may be attained by mixing 1 part of Citral with 15 parts of pure Oil of Lemon, and this combination is equivalent in strength and aroma to twice its Aveight of good lemon oil. To protect Citral from change it .shouM b(^ kept in a cool aiid dark place. Besides being an essential constituent of the oil of lenion, Messrs. Schimmel & Co. have found Citral to occur in the oils of the fruit of Citrus Liiuettii Risso (Liune), Citrus Madurensis Loun. (Mandarin), Tetrantherd citrata Nees (Citi'onella Fruit), Xatdho.vylum piperitnm DC. (Japanese Pepper), and in the oils of Andropogon citrat^is DC, Eucalyptus Stairjcriaua, and Bockliausia cifriodora {Bertcht, April. 1891, p. 52). CitroneUal or Citroiiella Aldeliyde. < .h.o. (German : Citronellaldchyii.) This body occurs in the Oil of Citronella, Oil of Eucalyptus macidida, var. citriodora, and in very small amount in the Oil of Lemon. It was formerly regarded as a ketone, and therefore received the designation citroneUone (see Schimmel & Co.'s Bericht, October, 1888, p. 17). It is a colorless liquid, having a very agreeable, somewhat lemon- like odor, i-eminding also of citronella oil, but much finer than the latter. Its specific gravity is about 0.880 at 15" C. It distills between 205' and 210" C, with slight decomposition {BeHcht, October, 1890. p. 21). Compare also Seimnler, in Ber. d. deidscli. cliem. Ges., 24, p. 209. 26, p. 2254; Kremers, in Amcr. Chein. Journ., XFV, p. 208; and Dodge, Ibidem, XI, p. 456, and XII, p. 553. An aiiparently specific, and therefore very valuable reaction for aldehydes, by means of which they may be detected in essential oils ORGANIC CHEMICAL PREPARATIONS. or separated therefrom in the form of well crystallizable compounds, has recently been jjroposed l»y O. Doebner (see Ber. d. deutsch. chein. Ges., 27, 1894, p. 352). It depends ujion the formation of a-alkyl-/3- naphtocinchouinic acids, by bringing together a molecule of the alde- hyde with a molecule each of iiyro-racemic acid and /S-uaphtylamine. The reaction appears to be characteristic of the aldehydes and does not take place with other bodies which likewise contain a carbonyl group, CO, such as ketones, lactones, and the anhydrides of dibasic acids. Thus citrouella aldehyde forms the so-called citroneUone-j3- naphtociuchouimcacklC.oB.e^cJc^''^'''' which crystallizes in color- less needles, fusing at 225' C. COOH CH.O. or C.H4<^^ - V*' CH = CH. Cumarin, Synthetic. (Girinaii : Cumarin.) This is the aromatic or odorous principle of the Tonka Bean, and is found also in the Sweet Clover {Melilofus), and in the numerous other plants enumerated below. Cumarin is a definite chemical substance, and that produced by us synthetically is perfectly identical in every respect Avith the same substance obtained from any of its various natural sources, while .having the advantage of absolute purity. It forms small, colorless crystals, which fuse at 67' C. On account of its exceedingly agreeable odor, it has become a very important article in the manufacture of perfumery, for perfuming soaps, etc. , and may replace with advantage the Tonka Bean, wherever the latter has heretofore been used. It is soluble to a greater or less extent in most of the ordinary solvents. The following table, re- presenting its solubility in alcohol of different percentage strengths, and- in water, at different degrees of temperature, will be found practically usef nl : lOO Parts of Alcohol Dissolve at 0° C. Dissolve at 16 to 17° C. Dissolve at;i9to30°C'. Of 90 per cent, bv volume " 80 " " •' " 7 1 parts 6.0 " ■ 4.4 " 3.2 " 1.7 " 0.7 " 0.3 " 0.2 •' 0.15 '■ 13.7 parts 12.3 " 9.1 " 6.0 " 3.4 " 1.5 " 0.6 " 0.4 " 0.25 " 42.5 parts 38. 3 ' ' " 70 " " " " 26.0 " " 60 " " " " 16.0 " " 50 '• " " " 8 9 " " 40 " " " " 3 9 " " 30 " " " " 17 '• 20 " " " " " 10 " " " " 0.8 " 5 100 Parts ot Water 0.12 •■ 0.18 " 0.27 " The Avide distribution of Cumarin in the vegetable kingdom is indicated by the following enumeration of the plants or parts of plants in which it has thus far been found: I 88 ORCJAXIC CHEMICAL PREPARATIONS. ORCHIDACEiE. Caryophyllace^ RUTACE.-E. Legujunos^. FiLiCES (Polypodiaceae). Adiantlni.in pedatum Lixine (Herb). " peruvianuin Linue (Herb). " trapeziforme Linne (Herb). Dr)jnan'(i, Wildenoi'i (Herb). P.\LJL«. Plioenix dactylifera Linne (the common Date). Gramine^e. Anthoxanthum odoratnm Linne (Herb). Ataxia Horsfeldii (Herb). Cinna arundinacea Linne (Herb). Hierochloa alpina R. & S. (Herb). australis R. & S. (Herb). " borealis R. & S. (Rhizome). Milium effnsum Linne (Herb). Aceras anthropophora R. Br. (Herb). Angrecum fragvans Thouars (Leaves). Nigritella angustifolia Rich. (Herb). Orchis fusca Jacqu. (Herb). Herniaria glabra Linne (Herb). Rata grnvedlens Linne (Herb). Copaifera SalikoiDtda Heckel (Ripe Seed). Dipterix odorata AVilld. (Rii)e Seed). " opposiiifolia Willd. (Ripe Seed). " Pteropits Mart. (Ripe Seed). 3Ielilotus albvs Desr. (Flowers and Herb). " o/h's.s2H«i.sThuillier(Flowers&Herb). " hamatus Stocks. (Flowers & Herb): ' ' leucanthus "W. & A. (Flowers & Herb). " officinalis Desr. (Flowers and Herb). Tohiifera Balsariuna Miller (Fruit). Apocynace^. Ahjxia stellafa R. & S. (Bark). RuBiACE^. Aspcrida odorata Linne (Herb). Galium triflorum Michx. (Herb). Composite. Liatris odoratissima Willd. (Herb). " spicata Willd. (Herb). Agcratum mexicanum Sims (Herb). Oyiiiol or Cymeiie. c.Hm or CoH4<^J'^. [Para meth.yl-isoproii.vl l)i'ii7,nl.] (Gcrincni: Cymol.) This lij'drocarbon occurs in the oils of cumin, tliyme, ajowan, and some other essential oils. It is a colorless liquid, having an agreeable odor. Specific gravity 0.8GT8 at 12 C. Boiling point 175" to 176" C. Etlier, Oenailtliic {Cognac Oil, Artifcial). {(iiTmiiii : ( )cn;uit bather or Kiinstlichcs Cog-nac-Oel.) Tliis consists t)f the ethyl esters of the higher monobasic fatty neids. It is a colorless, oily lic^uid, having a characteristic cognac like i i^ ORGANIC CHEMICAL PREPARATIONS. 89 odor. It has in recent years been cousiderablj- employed, for imparting a fruity aroma to soaps, and a specially agreeal)le effect is produced by mixing it with a little Peru balsam, and the oils of cassia and lavender. Ether, Sebacic. (C..h,o.c,„h.„o.. (German : ScbacinsiiureiithGi'.) A colorless or slightlj^ yellowish liquid, having a slightly aromatic odor. Specific gravity 0.968. Boiling point 311° C. at 762 Mm. barometric pressure. Etliyl Acetate {Acetic Ether). Aether Aceticus. (German: Aethylacetiit. Essigiither.) C2Hr.-C2H3*>2. This preparation is recognized by the U. S. Pharmacopceia, 1890, to which reference may be made for a full description of its characters. The article supplied by us is perfectly pure, and meets all the official re- quirements, which is not the case with much of the commercial article. Ethyl Beiizoate (Benzoic Ether). C.H,-C.H.O.. (German : Aethylbenzoat.) A colorless, aromatic liqviid. Specific gravity 1.055 at 15' C. Boiling point 212' to 213° C. Ethyl Butyrate {Butyric Ether). C H.-C. H, O.. (Germein : Aethylbtityrat.) A colorless, neutral liquid, possessing in a diluted condition an agreeable, pineapple-like odor and taste ; it is therefore sometimes known as "Pineapple Oil." Specific gravity 0.900 at 18 C. Boiling- point 120' to 12r C. It is used for imparting flavor to confections and lieverages. Ethyl Formate {Eormic Ether). C h.-cho.. (German : Aethylformiat.) A colorless, very limpid, neutral liquid, of ag'reeable odor. Specific gravity 0.915 at 15' C. Boiling point 54 to 55' C. Ethyl Nitrite {Xitrous Ether). CH.no,. (German: Aethyliiitrit. Salpetrig-sauro Aethylathor.) Pure ethj-l nitrite is a mobile liquid, having a penetrating, but agreeable, apple-like odor. It has a sjiecific gravity of 0.900 at 15 C, and boils at 18' C. It is only used in the form of an alcoholic solution, such as the official Spirit of Nitrous Ether {S2nritns Aetlieris Nifnm, U. S. P.), which contains about 4 pL>r cent, of pure ethyl nitrite. As pure ethyl nitrite has too low a boiling point to permit of its being conveniently or safely kept, we i)repare it in the form of a £0 X)er cent, alcoholic solution, which has a specific gravity of 0.833 at 15' C. To prepare from this the official Spirit of Nitrous Ether, it is simply necessary to mix one (1) volume of the concentrated 90 ORGANIC CHEMICAL PREPARATIONS. solution witli four (4) volumes of Deodoi-ized Alcohol. The alcohol used for tliis purpose should have a specific gravity of about 0.816 at 15° C, coiTespouding to about 9.").1 per cent, by volume of pure ethyl alcohol. In contact with diluted alcohol or water, nitrous ether is quite rapidly decomposed. Ethyl Oxalate {Oxalic Ether). (C. H.). C O.. {German : Aethyloxalat. OxalSther.) A colorless, limpid liquid, having a slightly aromatic, acidulou.s odor. Specific gravity 1.0824 at 15" C. Boiling point 185° C. Ethyl Salicylate {Salicylic Ether). C.H.-C. H.-,0:,. (Gcrinun : Aethylsalicylat.) A colorless, or faintly yellowish, aromatic li(|uid. Specific gravity 1.13-45 at 15^ C. Boiling jwint 231" to 232° C. Ethyl Yaleriauate ( Valerianic Ether). C2H5-C5H1.O,. (German : Aethylvalerianat.) A colorless, neutral liquid, having an agreeable, fruity odor. Specific gravity 0.866 at 18° C. Boiling jjoint about 135° C. Eiiealyptol {Cineol). Eiualyptol. (Gcnnan: Eucalyptol.) CioHigO. This article has received official recognition in the U. S. Pharma- copoeia of 1890, where its characters are fully and accurately described. It is the most valuable constituent of the Eucalyptus Oils, and, being a definite chemical substance, has the advantage over the latter of being of constant composition. The following characters are especially indicative of its purity: "A ccjlorless liquid, having a chai'acteristic, aromatic, and distiuctly camplioraceous odor. Specific gravity 930 at 15° C. Boiling point 176° to 177° C. It is optically inactive. AVhen exposed to a temperature some degrees below 0° C, or placed in a freezing mixture, it solidifies to a mass of colorless, needle-shaped crystals, which liquefy at — 1° C." The wide distribution of eucalyptol or cineol will be indicated by the following enumeration of the essential oils in which it has thus far been observed to occur. These are grouped according to the natiu-al orders of tlie respect- ive plants whicli afford them : ;MYRTArF..-T:. Eucalyptus globulus, E. oleosa, E. odorata, E. ro- strata, E. microcori/s, E. Bayleyana, and E. amyg- dalina. Melaleuca Leucadendron, Myrtus Cheken, and Myrtus eomiuunis. CoMPOSiT.*:. Arteuiisid paiiciflora {A. Cina). Labiat.-k. Lavandula dentata, L. Sjyica, L. stoechas, Mentha piperita, Rosmarinus officiualis. Salvia officinalis. I ORGANIC CHE:\IICAL PREPARATIONS. 91 Laurace.-e. Laurus Camphot-d, Lauriis commnin's, (hrodaphne calif om tea. Canellace^. Canella alba. ZiNGiBERACE.E. AlpUiia offlciuarnin. Ciirciniia Zcdoaria. and Ka-inp- feria rotunda. Enu'eiiol. C,« H,, 0-,or C.-, H3-^' OCH3 jOH. [Para-oxy-meta-methox y-all ji benzol.] {German: Eugenol.) This is the essential constituent of the oil of cloves, in which it occurs in amounts of about 75 to 90 i^er cent. It is also found in the oil of pimenta, oil of bay, oil of massoy bark, and in small amounts in the oils of ceylon cinnamon, sassafras, and in camphor oil. It is a monatomic phenol. When freshly distilled it forms a colorless liquid, having an odor and taste strongly resembling that of the oil of cloves. Specific gravity 1.072 at lo' C. Boiling point 2o3' to 254° C. (mercurial column entirely in the vapor). It should form a clear solution with a one or two per cent, solution of potassiuna hydrate. Eugenol may be used for the same purposes as the oil of cloves, and. being a body of definite and constant composition, its purity may readily be determined by the above mentioned characters. Formic Ether, sec Ethyl Formate. Geraiiiol. c,„h,.-oh. (GciiiKin: Geraniol.) Tliis is the chief constituent of the true Geranium Oils and of the so-called Turkish Geranium or Palmarosa Oil. It has also quite recently been shown to represent the chief constituent of the liquid portion of the Oil of Rose (see the latter), and it occvirs in smaller amounts in the Oil of Citronella, Oil of Lavender Flowers, and the Oil of Eucalypdus macnlata, var. citriodora. Geraniol is chemically a monatomic alcohol. In a perfectly pure state, as now prepared by us, it forms a colorless li(|uid, having a frag- rant, rose-like odor. Specific gravity 0.883 to 0.885 at 15° C. Boiling point 230' C. Optically inactive. One part of geraniol yields with 12 to 15 times its volume of 50 per cent, alcohol a perfectly clear solution. Geraniol is very readily oxidized, even by exposure to the air, and its specific gravity and boiling point become thereby increased. It is tlierefore important that it should be kept in well- stoppered bottles, which should be as completely filled as possible, and stored in a cool place. By oxidation with a chromic acid mixture it is converted into citral, and with potassium permanganate it yields iso-valerianic acid. Dehydrating agents convert it into teri^enes (dipentene and terjiinene). Pure geraniol promises to be of great value to the perfumer and soapmaker. It has a much finer odor than tlie geranium oils, and 92 ORGANIC CHEMICAL PREPARATIONS. it is not improbaljle that in sonie cases it may l)e capable even <>{ replacing rose oil itself (see Schininiel & Co. 's Bericht, April, 1894, pp. 48 and 03). Gerauyl Acetate. c.oHiT-CaH.o,. (Germnn : Geranylacetat.) This is a colorless liquid, liaving an odor resenil)ling tluit of oil of lavender flowers, but still finer. It lK)ils at 111 to 115' C, under a i3res.sxire of about 10 Mm. It is of great practical value in perfumery. Geraiiyl Formate. c.„H:,-cho.. (Gcnnau : Goranylformiat.) This conijwund has a characteristic, agreeable odor. It boils at 104" to 105° C, under a jn-essure of about 10 Mm. O Heleiiill {Alanto-lactone). C14H00C0. (German: Helenin.) A crj-stalline substance obtained from Elecampane, the root of Inula Helenixm Linne. It fuses at 76' C. It is sparingly soluble in water, but readily soluble in alcohol and in ether. When heated with sohitions of the alkalies it is converted into the corresponding salt of alantic acid, CjiHooCOOH. (See also Oil of Elecampane, Part II.) It is said to be efhcacious in the treatment of cholera, in whooping cough with children, and to possess valuable antiseptic properties. Heliotropill {Plperonal) . C. H„ O3 or CH., < % > C„ H.-COH. [Mcthyk'iie ether of pi-otocatechuic aldehyde] {Gi-rman : Hcliotropin.) This especially fine substance i^ossesses in a high degree the ex- quisite odor of tlie Heliotrope flower {HeJioivopium perui'ianum Linne), and has therefore become an estal)lished and most valuable article in perfumery. It forms small, colorless, shining crystals, which fuse at 37° C, and at higher temperatures volatilize without leaving any residue. It is very sparingly soluble in water, but readilj' soluble in alcohol, ether, vaseline and glycerin. It is unfavorably influenced Iw heat and light, and shoidd therefore be kept in a cool, dark place, or, in warm climates, preserved in alcoholic solution. It is used for imparting the delightfid heliotrope odor to perfumes, soaps, and pomades, and is often advantageously combined with cumarin or various essential oils, such as lavender, geranium, sandal- wood and i^etit grains. Linalool. c.oH„-oh. (Girmaii : Linalool.) This is the essential and fragrant constituent of the Oil of Linaloe see the latter. Part II), and has also been found, either in the free I ORGANIC CHEMICAL PREPARATIONS. 93 state or in the form of esters, in the oils of lavender, bergamot, petit (Crains, and coriander. A similar, if not identical body, "uerolol," lias been found in the oil of neroli, and the so-called " asax-ol," occurring in the oil of Asarnm Canadense Linne (see the latter. Part II), is like- wise apparently identical with linalool. Linalool is a colorless, or nearly colorless, fragrant liquid, having the chai'acters of a monatomic alcohol. By oxidation with a chromic acid mixture it is converted into citral. Specific gravity 0.878 at 15° C. Boiling point 197"" to 198° C. It occurs in two optically different modifications, being either dextrogyrate or la?vogyrate. It forms a perfectly clear solution with 3 volumes or more of 70 per cent, alcohol (see Ber. d. deutsch. cheiu. Ges., 24, 1891, p. 207). Linalool is a highly esteemed article in perfumery. Linaloyl Acetate {Bergcmiiol). C10H17-C, H3O,. {German : Linaloylacetat.) This ester has a strong bergamot odor, and is indeed one of the principal constituents of bergamot oil. It boils at 108° to 110° C, under a pressure of about 10 Mm. It is a valuable article in perfumeiy. Linaloyl Formate. Cu,h„-cho,. {German : Linalojil'ormiat.) This ester has an odor reminding of the oils of jjetit grains and bergamot. It boils at 100° to 103° C, under a pressure of about 10 Mm. Menthol. Cu,h,„-oh. Menthol. {German: Menthol.) This article has received official recognition in the U. S. Pharma- copoeia of 1890, and in the German Pharmacopoeia, where its general physical characters and tests for purity are described. It forms "colorless, acicular or ijrismatic crystals, having a strong and pure odor of peppermint, and a warm, aromatic taste, followed by a sensation of cold, when air is drawn into the mouth. It melts at 43' C. to a colorless liquid, boils at 212° C, and volatilizes slowly at the ordinary temperature. Its alcoholic solution is neutral to litmus paper, and deviates polarized light to the left." The boiling point of pure menthol w^e find to be at 215.5° C, with the mercurial column of the thermometer entirely in the vapor, and with a barometric pressure of 758 Mm. Menthol is undoubtedly the most valuable constituent of Pej^per- mint Oil (compare the latter. Part I). Its chemical deportment indi- cates it to be a secondary alcohol, yielding by moderate oxidation with a chromic acid mixture the ketone known as menthone, CioHitO, and with organic acids it combines to form esters, such, for example, 94 ORGANIC CHEMICAL PREPARATIONS. as those below described. By the action of dehydrating agents, mentliol is converted into the hydrocarbon menthene CiuHi^., which boils at 167" C. (For some interesting papers on bodies belonging to the so-called menthol group, seeKi'emers, in Proc. A)ner. Pharm. Ahsoc, 1893, pp. 273-287; Ibidem, 1893, pp. 185-195; and Wallach, in Liebig's Annalen, 276, p. 296, and 277, p. 154.) Menthol is used medicinally for a variety of pui-poses, both internall}', extei-nally, and in the form of inhalation. Meiithji Formate. c,oH,.,-cho,. (Gcruian : ilenthylformiat.) This is the foi'mic acid ester of menthol. It congeals at 9° C, and boils at 95' C, under a pressure of about 10 Mm, Meiithyl Valerianate. c,,,h,,-c.h.o.. (German : Menthylvalenaiiiit.) This is the valerianic acid ester of menthol. It .boils at 125" to 127° C, under a pressure of about 10 Mm. Both of the above compounds may be assumed to possess medi- cinal value and interest. Methyl Beuzoate {Mobe Oil). CH.-c.HaO.. {German : Mcthylbenzoat.) A colorless, aromatic liquid, almost insoluble in water. Specific gravity 1.0950 at 15= C. Boiling point 197.5' to 199.5= C. Methyl Salicylate, see Oil of Wiutergreeii, Synthetic, Part I. Methyl Taleriauate. CH^-CsH.o,. (German : Methjivalerianat.) A colorless liquid, having an agreeable, fruitj' odor. Specific gravitj' 0.885 at 17' C. Boiling point about 116° C. Myrtol. (German : Myrtol.; This preparation is not a simple, definite substance, but consists of that portion of Oil of Myrtle (see the latter, Part II) boiling between 160° and 180 C, and is therefore a mixture of dextrogyrate pinene, cineol, and dipentene. Its medicinal properties are similar to those of the Oil of Myrtle. Neroliii I. (German: Nerolin.t This substance represents in a remarkable degree the perfume of the Oil of Neroli or Orange Flowers, and is capable of replacing the ORGANIC CHEMICAL PREPARATIONS. 95 latter in perfumes and soaps. It occurs in handsome, white, scale- like crystals, wliich are readily soluble in alcohol, and in the essential and fatty oils. It melts at 35' C, and shovild therefore be kept in a cool place. Nitrous Etlier, see Etliyl Nitrite. Oxalic Ether, see Ethyl Oxalate. Safrol. CioHu.O, or CH.C.H3-C3H5. [Methylene ether of allyl-dioxybenzol.] (German : Safrol.) This is the essential constituent of the Oil of Sassafras, and it is also contained in Camphor Oil. At ordinary temi^eratures it is a per- fectly colorless liquid, possessing in a high degree the pure aromatic odor of sassafras. Specific gravity 1.108 at 15' C. Boiling point 232^ to 233 C. It is optically inactive. At slightly reduced temperatures pure safrol forms large, monoclinic prisms, which melt at 13" C. Safrol is a definite chemical substance, of constant composition, and is now produced by our Leipsic house on a very large scale, and in the highest degree of purity. It therefore possesses many advantages over tlie Oil of Sassafras and similar mixtures, which are often merely impure fractional distillates of camphor oil. On account of its pure and highly agreeable odor it has become almost indispensable in the manufacture of soaps, etc. (Compare Oil of Sassafras, Part I, and Oil of Camphor, Part II.) Salicylic Ether, see Ethyl Salicylate. Terebene. Terebeuum. (German : Tereben.) This preparation has been oflicially recognized for the first time in the U. S. Pharmacopeia of 1890. A recent investigation, conducted in our Garfield laboratories (see PJiarm. Buiidsdiau, N. Y., January, 1894), has shown, however, that the commonly accepted definition and description of this compound should be slightly modified. As prepared by us, according to the process originally suggested by Deville, it has the following characters: A colorless liquid, having an agreeable, somewhat aromatic odor, reminding of cymol. Specific gravity about 0.855 at 15° C. Boiling point between 170° and 185° C. It is perfect hj inactive optically. It consists chiefly of the hydrocarbons dipentene and terpinene, with some cymol and camphene. On account of its tendency to become resinified on exposure to light and air, it should be kept in well-stoppered bottles, in a cool place. A particularly important test for the purity of this preparation is its optical inactivit}', as the presence of unaltered oil of turj^entine can thus easily be detected. 96 ORGANIC CHEMICAL PREPARATIONS. Terebene is regarded as a valuable stimulant expectorant, especially in that form of chronic bronchitis known as winter cough. It is also stated to be an active antiseptic and germicide. Terpiii Hydrate. c.„h,.(OH).+h.o Terpini Hydras. (German : Terpinhydrat.) This preparation, like the preceding, has been officiallj^ recognized for the first time in the U. 8. Pharmacf>pfeia of 1890. where its characters are fully described. Terpiiieol. C:„h„-oh. (German : Tei-jjineol.) This is a definite chemical body, having the characters of a monatomic alcohol, and was first brought into commerce by Messrs. Schimmel & Co., of Leipsic. It is a colorless, thick liquid, having a pleasant odor, strongly resembling that of fresh lilac flowers {Syringa vulgaris Linne), and has therefore also received the name of " lilacine." Its specific gravity is 0.940 at 15° C. Boiling jjoint 216° to 218° C. It is readily soluble in alcohol, ether, vaseline, and the iatij oils. Terpineol is a highly esteemed article in the manufacture of fine perfumes or floral extracts, especially the so-called "lilac," and is also used for perfuming toilet soaps. (For some interesting scientific investigations relating to ter[)ineol and its derivatives, see Wallach, in lAebig's Annalen, 275, pp. 103, 151, 277, p. 105; and Baeyer, in Bor. d. deutsch. chem. Gen., 2G, p. 826, 27, p. 443.) Thymol. c,„ H14 o or c. h. — cfn, Thymol. \()H []\[ethyl-propyl phenol.] (German: Thymol.) This body is recognized by Ijoth the United States and German Phar- macopoeias, where its characters and tests for purity are fully described. It occurs in the essential oils of Tliymus vidgaris Linne, Jlonarda punctida Linne (Nat. Oixl. Lahiatce), and Carum Ajoican (Roxburgh) Bentham et Hooker (Nat. Ord. UmheUifene). Thymol forms "large, colorless, translucent crj'stals of the hexa- gonal system, having an aromatic, thyme-like odor, and a pungent, 'aromatic taste, with a very slight caustic effect upon the lips. Its specific gravity, as a solid, is 1.069 at 15° C, but when liquefied by fusion it is lighter than water. It melts at 50° to 51° C, remaining liquid at considerably lower temperatures. It is soluble in about 1200 parts of water at 15^ C, and in less than its own weight of alcohol, ether, or chloroform. Its alcoholic solution is optically inactive. " Tln-mol possesses valuable antiseptic properties. Valerianic Ether, see Ethyl Yalerianate. THIS BOOK IS DUE ON THE LAST DATE STAMPED BELOW AN INITIAL FINE OF 25 CENTS WILL BE ASSESSED FOR FAILURE TO RETURN THIS BOOK ON THE DATE DUE. THE PENALTY WILL INCREASE TO SO CENTS ON THE FOURTH DAY AND TO $1.00 ON THE SEVENTH DAY OVERDUE. ir\i B m4 ^^^ u ^m 9 193^^ Oi^'fe^^^/y!: 'Pc/p^ M l^rr^?^ ' (ItjO /^^ di^f i/P^ u JUN 1 5 1971 JUN 15 19710 7 ^•HH 1 4 1074 /—fO-TCy ^ 1969^0 ^lOOm-7,'33 '"-^ik ^