Cayenne-Linaloeol. - Essence de Bois de Rose femelle. - Essence d'Azelia.
Origin. The linaloe wood of French Guiana, or Cayenne linaloe wood is known as Likari kanali by the natives and as Bois de rose male by the French colonists. It is also known as bois de rose, sarsaffras, bois de rose femelie, bois jaune, bois de citron de Cayenne, cedre jaune, or copahu. No doubt, these names are applied to aromatic woods of different botanical origin.
The strongly fragrant wood, which upon distillation yields the Cayenne linaloe oil, is hard and heavy, and cleaves readily.
1) Report of Schimmel & Co. October 1894, 69; October 1906, 59.
2) Ibidem October 1906, 59.
3) U. S. Dep. of Agriculture, Bureau of Plant Industry, Bull. No. 235 (1912), p. 29.
The fresh surface is yellow, the older surfaces are reddish. From Cayenne it is exported in the shape of cord wood from which the bark has not been removed. The size of the pieces admits the inference of large trees.
The plant from which the Cayenne linaloe wood is obtained has not been definitely ascertained. According to J. Moller1) it may be assumed with a fair degree of probability that Ocotea caudata, Mez. (Licaria guianensis, Aubl.), a tree belonging to the family Lauraceae, is the source.
E. M. Holmes2) collected the statements of former authors, some of which are rather contradictory. He is of the opinion that the bois de rose femelle is derived from Protium (Icica) altissimum, March (family Burseracese), and not, as stated by Moller, from Ocotea caudata. The wood of Ocotea caudata (Licaria guianensis of Aublet, PI antes de Guiane Frangaise, p. 313) is known in Cayenne as Bois de rose male. The natives designate the young trees as Licari kanali, but regard the older specimens as a different plant which they call sarsaffras. From the account of Holmes, however, it does not appear which of the two woods yields the oil of commerce.
At the present time the large forests between the Maroni and Oyapock Rivers, in French Guiana, yield the bulk of the wood. It is cut by negroes and carried on the back to the nearest river whence it is shipped to the coast. Originally all the wood was shipped to Europe. Later, several factories were erected which distilled nothing but Cayenne linaloe oil. Nevertheless, large shipments of wood occasionally reach Europe. Frequently the best period for cutting, when the wood is richest in oil, is disregarded. Again, the wood is exposed for an unnecessarily long time to the alternating influence of sun and rain, thus causing a decrease in the oil content3). As a result the oil yield fluctuates considerably, varying between 0,6 and 1,6 p.c.4). The average yield is about 1 p.c.6).
1) Pharm. Post 29 (1896), Nos. 46 to 48. - Jahrbuch des Kgl. bot. Gartens zu Berlin 1889, 378.
2) Perfum. and Essent. Oil Record 1 (1910), 32.
3) P. Jeancard, Parfumerie moderne 5 (1911), 53.
4) E.Theulier, Rev. gen. de Chim. 3 (1900), 262.
5) Roure-Bertrand Fils, Perfum. and Essent. Oil Record 1 (1910), 33.
Properties. The oil is a liquid with the pleasant odor of linalool d16o0,870 to 0,880; aD - 10 to - - 19°; nD20o1,461 to 1,463; A.V. up to 1,3; E.V. up to 6,3. The alcohol content, computed as C10H18O and determined by acetylating for 7 hrs. in xylene solution (1 to 5), was 90 to 97 p. c. The oil is soluble in 1,5 to 2 vol. or more of 70 p.c. alcohol, and in about 4 vol. or more of 60 p.c. alcohol.
Composition. Cayenne linaloe oil contains more than 80 p.c. of \-linalool. This alcohol was at first found by H.Morin1) who called it licareol. P. Barbier2) at first regarded linalool and licareol as two distinct alcohols, but later became convinced of their identity3). According to Theulier4), Cayenne linaloe oil differs from the Mexican by the absence of methyl heptenone, terpineol and geraniol. However, Schimmel & Co.5) found in the saponified oil about 5 p.c. of terpineol and about 1 p.c. geraniol (m. p. of diphenylurethane 80 to 81,5°). According to Roure-Bertrand Fils6) methylheptenone as well as nerol (about 1,2 p.c.) are present.
Of less importance are cineol (m. p. of iodol derivative 110 to 1110)7) and dipentene (m.p. of tetrabromide 124 to 125°, of dihydrochloride 47 to 48°)7) which occur in the lower fractions. The aqueous distillate contains furfurol (b. p. 159 to 161°; m.p. of phenylhydrazone 96 to 98°, of semicarbazone 196°)7), and an aldehyde, presumably isovaleric aldehyde"), which boils between 90 and 95° and produces irritation and coughing.
The lower fractions appear to contain also an aliphatic terpene. Its isolation by fractionation was not possible. When acted upon by glacial acetic acid -bsulphuric acid, about 10 p.c. of ester was obtained. The alcohol obtained upon saponification boiled at 210 to 215°; d15o 0,915. It resinified readily and its odor reminded one of linalool and terpineol. Inasmuch as the fraction used for the hydration, viz., 168 to 170°, yielded no reactions for sabinene, camphene, fenchene or pinene, it may be assumed that the alcohol owes its origin to an aliphatic terpene1).
1) Compt. rend. 92 (1881), 998 and 94 (1882), 733. - Ann. de Chim. et Phys. V. 25 (1882), 427.
2) Comp. rend. 114 (1892), 674 and 116 (1893), 883.
3) Ibidem 121 (1895), 168.
4) Rev. gen. de Chim. 3 (1900), 262.
5) Report of Schimmel & Co. April 1909, 68.
6) Berichte von Roure-Bertrand Fils October 1909, 45.
7) Report of Schimmel & Co. April 1912, 90.
Upon treating the linalool fraction with acetic acid anhydride, Barbier2) obtained products that had the odor of dimethyl-heptenyl acetate and hence assumed the presence of dimethyl-heptenol in the oil. Schimmel & Co.8), however, were of opinion that Barbier's alcohol was methylheptenol and that it should probably be regarded as a decomposition product of linalool. Later they were able to demonstrate4) clearly that small amounts of methylheptenol were contained in the lower fractions. The fraction examined had d15o0,8655 and aD - 11°40'. The alcohol, isolated by means of the acid phthalate, yielded upon oxidation methylheptenone, which was characterized by its semicarbazone melting at 137 to 138°.