The "Illurin balsam" or African copaiba balsam, which first made its appearance in the London market, is obtained from western Africa, more particularly from the Niger countries, it is said. The botanical source has not been ascertained but the Oxystigma Mannii, Harms (Hardwickia Mannii, Oliv.) is regarded as the parent plant1).
1) Liebig's Annalen 369 (1909), 57. - Chem. Ztg. 36 (1912), 561.
2) Chemist and Druggist 77 (1910), 119.
3) Ibidem 80 (1912), 19.
4) Ibidem 128, 204.
Properties. Upon distillation the balsam yields 37 to 46,5 p.c. of oil2): d15o0,917 to 0,929; aD + 5°45' to +30°; A. V. 0,5 to 9,3; E. V. 0 to 5,6; E. V. after acetylation (1 determination) 10; soluble in 98 p.c. alcohol, but the addition of more than 2 vol. produces faint opalescence; soluble in 95 p.c. alcohol in the ratio of 1:10 with opalescence").
Composition. When passing hydrogen chloride into the oil Umney4) did not succeed in obtaining a solid chlorhydrate. Upon passing hydrogen chloride into the ethereal solution of a dextrogyrate oil, H. von Soden5) obtained a dihydrochloride that melted at 116 to 119°; aD - 3° in a 10 p.c. benzene solution. The regenerated hydrocarbon had the following properties: b. p. 274,5 to 276° (743 mm.); d 0,928; aD - 94°. These properties agree well with those of l-cadinene.
Similar results were obtained by Schimmel & Co.6). 90 p.c. of an oil prepared by themselves distilled between 267 and 276°. In a vacuum of 5,5 to 6 mm. pressure it distilled between 118 and 125°. By passing hydrogen chloride into the ethereal solution, they obtained 37,5 p.c. of a chlorhydrate that crystallized in long needles melting at 117 to 118° ([a]D - 37°27' in a 5,022 p.c. chloroform solution). The hydrocarbon, regenerated with the aid of sodium ethylate, boiled at 271 to 273° ([a]D--105°30'). The addition of hydrogen chloride again yielded the chlorhydrate melting at 117 to 118° ([a]D - 36°48' in a 4,73 p.c. chloroform solution). Whether African copaiba balsam contains /-cadinene or whether the dextrogyrate sesquiterpene is converted into a derivative of l-cadinene by the action of hydrogen chloride will have to be ascertained by further investigation. Probably the relationships are similar to those observed in connection with West Indian sandalwood oil, the dextrogyrate sesquiterpene of which was converted into l-cadinene by Deussen1) through the chlorhydrate.
1) Umney, Pharmaceutical Journ. III. 22 (1891), 449 and 24 (1893), 215. - H. Solereder, Arch, der Pharm. 246 (1908), 72. - Engler and Prantl, Die naturlichen Pflanzenfamilien, Supplement to Part II - IV, 1897, p. 195.
2) Comp. C. M. Kline, Americ. Journ. Pharm. 77 (1905), 185.
3) Observed in connection with a single oil. Report of Schimmel & Co. October 1908, 48.
4) Loc. cit.
5) Chem. Ztg. 33 (1909), 428.
6) Report of Schimmel & Co. October 1909, 46.
In the lowest fraction (b. p. 128 to 129,5° under 15 mm. pressure) of African copaiba balsam oil, E. Deussen2) proved the presence of 13 p.c. of B-caryophyllene by passing nitrous acid gas into its ethereal solution. The oil that had not been fractionated yielded 1,65 p.c. of so-called nitro-B-caryophyllene corresponding to a content of 0,87 p.c. of B-caryophyllene.