In India the fruits of Xanthoxylum acanthopodium, DC. and X. alatum, Roxb. are known as wartara4) seeds.
According to the Pharmacographia Indica of Dymock, Warden and Hooper (vol. I, p. 257) this drug has long been used as spice and medicament in the Orient. By Sanskrit writers the carpels of the fruit are named Tumburu, which means coriander. The Arabs appear first to have obtained the fruits from northern India. Ibn Sina describes it as an open-mouthed (Faghireh) berry of the size of a vetch containing a seed resembling that of the hemp. Haji-Zein el Attar, in 1368, gives a similar description of the Faghireh and mentions that the Persians call the fruit t Kababeh-i-kushadeh, i. e. open-mouthed cubeb.
Upon the distillation of the fruits of X. acanthopodium, DC, Schimmel $ Co.5), obtained approximately 2 p.c. of a volatile oil the odor of which reminded distinctly of coriander. d15o0,871 to 0,874; +5°30' to +6°31'; S. V. 27,1. With 1 vol. of 80 p.c. alcohol it formed a clear solution. When distilled under a pressure of 14 mm. the following fractions were obtained.
1) Jahresb. f. Pharm. 1887, 157 and 1888, 128.
2) Originally Evodia fraxinifolia was regarded as the parent plant of this oil.
3) Bull. Sciences Pharmacol. 18 (1911), 343.
4) The designation wartara is possibly a corruption of Fagara. Both genera Fagara and Xanthoxylum are so closely related that some botanists regard them as one genus.
5) Report of Schimmel & Co. April 1900, 49 and October 1911, 49.
Amount of distillate in cc.
65 to 70°
70 „ 80°
80 „ 90°
90 to 100°
+ 12° 39'
100 „ 130°
Under atmospheric pressure fraction 1 boiled between 175 and 176°. With bromine it afforded a good yield of a tetra-bromide that melted at 125°, hence consisted almost entirely of pure dipentene.
From fractions 3 to 5 a liquid with the properties of d-lina-lool was obtained. Its specific gravity was 0,868, its angle of rotation + 14°20', its b. p. 78° (14 mm.). The identity of the substance with linalool was proven by its conversion into citral and l-terpineol. The citral obtained upon oxidation with chromic acid mixture yielded the characteristic naphthocinchoninic acid melting at 197 to 200°. When treated with formic acid the linalool yielded l-terpineol m. p. 35° (m. p. of phenyl urethane 113°).
The highest boiling fractions occasionally congeal to long needlesl) which, after recrystallization from alcohol, melt at 36° and boil at 256° (745 mm.). This is methyl cinnamate as demonstrated by the analysis of the silver salt of the cinnamic acid isolated therefrom.