30 REPORT OF SCHIMMEL & Co. OCTOBER 1914 | APRIL 1915. 3 
Lime Oil. The Imperial Institute of London*) reports on a lime oil produced by 
distillation in the Fiji islands. The oil was of light yellow colour and possessed the 
characteristic odour of the product as distilled in the West Indies. Specific gravity 
and rotation also were in accordance with West Indian-oil: diso 0,868; apo10 + 37°6’, 
Oil from Lophanthus rugosus. On page 73 of our Report October 1913 we des- 
cribed the oil from Lophanthus anisatus (N. O. Labiate). P. de-Vilmorin and F. Levallois *) 
now report on the oil of another Lophanthus species, namely L. rugosus, Fisch. et Mey. 
The genus Lophanthus comprises 6 to 8 species which occur in northern America 
and eastern Asia. Whereas L. anisatus originates from northern America, Z. rugosus 
is a plant which grows wild, and is also cultivated, in eastern Asia, and which may 
attain a height of 1,20 m. (40 to 50 inches). The yield of oil amounts to about 0,23 p.c. 
(calculated for fresh herb?). The inflorescences contain a little more oil, up to 0,5 p.c. 
The oil is an amber-coloured liquid, soluble in every proportion of 95-p.c. alcohol, 
in 1,2 vol. of 90 p.c., in 4,5 vols. of 85 p.c. and in 23 vols. of 70 p.c. alcohol. d 0,962 
to 0,967; [«]p + 4,89 to + 6,19°; sap. v. 3,7; sap. v. after acetylation 7,4. The oil reacts 7 
slightly with bisulphite. About 8 p.c. boil from 60 to 63° (10 mm.), 2 p.c. from 63 to | 
90° (10 mm.), 86 p.c. from 90 to 94° (10 mm.) and about 4 p.c. above 100°, with 
partial decomposition. Methylchavicol appears to be the chief constituent, it was | 
characterized by being converted into anethole, m. p. abt. 20°. The fractions of the 
b. p. about 60° (10 mm.) contain presumably d-limonene: b. p. 174°; d=> 0,8494; 
[<]p + 106,8°; tetrabromide, m. p. 104°; nitrosochloride, m. p. 103 and 105° respectively. 
When the nitrosochloride was purified, a body of the m. p. 154° was obtained, a 
corresponding hydrocarbon of which the authors have not yet ascertained. 
Mastic Oil. For some considerable time d-pinene*) had been suspected in 
mastic oil. In order to settle the question the fractions that passed over first in the 
process of distillation were collected by us separately and examined very closely. 
They had the following properties: b. p. 156 to 170°; disco 0,8599; ap -+ 38°57’; npsoo 1,46925. 
The peculiar balsamic odour pointed to the presence of pinene and phellandrene. 
The oil, however, did not yield any phellandrene reaction when treated with nitrous 
acid. A fraction of the b. p. of 156 to 157° (dis0 0,8615; a) + 39° 14’) gave an infini- 
tesimal precipitate of a nitrosochloride, m. p. 106° (benzylamine base, m. p. 123 to 124°). ~ 
The slight yield of nitrosochloride from such a strongly active pinene fraction made 
the simultaneous presence of active and inactive «-pinene probable. In order to 
establish proof of both bodies an attempt was made to obtain the corresponding pinonic 
acids by means of permanganate oxidation. In what passed over first of the resulting 
acid mixture, traces of an acid, melting indifferently between 95 and 98°, could be 
proved, which was perhaps identical with pinonic acid obtainable from inactive pinene, 
and melting at 104°. Besides this, an acid of the m. p. 183 to 185° was also isolated. 
From the main fraction of the acid mixture, inspite of inoculation with inactive pinonic 
acid, m.p. 104°, crystals of the active acid only, melting at about 70°, could be 
obtained: [«]p +-90,15° (8,8717 p.c. solution in chloroform); semicarbazone, m. p. 204°. 
Even a close examination of the mother-liquors yielded no acids melting at 104°. 
From the semicarbazone, produced therefrom with a melting point of 195 to 200°, a 
semicarbazone melting at 190 to 191° was isolated, which proves that the crude 
1) Bull. Imp. Inst. 12 (1914), 227. — %) Bull. Soc. chim. IV. 15 (1914), 342. — 8) Gildemeister and 
Hoffmann, The Volatile Oils, 1st Ed., p. 496. a 
