BUESEKACE^l4 465resin after no more oil passes over for the purpose of obtaining a larger
yield, and the distillation is then continued. The constituents of myrrh
oil identified by him are : cuminic aldehyde, C 10 H 12 O (up to 1 per cent.),
boiling-point 116° (12 mm. pressure); oxime, melting-point 56°; semi-
carbazone, melting-point 201°.—Acids: Of these, only acetic acid and
palmitic acid (melting-point 62°) were detected with certainty. Both are
present in old oils in the free state, whilst freshly distilled myrrh oil
contains the acids as esters.—Phenols (about 1 per cent.): eugenol
l
(about 0
- 23 per cent. ; benzoyl compound, melting-point 69°), and a
small quantity m-cresol were detected.—Hydrocarbons: Fractional dis-
tillation over sodium yielded four hydrocarbons (terpenes) of the formula
C 10 H 16 (all of which, however, were not found in every oil examined), of
which three were identified; pinene (nitrosochloride, melting-point 103°;
nitrolbenzylamine and nitrolpiperidine); dipentene (tetrabromide, melt-
ing-point 124°); limonene (tetrabromide, melting-point 104°); the fourth
hydrocarbon probably belongs also to the limonene group (AO + 80°,
tetrabromide, melting-point 115°, and monohydrochloride, melting-point
6°) but could not be identified. Sesquiterpenes : probably cadinene is,
present, and a second sesquiterpene of specific gravity 0'911 at 21°, and
optical rotation + 30*4°.
Friedrichs
l
distilled an oil from picked myrrh, which had the follow-
ing characters:—
Specific gravity.
Optical rotation ....
Refractive index ....
Acid number .....
Ester ,, ...vity. 1-011- 73-8
1-5359
6-15
47-6
No eugenol could be detected, but meta-wesol was present. Cumic
and cinnamic aldehydes were also found to be present. A sesquiterpene
having the following characters was also isolated :—
Boiling-point
Specific gravity.
Optical rotation.
Refractive index
Molecular refraction
130° to 136° at 16 mm.
0-943 at 20°- 14° 12'
1-5125
64-98
To this body he assigns the name herabolene.
Traces of formic and acetic acids were also found, and a non-volatile
acid melting at 159°, and an acid of the formula C 16 H 21 O 3. COOH,
melting at 236°, which he names myrrholic acid.
Bisabol Myrrh.—The principal plant yielding this resin is probably
Commiphora erythraea.
Tucholka
2
has extracted the essential oil from a Bisabol myrrh coming
from the interior of the Somali country, by removing it from the alcoholic
solution of the resin by means of petroleum ether. The oil was purified
by steam distillation, and then had a light yellow colour, specific gravity
•8836, and optical rotation - 14° 20'. It boiled at ^20° to 270°. The
yield was 7
- 8 per cent. By means of dry hydrochloric acid gas, a crys-
talline hydrochloride was separated, which, on treatment with boiling
acetic solution of sodium acetate, set free a hydrocarbon which the above-
named investigator terms bisabolene. This hydrocarbon had a specific
gravity -8914 and boiled at 260°. The same chemist suggests the unlikely
formula C 50 H9(3O for the residual portion of the oil.
(^1) Arch, der PJwrm., 245 (1907), 427.
VOL. i.. 30
(^2) Arch. Pharm., 235, 289.