RUTACEvE 453Fraction 1, at atmospheric pressure, boiled at 175° to 176° and yielded
with bromine a tetrabromide melting at 125°. It consisted of almost pure
dipentene.
Fractions 3 to 5 were united and again fractionated, yielding a liquid
having the properties of d-linalol. Its specific gravity was 0868, optical
rotation + 14° 20', and boiling-point 78° at 14 mm. pressure. The
identity of this body with linalol was proved by its conversion into citral
and Z-terpineol.
The citral obtained in the oxidation with a chromic acid mixture
yielded the characteristic naphtocinchoninic acid with a melting-point
between 197° and 200°. Treatment with formic acid produced Z-terpineol
with a melting-point of 35°. An alcoholic solution containing 36 per
cent, of this terpineol had the specific rotatory power [ao] = - 10° 14' at
18°. Treatment with carbanil yielded terpinylphenylurethane melting at
112° to 113°.
It is thus proved that d-linalol, previously found only in coriander oil,
is also a constituent of wartara oil.
The oil from Xanthoxylum senegalense (Fagara Xanthoxyloides) has
been examined by Priess, and found to have the following characters :—
Specific gravity 0-9229
„ rotation - 1° 20'
Acid value 2-19
Ester,,...........58-5
The oil contains methyl-nonyl-ketone, and, probably, decyl aldehyde-
Dipentene, linalol, a sesquiterpene, esters, and the lactone xanthotoxin
were also isolated from the oil.
Thorns, who isolated this body, considered it to be a coumarin-like
compound, related to citraptene. His latest investigations
l
have con-
firmed the correctness of this supposition. He obtained a solid substance
(melting-point 128°) which was separated by repeated recrystallisation
into two bodies, xanthotoxin (melting-point 145° to 146°) and bergaptene
(melting-point 190° to 191°), the latter a constituent of bergamot oil. The
two bodies are isomeric, but bergaptene is a phloro-glucinol derivative,
whereas xanthotoxin is derived from pyrogallol.
From a botanical point of view the occurrence of. xanthotoxin and
bergaptene in this oil, and of bergaptene in that of bergamot oil, is in-
teresting, for the two plants are closely related, belonging to subdivisions
of the same botanical family,
The following formulae indicate the relationships of the two bodies :—
OCH 3 OCH 3
-YY •co HO/XCH•.CH
OHCH [ j -O\ yO. CO
Xanthotoxin. Bergaptene.
OIL OF EVODIA SIMPLEX.
An oil distilled in E6union from Evodia simplex has been examined
by Schimmel & Go.,^2 who found it to have the following characters :—
Specific gravity......0-9737
Optical rotation - 13° 4'
Acid value .......... 2-1
Ester ,, 16-4
,, ,, (after acetylation) ....... 63*3
Berichte, 44 (1911), 3325.^2 Bericht, October, 1906, 83.