Chemistry of Essential Oils

278 THE CHEMISTRY OF ESSENTIAL OILS

Per Cent,

Benzyl acetate 65

Linalyl ,, 7-6

Benzyl alcohol 6

Linalol 155

Indol 2-5

Jasmone ............ 3

Methyl anthranilate 0*5

Schimmel & Co. could find no jasmal in the oil, and more recently

Hessel has found small quantities of indol, methyl anthranilate, and a

ketone which he terms jasmone, a sweet-smelling oil of specific gravity

0-945 and boiling at 257° to 258°.

Jasmone forms an oxime melting at 45° and a semicarbazone melt-

ing at 201° to 204°. Elze

2

has also isolated geraniol and para-cresol

from jasmin oil.

There is another compound which can easily be prepared artificially

which has a distinct jasmin odour. The styrolene compounds are, as a

group, remarkable in taat they often possess floral odours. Thus, the

alpha-substitution products of styrolene C 6 H 5. CH : CH2, such as brom-

styrolene C 6 H 5. CH : CHBr, have usually a distinct hyacinth-like odour.

Styrolene alcohol C 6 H 5. CH(OH)CH 2 OH is identical with phenyl-

glycol, the basis of the above-mentioned French patent; whilst second-

ary styrolyl acetate C 6 H 5. CH(O. CO. CH 3 )CH 3 has itself a marked

odour of jasmin. This body can be prepared by the action of bromine

on boiling ethyl-benzene. The resulting bromide is heated with silver

acetate and glacial acetic acid, yielding styrolyl acetate.

Artificial oil of jasmin compounded on the lines of the above-

mentioned facts is now a regular article of commerce. It closely

resembles the natural perfume, except that it is less delicate, and is

well adapted for high-class toilet perfumery.

ERICACEAE.

OLL OF WINTERGREEN.

This oil is one of those which is so closely imitated by other oils
that the commercial article is very seldom the true oil at all. Genuine
wintergreen oil is the product of distillation of the leaves of Gaultheria
procumbens; " commercial" wintergreen oil is almost invariably the
product of distillation of the bark of Betula lenta, one of the Betulacea;
or an artificial synthetic oil, methyl salicylate. Gaultheria procumbens
is a plant of North America, known as the tea berry or partridge berry.
The leaves are gathered and distilled in primitive apparatus, either
ordinary whisky stills, or stills composed of wooden tubs with copper
bottoms. The resulting oil, which is yielded to the extent of -5 to 1
per cent., has a specific gravity 1180 to 1193, and is faintly laevo-
rotary (under - 1°). It distils between 218
°
to 221°. Its refractive
index is about 1*5350. The bark of Betula lenta, the sweet birch, yields-
about the same quantity of an oil of so exactly similar a nature that it is
now sold as oil of wintergreen to the almost entire exclusion of the true
Gaultheria oil. The oil is the product of decomposition of the glucoside

(^1) Bericht, 32 (1899), 2611; 33 (1900), 1585; 34 (1901), 291, 2916 ; 37 (1904), 1457.
2
Chem. Zeit., 34 (1910), 912.