144 THE CHEMISTEY OF ESSENTIAL OILS
12 mm. = 4-4 per cent., (9) 142° to 147° at 12 mm. = 5 per cent., (10)
147° to 152° at 12 mm. = 114 per cent., (11) 152° to 157° at 12 mm.
= 17-8 per cent., (12) 157° to 162° at 12 mm. = 11-4 per cent., (13) 162°
to 172° at 12 mm. = 2'2 per cent.: residue, 14 per cent.
The first fraction had the following characters: Specific gravity
1 *1059; optical activity 0°. Combustion figures agreed with the formula
C 10 H 10 Oi{, and the solidified oil melted at 9°. This was practically pure
safrol. It was definitely identified by preparing from it specimens of
piperonal and safrol-a-nitrosite. The piperonal melted sharply at 37°,
and the nitrosite at 130° to 131°. Fractions 2 and 3 consisted chiefly of
safrol also.
Myristicin was identified in the higher boiling fractions by dissolving
a small quantity in petroleum ether and adding bromine, also dissolved
in petroleum ether to slight excess. A heavy oily layer separated, which
afterwards solidified. By recrystallisation from methyl alcohol, crystals
were obtained of the formula C 1 1H 10 O 3 Br 4 , and melting at 128°. This
agrees with the characters of dibromomyristicin dibromide, and this was
confirmed by converting it into dibromomyristicin. This was achieved
by dissolving it in glacial acetic acid and adding zinc dust. After wash-
ing away the acetic acid, the residue was extracted with ether, and the
ethereal solution evaporated. The residue solidified, and was recrystal-
lised from methyl alcohol, when it was found to melt at 52°. It was,
therefore, proved that myristicin was present in the oil. Further proof
was obtained by oxidising this fraction of the oil, when myristinic alde-
hyde and myristinic acid were obtained.
Myristicin, however, only contains one methoxyl group, whilst the
methoxyl determination showed that more methoxyl was present than
is indicated by the amount of myristicin found. A trimethoxy com-
pound was suspected to be present, but, unfortunately, could not be
isolated in a sufficiently pure state for identification. Trimethyl-gallic
acid was found in the oxidation products, which agreed with the pres-
ence of iso-elemicin in the oil, which had first been treated with alcoholic
potash. Therefore, elemicin was probably present in the original oil.
This was confirmed by preparing the crystalline dibromide of iso-
elemicin, which melted sharply at 88° to 89°. Elemicin, which was
isolated from oil of elemi by Semmler, has the formula C 6 H 2 (OCHS)«
(CH 2. CH : CH 2 ).
OIL OF SASSAFKAS.Oil of sassafras is distilled from the root of Sassafras officinale
(Laurus sassafras of Linnaeus), a native of North America. The tree
is one of the most widely distributed in the continent, being found in
Canada, in all the States east of the prairies beyond the Mississippi, and
in Mexico. In Canada it seldom exceeds 30 ft. in height, but in the
south, especially in Virginia and the Carolinas, it reaches nearly 100 ft.
in height. The root bark (except the outer layers) is the most aromatic
portion of the plant, and from this, as well as the wood, the essential oil
is distilled. The roots may be dug out at any season, but those dug
when the sap is not rising yield the highest percentage of oil. Some of
the large roots weigh nearly half a ton, but the smaller roots are most
valued on account of their higher yield of oil, The typical distilleries in
the neighbourhood of Baltimore use wooden tanks as stills. These are