— 75 — 
was lower than that of normal Paraguay petitgrain oil. It is specially 
worthy of note that the oil contained only traces of methyl ester of an- 
thranilic acid. When the oil was fractionated in vacuo, the individual 
fractions showed a constantly increasing specific gravity, and, on the 
whole, an increasing dextrorotation. In the first fraction, rich in ter- 
pene, the authors were able to detect l-pinene and dipentene, whilst 
the last consisted chiefly of geranyl acetate. From intermediate fractions 
linalool and geraniol were obtained in the pure state, — the latter in 
larger quantity than the former, — two other intermediate fractions 
had a strong odour like terpineol, but it was not found possible to obtain 
this body in the solid state. 
Pimento Oil. Up to the present, eugenol and a not further 
identified sesquiterpene had been detected in oil of pimenta^). An 
examination made by us has enriched our knownledge of this oil with 
a few constituents of which we give the following details. 
We worked up i kilo of the first runnings of a distillation, which 
had the following constants: d-^go =0,9715; aj^= — i i°3o'(ioomm). 
On shaking the oil with soda liquor, acid constituents were ab- 
stracted from it, and the oil not combined with soda liquor (about 
500 gm.) was fractionated in vacuo. 
Cineol. The lowest boiling portions (boiling point 40° to 50^ at 
5 mm pressure) had a pronounced cineol- like odour. After destroying 
any terpenes and other readily oxidisable substances which might be 
present, by treatment with 3^/^ permanganate solution, the remaining 
oil was driven off with steam and distilled at ordinary pressure. Be- 
tween 170° and 180° about 2 gm. passed over, which were oxidised with 
permanganate (according to Wallach and Gildemeister's method 2) 
into cineolic acid of the melting point 202° to 203°. A further proof 
of the presence of cineol was supplied by its additional combination 
with iodol of the melting point 112°. 
1- Phellandrene. The slightly higher boiling portions (50° to 60° 
at 5 mm pressure) had the specific gravity 0,8619 I5°> 
rotatory power — 36^36' (100 mm). With nitrous acid they formed 
after a short time a dense flocculent precipitate, which in the crude 
state melted at about 100^, and after having been twice recrystallised 
from acetic ether at 119° to 120°; by these means it was identified 
as phellandrene nitrite. The nitrite melting at 102° to 104° was not 
observed in this examination. As the nitrite showed the specific ro- 
tatory power in io^/q chloroform solution [a]jy = -[-95°, the phellan- 
drene itself is laevorotatory. 
^) Bonastre, Journ. de Pharm. 13 (1827), 466. — Oeser, Liebig's Annalen 
131 (1864), 277. 
2) Liebig's Annalen 246 (1888), 268. 
