— 30 — 
characterised by the melting point of its phenylhydrazone. The last- 
named body can also be very readily identified by the semicarbazone, 
which, being scarcely soluble in water, is precipitated already from a 
dilute aqueous solution by semicarbazide acetate. It is obtained in 
this manner in the form of brilliant white laminae which turn slightly 
yellow when kept, especially when exposed to the light. The semi- 
carbazone melts at 197° with decomposition. 
Dill Oil. From Spain we received a sample of dill oil which 
had been distilled exclusively from the dill plant, and which differed 
in its properties in a marked degreee from normal dill oil. Its physical 
constants were as follows: d^^o 0,9282, -|- 45° 47', ^^20" ^A9^3^') 
it was insoluble in 80 per cent, alcohol, but formed a clear solution 
with about 5 volumes of 90 per cent, alcohol. Judged by the odour, the 
oil appeared to have a large phellandrene-content; this supposition 
was soon confirmed, for when the oil was tested for phellandrene in 
the usual manner, it gave an exceptionally strong reaction. A trial 
to determine the carvone-content by titration with hydroxylamine 
hydrochloride, showed that it amounted only to about 16 per cent. 
When fractionated in vacuo, by far the greater part of the oil, 
(four-fifths) passed over at the boiling temperature of terpenes; it was 
found to be almost pure phellandrene, which perhaps still contained 
small quantities of other terpenes. Next followed a comparatively 
small intermediate fraction, which, however, had only a very faint 
odour like carvone. The boiling point of the residue was fairly high, 
and the distillate was heavier than water. As there were grounds for 
supposing that the dill oil might contain dill-apiol, which Ciamician and 
Silber have found in the oil from East Indian dill, this portion was 
repeatedly submitted to fractional distillation in vacuo. In this manner 
there was finally obtained an oil which had a faint yellow colour, 
and which passed over constantly between 155° and 156°, at 8 mm 
pressure. As it was only a question of proving whether this body 
actually contained dill-apiol, a small quantity of the oil was heated in 
a sealed tube for several hours to 160^ with an alcoholic solution 
of sodium ethylate. The reaction-product which separated out when 
water was added, had a slightly higher boiling point than the crude 
material, and when slowly cooled it gradually solidified into a hard 
crystalline mass, which was dried on a tile in order to remove small 
quantities of liquid matter, and was then repeatedly recrystallised from 
dilute alcohol. As was clear from the melting point 43° to 44° of 
the crystals and that of their product of bromination, it was actually 
a question of dill-isoapiol. 
When the portion containing apiol was distilled, there remained 
in the flask a mass with a very high boiling point, which solidified 
