Chemistry. — “The unsaturated alcohol of the essential oil of 
freshly fermented tea-leaves.” By Prof. P. van Rompouren. 
(Communicated at the meeting of May 31, 1919). 
In 1895 in collaboration with my assistant at that time, Mr. C. E. J. 
Loumann, I investigated the ethereal oil from freshly fermented tea‘), 
a small quantity of which we were successful in preparing with 
the cooperation of several tea-planters. The yield of this ethereal 
oil is extremely small, fifteen kilograms of the fresh leaves giving 
only one c.c. 
We were able at that time to detect the presence in the oil of 
an unsaturated alcohol (b.p. 153°—155°) of the composition C,H,,0O, 
evidently a hexylene alcohol. From this by oxidation an acid could 
be obtained, smelling like rancid butter, the calcium salt of which 
gave on analysis a result which indicated the presence of butyric 
acid. Lack of material prevented us from determining whether the 
acid formed was the normal or the iso-butyric acid. Later, shortly 
before my departure from Java, | had the opportunity of obtaining 
a larger quantity of the ethereal tea-oil (about 120 ec), which 
enabled me to resume the research and to investigate more in detail 
whether by the oxidation of the unsaturated alcohol one or other 
of the butyric acids is really formed. A knowledge of the nature 
of the acid is of course of primary importance for the elucidation 
of the structure of this acid. 
After treatment with alkali in order to saponify the methyl sali- 
cylate*) (the presence of which we had demonstrated in 1896) and - 
other esters*) possibly present, the crude oil was fractionated several 
times. The largest fractions boiled between 154° and 156° and 
between 156° and 158°. These were mixed and distilled in vacuo, 
the principal fraction boiled at 75°—80° at 28—30 mm. pressure. 
The sp. gr. at 15° was 0.8465; npw 1.43756. 
Elementary analysis gave 71.17°/, C. and 12.74°/, H. The formula 
C,H,,O requires 71.91°/, C. and 12.10°/, H. 
1) Verslag omtrent den staat van ’s Lands Plantentuin te Buitenzorg for the 
year 1895, p. 119. 
*) The same for the year 1896, p. 168. 
8) The salicylic acid isolated was not odourless. The smell resembled that of 
phenyl! acetic acid. 
