62 REPORT OF SCHIMMEL & Co. APRIL 1914. 
Fennel Oil. In our last Report we described the outlook of the fennel market 
as favourable, because as a matter of fact several reports had been received which 
agreed in forecasting a plentiful output. The further development of affairs, however, 
has brought a tremendous disappointment, for whereas on the one hand the final 
result in the Russian producing districts had been over-estimated, it was further dis- 
covered that the oil-content of the new season’s fennel was surprisingly small. As 
the weather at the ripening was favourable, the above deficiency can only have been 
caused by the unfavourable climatic conditions of the summer, during the period of 
the development and flowering of the plants. The samples examined by us showed 
a shortage in oil-content of 25 p.c. as compared with normal years, although the 
appearance of the fennel itself was not bad. Naturally, this unfavourable result soon 
made itself felt in increased prices of all classes of fennel oil, and those who, like 
ourselves, have to supply a large number of important and regular buyers in the 
confectionery trade were compelled to handle their stocks with economy. As practi- 
cally no fennel has been offering lately, and as the Galician manufacturers of crude 
fennel oil are also extremely reserved in making offers, the fennel oil prices remain 
very firm, and in the course of the summer may well attain a level approaching that 
of anethol and leaving scarcely any advantage compared with the latter. In any case, 
fennel oil is one of the few articles in our branch of trade for which on this occasion 
we are able to predict higher prices. 
Frankincense Oil. The frankincense oils (olibanum oils) found in commerce at 
the present time differ from those that have been examined by us in the past?) in 
being dextrorotatory. The rotation of the earlier oils ranged from e —11 to — 17°, 
but latterly samples have come into our hands which showed @p + 17° to + 29° 41’; the 
sp.gr., however, was the same as before. We were interested in discovering whether 
this difference in optical rotation was attended by any change in the composition of 
the oil. Our investigation was restricted to the terpene fractions of the oil, seeing 
that the non-terpenes had only quite recently been investigated by Fromm. 
Gildemeister and Hoffmann, in The Volatile Oils 18‘ Ed., p. 590, name pinene, dipentene 
and phellandrene as constituents of olibanum oil. Pinene has been isolated from the 
oil by Wallach”), who showed it to be identical with Kurbatov’s olibene. Wallach 
also found that the fraction boiling between 177 and 179° contained dipentene. The 
presence of phellandrene was established by Schimmel 8 Co. by the nitrite-test, in 
which connection it is a noteworthy fact that the oil, even before fractionation, 
responded to the phellandrene-test. 
The oil now examined by us had the following constants: dis0 0,8775, %p + 19° 18’, 
Np»01,47245, acid v. 1,8, ester v. 7,5, ester v. after acet. 106,0, soluble in up to 2 vols 
of 90 p.c. alcohol, the solution being clear at first, and turning turbid after 2 vols. Of 
the terpenes, 92 p.c. boiled between 156 and 161°, about 5p.c. between 161 and 163°, 
and about 4 p.c. between 163 and 181°. In the fractions boiling between 156 and 
157° (dis0 0,862 to 0,863; «) + 30°58’) we established the presence of i- and d-«-pinene 
from the nitrosochloride and the nitrol piperidide (m.p.118°), as well as by oxidation 
into pinonic acid (b.p.170 to 175° at 7mm.; m.p. of the active acid 69 to 70°; of 
the inactive acid 104°). The presence of camphene in all the fractions boiling between 
158 and 164° was established by conversion into isoborneol, m.p. 210 to 211°. Dipentene 
1) Gildemeister and Hoffmann, the Volatile oils. 1st Ed. p. 489. — 7%) Liebigs Annalen 252 (1889), 100; 
Bericht October 1889, 37. : ’ 
