24 REPORT OF SCHIMMEL § Co. OCTOBER 1914/APRIL 1915. 
add iodine. For instance, 0,2 g. of pinene used up 13,7 cc. of one-tenth-normal iodide 
solution, that is to say, about as much as Fromm and Fluck indicate for 0,2155 g. 
cineol. Seeing that in eucalyptus and cajuput oils we have to deal with such mixtures, 
this method is not adapted for the quantitative determination of cineol in these oils. 
Presumably the combination just described is really the double combination 
Cio His Ole + CioHisOHI, which might be termed cineol di-iodide-hydriodide. According 
to Fromm and Fluck it is not impossible, that the cineol-di-iodide described by Wallach 
and Brass does not exist at all, and that these authors may have had to deal with 
an impure cineol di-iodide-hydriodide. 
There were also obtained from galangal oil: 1 to 2 p.c. of a body of the b. p. 208 
to 210°. This new substance has the empirical composition CioHigO. Nothing 
further was ascertained concerning the manner of the linking of the oxygen. A ses- 
quiterpene was also isolated from the oil, which is diolefinic, adding 4 atoms of 
bromine and boiling at 138 to 140° (12 to 15 mm.). It is not identical with the 
sesquiterpene found in this oil by Schindelmeiser; no addition product is obtained 
with hydrogen chloride. A. second sesquiterpene found in the oil yields a hydro- 
chloride Ci;He:-2HCI, of the same melting point as cadinene hydrochloride, but on 
being mixed with the latter it shows a perceptible lowering of the melting point (by 
about 10°). From the high-boiling parts white needle-like crystals are separated 
occasionally after prolonged standing; these may be purified from hot alcohol. Their 
melting point lies at 167°, and they correspond with the formula of a sesquiterpene 
hydrate Cis He, O. 
According to Horst, eugenol is supposed to be contained in the oil to the extent 
of 25 p.c, but the authors have failed to establish its presence. 
Galbanum Oil. About the composition of this oil little had been published so 
far; all that was known was that it contained d-«-pinene and cadinene. An examination 
carried out a short time ago by F. W. Semmler and K. G. Jonas) revealed a few further 
constituents. The oil analysed had the following properties: b. p. 55 to 195° (15 mm.); 
de50 0,9353; &po50 + 8°; Npws0 1,49395. In the low-boiling parts «-pinene (nitrosochloride, 
m. p. 107 to 108°) was present, as well as @-pinene (nopinic acid, m. p. 128°). On 
testing for camphene, a mixture of the optically active terpineols, m. p. 35 and 32°, 
was obtained, instead of isoborneol. The formation of these bodies is explained by 
an addition of water to pinene, i.e. 8-pinene. Myrcene was easily established by con- 
version to camphorene and by production of the «-camphorene tetrahydrochloride’). 
A fraction of the b. p. 100 to 120° (15 mm.) (doo 0,9504; &px20 + 10°; npz20 1,49181) 
possessed in a particularly strong degree the peculiar bitter-aromatic odour of 
galbanum oil and contained a body CyHi.O; b. p. 105 to 115° (15 mm.); dao 0,951; 
ap + 6°; np 1,4918. Possibly we have here to deal with a ketone, which is very easily 
enolizable. On oxidation the fraction yielded a ketonic acid CioHigQO3, which, when 
treated with alkaline solution of bromine, was converted into a dicarboxylic acid CyHi4O.. 
A fraction obtained by repeated distillation over sodium had the following figures: 
b. p. 132 to 138° (10 mm.); dio 0,9282; epis0 + 339; Npiwo 1,50526. On the addition of 
hydrochloric acid gas it furnished 7/-cadinene dihydrochloride. According to Semmler 
and Jonas it is, however, an open question as to whether in this dextro-rotatory 
fraction /-cadinene is actually present, the laevo-rotation of which is covered by a 
strongly dextro-rotatory body, or whether the dextro-rotatory sesquiterpene contained 
1) Berl. Berichte 47 (1914), 2068. — %) Comp. Report October 19138, 35. 
