194 
cadinene prepared from the hydrochloride is strongly laevo-rotatory, and_ the 
amount of cadinene hydrochloride which can be obtained from it is no greater 
than that which can be separated from the original distillate. 
The distillate from Oil of Supa absorbs oxygen when it is exposed to 
the air and it gradually becomes viscous; in a thin layer it slowly hardens ; 
a piece of muslin saturated with the oil and exposed to the action of the 
air so as to avoid evaporation showed an increase in weight of over 10 
per cent in three weeks. This absorption is accompanied by a slight 
darkening in color. When a current of air is drawn through the oil at 
200°, oxygen is very rapidly absorbed and the product becomes viscous 
and dark colored. The optical rotation of the distillate, removed at 
ordinary pressure, was found to be only —5.4° (10 cubic centimeters, 
30°), while that of the steam-distilled product under the same conditions 
is—21°. This lowering of the rotation is due to the heating to which the 
oil is subjected by the former process, it being ascertained that by con- 
tinued heating at the boiling point, the optical activity is entirely 
destroyed. 
A study of the effect of heat upon the viscosity of the oil demonstrated 
that very little if any change occurred when it was kept at 250° for ten 
hours; the specific gravity of the product increased by 0.002, but there 
was no noticeable alteration in the boiling point. 
Non-volatile portion —This consisted of about 27 per cent of the total 
and remained as a residue after. the distillation of the lower boiling 
substances at 40 millimeters was completed ; after this point, even under 
greatly diminished pressure, decomposition began. The residue in part 
consisted of a solid body which separated on the addition of alcohol. It 
was recrystallized from the latter solvent, filtered to as dry a condition 
as possible, and then completely desiccated im vacuo. 
The erystals cling together and are flaky and soft, melting at 63° to 65°. Their 
boiling point is very high, but heating in a test tube over a free flame causes no 
decomposition. The body is unaffected by alcoholic potash and it does not evolve 
hydrogen when treated with melted sodium. 
0.2680 gram substance gave 0.8394 gram CO, and 0.3602 gram H,0. 
0.1494 gram substance gave 0.4658 gram CO, and 0.2010 gram H,0. 
Found 
(1) (2) 
C 85.43 85.02 
H 14.94 14.61 
Total 100.37 99.63 
It is evident from the analyses that the body is a hydrocarbon. In 
chloroform solution it does not add bromine and on warming with dilute 
potassium permanganate the latter is not decolorized. Substances of the 
same type have previously been observed in resinous products and essential 
oils.” 
2 Gildemeister und Hoffmann: Die Aetherischen Oele, 158. 
