﻿36 CLOVER. 



IV,C, purified, gave the following numbers : 



(1) 0.1504 gram substance gave 0.3917 gram CO, and 0.1163 gram H 2 0. 



(2) 0.18S7 gram substance gave 0.4917 gram CO. and 0.1420 gram ELO. 



(3) 0.2388 gram substance gave 0.6245 gram CO, and 0.1850 gram H.O. 



Found 



(1) (2) (3) 



Per cent. Per cent. Per cent. 



C=71.03 71.07 71.32 



H= 8.59 8.36 8.79 



Analysis (3) was made of a middle fraction of the substance, redistilled in 

 a vacuum. 



If we consider that these oils belong either to the terpene or sesqui- 

 terpene class, and are composed of the substances having the formula 

 C 10 H 16 , C 15 H 24 or their oxygen derivatives, then taking the boiling point 

 into consideration we have in general three posibilities, namely, (1) a 

 sesquiterpene or (2) a dioxygen derivative of a terpene or (3) a mono- 

 oxygen derivatives of a sesquiterpene may be present. The sesquiter- 

 penes are almost insoluble in dilute alcohol; the solubilities in 55 per cent 

 alcohol (by volume) respectively of pure caclinene prepared from the 

 hydrochloride and pure cedrene, distilled from oil of cedar, were deter- 

 mined and found to be practically nil. The different, high-boiling oils 

 from elemi were then tested with the result that they showed a consider- 

 able solubility in 55 per cent alcohol; this solubility which in several 

 instances is given in the table, varied just as do their other properties. 

 In a few instances. there was evidence of a trace of sesquiterpene, but 

 the amount was inconsiderable. That the soluble constituents of the oil 

 would have no great effect upon the solubility of a sesquiterpene, if such 

 a substance were present, was shown by adding a small amount of the 

 latter to several of the clear solutions. 



The solubility of oil XVI,B, purified, the last one of the series, is very 

 close to that of the pure sesquiterpene alcohol XII,B, purified (see 

 p. 34), so that the assumption that we have here a substance similar 

 to the latter seems to be verified. Moreover, the analysis of XVI,B, 

 purified, shows that its composition is close to that of a sesquiterpene 

 alcohol. On the other hand, the member at the other extreme of the series 

 IV,C, purified, has a much greater solubility in 55 per cent alcohol, this 

 property being remarkable. Considering the analysis and the boiling 

 point, the latter substance is a dioxygen derivative of a terpene and is 

 nearly pure ; all of its properties are in accord with this assumption. The 

 numbers obtained on analysis show too great a difference from any formula 

 which can be calculated for the oil for it to be considered as being pure. 

 C 10 H 14 2 requires 72.28 per cent for carbon and 8.44 per cent for hy- 

 drogen. This oil is slightly yellow in color, of a very mild, pleasant 



