— 122 — 



formed until it has been found possible to prepare derivatives from it. 

 Its high specific gravity probably precludes the possibility of the body 

 belonging to the terpene series proper. 



The hydrocarbon is completely saturated and at ordinary temperature 

 remains unaffected by permanganate. Unsuccessful attempts were made 

 to hydrate it, nor was any result obtained by acting with hydrochloric 

 acid upon the alcoholic solution. The quantity of solid chloride obtained 

 was insufficient for identification. As soon as fresh material is available, 

 we will examine the body further. 



Semmler 1 ), in the course of his researches into the constitution of the 

 santalols, and respectively of the eksantal series, had obtained from tri- 

 q/doeksantalic acid, by splitting off carbon dioxide gas, a hydrocarbon 

 designated as nor-triq/c/oeksantalane. Because of its origin he assigns to 

 this body the formula Ci Hi 6 and he regards it as the parent substance of 

 all santalol derivatives which have so far been described. But the more 

 recent investigations of Semmler-) have shown that triq/doeksantalic acid 

 possesses twelve carbon atoms, from which it would seem that the correct 

 formula of nor-tric^doeksantalane is CnHi 8 , and Semmler's analyses agree 

 with this view. 



irbon from sandalwood oil 



Nor 



-trici/doeksantalane 





(according to Semmler) 



B. p. 183° 





183,5° 



d 20 o 0,9092 





0,885 



a D — 23°55 f 





— 11° 



n D 2oo 1,47860 





1,46856 



Mol. refr. 46,74 





47,15. 



The remarkable fact that the separate constituents of sandalwood oil, 

 such as santalol, santalene, teresantalic acid, santene, santenone, santenol, 

 nor-triq/c/oeksantalal, and teresantalol, which are described in detail 

 below, exhibit mutual generic relationships makes it very probable that 

 the tricyclical hydrocarbon from sandalwood oil is identical with, or at 

 least closely allied to, Semmler's nor-triq/cZoeksantalane. 



Nor-triq/cfoeksantalal. The fractions with a boiling point exceeding 

 that of santenone (b. p. 80 to 100° at 7 mm.; di 5 o 0,987 to 0,996; « D — 23°9'), 

 consisted of a mixture of several compounds in which, besides unknown 

 constituents, we were able to detect the presence of two ketones, one 

 aldehyde and one alcohol. It was evident that santalone, the ketone 

 CnHieO which had already been isolated by F. Muller, must also be included 

 in these fractions. We tried to separate it with semicarbazide, but the 

 yield of semicarbazone from all fractions was exceedingly small and the 

 product obtained formed a mixture which was difficult to separate. 



*) Berl. Berichte 40 (1907), 1124; Report October 1907, 85. 



-) Berl. Berichte 43 (1910), 1722; also see the present Report, p. 129. 



