33o 



We were the more anxious to obtain the oil of this species in order to deter- 

 mine its constituents, because those previously stated to occur appeared contrary 

 to what might be expected from a species belonging to the group in which 

 E. Bailey ana is placed botanically. We failed to find either citral or 

 phellandrene, so that evidently the previous statements refer to the oil of a 

 species other than this. 



The crude oil had specific gravity at 15 C. = 0-8928; optical rotation 

 a D + 14; refractive index at 20 1-4767, and was only just soluble in 10 

 volumes 80 per cent, alcohol. The saponification number for the esters and free 

 acid was 2-5 both by the hot and cold method. After acetylation it was 31-7 

 by boiling, and 11-2 in the cold with two hours' contact. 



On rectification less than i per cent, distilled below 157 

 157-161, 5 per cent, distilled ; between 161-166, 30 

 16 per cent.; 174-193, 16 per cent.; 193-254, 5 per 

 26 per cent. These fractions gave the following results : 



Between 

 166-174 

 254-268 

 First 



C. (corr.). 

 per cent. ; 

 cent., and 



fraction, sp. gr. at 15 C. = 



Second 



Third 



Fourth 



0-8631; rotation a D + 27-1" 

 index at 20 = 1-4651. 



0-8682 ; rotation a a + 25-3 ; 

 index at 20 = 1-4660. 



0-8719; rotation a D + 21-6: 

 index at 20 = 1-4672. 



refractive 

 refractive 



refractive 



refractive 

 refractive 



Fourth ,, ,, = 0-8780; rotation a n + 16-3; refractive 



index at 20 = 1-4686. 

 Fifth ,, = 0-8855; rotation a n + 3-5; refractive 



index at 20 = 1-4715. 

 Sixth ,, ,, : 0-9316; rotation D - - i-2 c 



index at 20 = 1-4988. 



The sixth fraction contained a small quantity of a sesquiterpene alcohol, 

 as the saponification number after acetylation was 45. 



The cineol was determined by the resorcinol method in the portion distilling 

 below 190 C. ; when calculated for the crude oil the result was 7 per cent. 



The pinene was prepared in a pure condition, the cineol being first removed 

 by agitating with 50 per cent, resorcinol. The terpene boiled at 155-156 C. ; had 

 optical rotation a D + 30-1; specific gravity at 15 : 0-8633, an d refractive 

 index at 20 = 1-4661. The nitrosochloride was prepared, and this melted at 

 104 C. 



The sesquiterpene was also prepared as pure as possible by refractionation 

 under reduced pressure over sodium. This boiled at 123-125 at 10 

 millimetres pressure; had specific gravity at 15 = 0-924; optical rotation 

 a r> - 3'7; refractive index at 20 1-4964, and gave the colour reactions 

 characteristic for this sesquiterpene. This species falls in our Group I. 



