37 2 



(ft) TERPINEOL FROM THE OIL OF E. PHELLANDRA. 



The " second hour " oil of this species was distilled for us by Messrs. 

 Gillard Gordon, Ltd., at Braidwood, New South Wales, in November, igig. It 

 had the following characters: Specific gravity at 15 C. = 0-9035; rotation 

 a D - - 15-75; refractive index at 20 C. : : 1-4708; soluble in ij volumes 70 per 

 cent, alcohol, and contained a considerable amount of phellandrene. The cineol, 

 determined by the resorcinol method in the portion distilling below 190 C. was 

 52 per cent, when calculated for the crude oil. By the phosphoric acid method the 

 result was 30 per cent. The saponification number for the esters was 10-3 ; after 

 acetylation it was 57 by heating and 25-3 in the cold with two hours' contact. 



4,000 c.c. were distilled, when 80 per cent, came over below 190 C. This 

 fraction, and the portion boiling above that temperature, gave the following 

 results : 



By repeated fractionation 

 millimetres, 67 c.c. were obtained 

 the following characters : 



Specific gravity at 15 C. . 



Rotation D 



Refractive index at 20 C. 



Phenylurethane melted at 



of the portion boiling above 190 at 10 

 boiling at 100-101 C. (uncorr.). This had 



= 0-9382. 



- - 14-25 



= 1-4817- 



112 C. 



When shaken with 5 per cent, sulphuric acid a good yield of terpin hydrate 

 .was eventually obtained. 



The terpineol in the oil of E. phellandra is thus shown to have a higher 

 laevo-rotation than has that in the oil of E. Australiana. 



(c) TERPINEOL FROM THE OIL OF E. CARNEA. 



The oil of E. carnea had a high saponification number, and an attempt 

 was made to determine the alcohol of the ester. The oil was saponified in the 

 ordinary way, afterwards rectified, and the fraction boiling below 190 C. removed. 

 The higher boiling portion was repeatedly rectified under reduced pressure, when 

 a fraction distilling at 100-103 C. at 10 millimetres was eventually obtained. 

 This had the following characters : 



Specific gravity at 15 C. ... ... ... ... ... = 0-930. 



Rotation a D ... ... ... ... ... ... + 60-1 



Refractive index at 20 ... ... ... ... ... = 1-4840. 



Phenylurethane melted at ... ... ... ... 110 C. 



When repeatedly shaken with 5 per cent, sulphuric acid, terpin hydrate was 

 formed in some quantity. The terpineol in the oil of this species was thus shown 

 to have a considerable dextro-rotation. The ester was chiefly terpinyl-acetate. 



