37 2 



J>) TERPINEOL FROM THE OIL OF E. PHELLANDRA. 



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

 (, ill. ird Gordon, Ltd., at Braidwood, New South Wales, in November, 1919. It 

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

 a o r 5"75°j refractive index at 20 C. = 1-4708; soluble in i| 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 : — 



Below 190 C. 



Above iyo° C 



Specific gravity at 15 C. 

 Rotation a D 



Refractive index at 20° 

 Solubility in 70 per cent, alcohol 

 Cineol by resorcinol 



,, by phosphoric acid 

 Saponification number, hot 

 cold 



0-8973 

 - i6-o° 

 1-4670 

 10 volumes 

 62 per cent. 

 33 per cent. 



39-3 



iS-4 



0-935-2 

 - 6-o° 

 1-4836 

 I volume. 



105-7 

 45-9 



By repeated fractionation of the portion boiling above 190 at 10 

 millimetres, 67 c.c. were obtained boiling at 100-101 C. (uncorr.). This had 

 the following characters :— 



Specific gravity at 15 C. ... ... ... ... ... = 0-9382. 



Rotation a D ... ... ... ... ... ... - 14-25° 



Refractive index at 20° C. = 1-4817. 



Phenylurethane melted at ... ... ... ... 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. phcllandra is thus shown to have a higher 

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



(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. ... 



+ 



Rotation a_ 



Refractive index at 20 



Phenylurethane melted at 

 When repeatedly shaken with 5 per 

 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. 



0-930. 

 6o-i° 

 1-4840. 

 no C. 

 cent, sulphuric acid, terpin hydrate was 



