ZOI 



On rectification i per cent, distilled below 173 C. (corr.). The odour of 

 valeraldehyde was pronounced in this portion. Between 173-194, 67 per cent, 

 distilled; between 194-245, 8 per cent, came over, and between 245-278, 19 

 per cent, distilled. These fractions gave the following results : 



First fraction, sp. gr. at 15 (". :: 0-9078; rotation </ - 0-3; refractive 



index at 20 i -4636. 

 Second ,, ,, 0-9154; rotation a a + 0-3; refractive 



index at 20 = 1-4707. 

 Third ,, : 0-9396; rotation a D + 12-4; refractive 



index at 20 = 1-5000. 



The cineol was determined by the resorcinol method in the first fraction ; 

 when calculated for the crude oil the result was 51 per cent. By the phosphoric 

 acid method it was 40 per cent, when calculated for the crude oil. 



The first fraction had a yellowish tint, due to the influence of the phenols, 

 and was rich in cineol. The saponification number was only 2-3, so that low- 

 boiling esters were practically absent. 



A portion of the oil boiling above 190 was acetylated, the saponification 

 number for this was 74-6. This high number was due to the eudesmol, which 

 was present in the liquid form. 



Determination of the higher boiling portion. 100 cc. of the oil boiling above 

 190 C. were again distilled. 3 per cent, came over below 183 C. Between 

 183-208, 19 per cent, distilled ; between 220-265, 19 per cent, came over, and 

 between 265-290, 50 per cent, distilled. These fractions gave the following 

 results : 



First fraction, sp. gr. at 15 C. = 0-9179; rotation a D + 1-4; refractive 



index at 20 = 1-4684. 

 Second ,, ,, = 0-9337; rotation <I D + 3-6; refractive 



index at 20 = 1-4874. 

 Third ,, ,, ,, = 0-9523; rotation a D + 18 ; refractive 



index at 20 = 1-4983. 



The first fraction contained a good quantity of cineol. It is possible that 

 terpineol was present in the second fraction, as the indications were for that 

 alcohol. The third fraction consisted largely of the liquid form of eudesmol and 

 the sesquiterpene. 



Both the second and third fractions were acetylated with the following 

 results : - 



Second fraction, saponification number before = 4-8 ; after = 96-8. 

 Third ,, ,, ,, = 2-8; after = 91-8. 



This result indicates that about 35 per cent, of eudesmol was present in 

 the third fraction. 



One hundred cubic centimetres of the crude oil were distilled under reduced 

 pressure, and the lower boiling portion removed. The oil distilling between 

 138-148 C. under 7 millimetres pressure was again distilled and separated into 

 two fractions; one distilling between 130-134 C., under 7 millimetres, the. other 

 between 140-146 C. under 5 millimetres pressure. The two fractions gave the 

 following results : 



First fraction, sp. gr. at 15 C. = 0-9640: rotation a n + 8-6; refractive 



index at 20 = 1-5023. 

 Second ,, ,. = 0-9697; rotation a n + 15-4; refractive 



index at 20 = 1-5058. 



A portion of the second fraction was boiled with water under a reflex for 

 four days, but the crystalline form of eudesmol was not obtained. A portion 

 seeded with eudesmol had not crystallised after fourteen days, although the 



500680 



