328 



were present; the saponification number of the acetylated oil was 39-74, whilst 

 that for the original oil was 10-05; the increase was thus 29-69, due to the free 

 al( ohols present. This result represents about 5 per cent, of free alcohol, considered 



• 1- C, M . 1 » 



The above samples were mixed together, stored in the dark, and in December, 

 1919, the oil was again analysed. It had specific gravity at 15 C. = 0-9138; 

 rotation a B ro-8°; refractive index at 20 = 1-4864; ketone estimation 38 per 



cent. 



On rectification, under reduced pressure, the following results were 

 obtained : 



Below ioo° C. at 10 millimetres pressure = 60 per cent. 

 Between 100-108 ,, ,, =23 



Between 108-128 ,, ,, =5 



Between 128-152 ,, ,, = 11 



The first fraction had specific gravity at 15 C.=o-88i8; rotation a D — i-8°; 

 refractive index at 20 = 1-4818 ; it contained both cineol and piperitone. 



On repeated fractionation, a substance was obtained having specific 'gravity 

 at 15 C. = 0-864; rotation a D + n-6°; refractive index at 20 = 1-4752 ; it was 

 mostly pinene and gave a nitrosochloride, melting at 104 . 



The second fraction (100-108 ) had specific gravity at 15 C. = 0-940; 

 rotation <?„ -- 31-4°; refractive index at 20 = 1-4854; ketone absorption 91 per 

 cent. On reduction with sodium-amalgam it gave the crystalline body melting at 

 142 . This fraction thus consisted almost entirely of piperitone. The third fraction 

 ( 1 08-1 28 °) differed but slightly from the second fraction, and contained 90 per 

 cent, piperitone. 



The fourth fraction consisted of piperitone, the sesquiterpene, and some 

 alcoholic bodies. 



To determine the approximate amount of the alcohols, the piperitone was 

 removed by treatment with a neutral sodium sulphite solution ; the remainder had 

 specific gravity at 15 = 0-8971 ; rotation a B 4- i-6°; refractive index at 20 = 

 1-4876 ; saponification number 12-4 ; after acetylation it was 36-7, equal to 10 per 

 cent, of a C I5 H, 5 OH alcohol. This sesquiterpene alcohol was probably the liquid 

 form of eudesmol. 



A portion of the original oil was rectified under atmospheric pressure, when 

 42 per cent, distilled below 190 C. This portion had specific gravity at 15 C. = 

 o-88oo ; rotation a B + i-o°; and refractive index at 20 = 1-4811. 



The cineol was determined in this fraction by the resorcinol method ; when 

 calculated for the crude oil, the result was 8 per cent. 



