244 



for acetic acid is 91-35 per cent., this result shows tliat no other \olatile acid 

 than acetic was present. 



The separated oil containing the alcohols was redistilled, when the greater 

 portion came over between 217° and 229° C. This had the marked rose odour of 

 geraniol, was inactive to light, and had specific gravit\- at 18° C. = o-88i8. These 

 results alone were strong evidence for geraniol, and it was not e\'en necessary to 

 separate the alcohol in a perfectly pure condition by means of its calcium chloride 

 compound. When treated in the cold with the usual potassium bichromate 

 oxidising mixture, the marked odour of citral was obtained. A quantity was 

 then carefully oxidised with the more dilute oxidising mixture, and the citral 

 which formed extracted and purified. The oil which remained on the remo^'al of 

 the ether had the marked odour of citral, and when treated with pyroracemic 

 acid and yS-naphthylamine, as suggested by Doebner, gave citryl — yS-naphtho- 

 cinchoninic acid, which melted at 197-198° C. The principal constituents in the 

 oil of this Callitris are thus shown to be geranyl-acetate and free geraniol. In 

 the oil of no other species of Callitris has such a large amount of geraniol been 

 found. 



No. 2. — This material was collected at Swansea, Tasmania, 3rd June, 1908. 

 The leaves and terminal branchlets alone were used, the fruits ha\'ing been removed 

 before distillation, and these treated separately. 600 lb. of branchlets gave 20 oz. 

 of oil, equal to 0-208 per cent. 



Although the fruits were distilled for six hours, yet not sufficient oil was 

 obtained to separate. The general appearance, too, of the fruits is not at all 

 promising for oil. 



The leaf oil was amber coloured and had an odour strongly indicating that 

 of geranyl-acetate. It was insoluble in ten vohimes of 70 per cent, alcohol, but 

 was soluble in one volume of 80 per cent, alcohol, and in all proportions after. 



The specific gravity of the crude oil at 15° C. = 0-8976 ; rotation a,, = -5-8° ; 

 refractive index at 15° = 1-4739. The saponification number after boiling was 

 179-3, equal to 62-75 per cent, of ester. In the cold, with two hours' contact, the 

 saponification number was 177-7, equal to 62-2 per cent, ester, or 48-g per cent. 

 of alcohol; an identical result was obtained with four hours' contact. This result 

 shows that the whole ester was geranyl-acetate. A portion of the oil was acetylated 

 in the usual way, when it had a rotation au = — 5'4° C. The saponification 

 number after boiling was I95'i, representing 629 per cent, total alcohol in the 

 oil. In the cold, with two hours' contact, it was i92"9, representing 62 per cent, 

 total alcohol, so that practically the whole of the alcohol in tlic oil of tliis species 

 is geraniol, and 14 per cent, of free geraniol was present in this sample. 



The results of these analyses show that ovc-r 70 per cent, of the oil of C. 

 Tasmanica consists of geranyl-acetate and free geraniol. 



