246 



On rectification, a little acid water and rather a larger amount of 

 objectionable smelling volatile aldehydes came over below 175 C. (corr.). Between 

 175-200, 42 per cent, distilled ; between 200-228, 8 per cent, came over ; 

 the thermometer then quickly rose to 255, and between that temperature and 

 285, 36 per cent, distilled. These fractions gave the following results : 



First fraction, sp. gr. at 15 C. = 0-8796; rotation a D - 2-6 ; refractive 



index at 20 = 1-4650. 

 Second ,, ,, ,, = 0-8913; rotation D - 1-2; refractive 



index at 20 = 1-4679. 

 Third ,, ,, ,, = 0-9007; rotation a D + 4-8 ; refractive 



index at 20 = 1-4875. 



The residue, when poured from the still, became solid when cold ; it 

 was boiled in alcohol and the alcohol separated while hot ; on cooling, a crystal- 

 line paraffin-like substance separated. 



To prove the presence of pinene, another 100 c.c. of the oil were distilled, 

 the added two fractions gave 32 c.c. distilling below 170 C. (corr.) ; it was 

 again distilled, when 15 c.c. was obtained below 162. This contained some 

 cineol, which was removed by shaking with 50 per cent, resorcinol. The remain- 

 ing 9 c.c. of oil had a pinene odour ; specific gravity at 15 C. = 0-8594 ; rotation 

 D + 10; and refractive index at 20 = 1-4690. A small quantity of phel- 

 landrene was still present, but this did not interfere with the formation of the 

 nitrosochloride ; which when purified, melted at the correct temperature for the 

 pinene compound. 



The cineol was determined by the resorcinol method in the portion of oil 

 distilling below 195 C. ; the result indicated that 21 per cent, was present in 

 the crude oil. The high-boiling constituent was most probably the sesquiterpene. 



Material of this species was also obtained at Little Swanport, Tasmania, 

 in June, 1908. The oil was practically identical with that of the above sample, 

 with the exception that a little more pinene was present at this time of the year. 

 The specific gravity at 15 C. = 0-898, and the refractive index at 20 = 1-4724. 

 The saponification number for ester and free acid was 34-3, and the ester consisted 

 mostly of geranyl-acetate. The oil contained the paraffin-like substance in 

 slightly larger amount than did the Hobart sample. 



The investigation of the oil of this species was published by us in the 

 Proceedings of the Royal Society of Tasmania, in October, 1912. 



In September, 1916, we received material of this species for distillation 

 from South Australia, through the kindness of Mr. Walter Gill, the Conservator 

 of Forests of that State. 



The oil was practically identical with that previously distilled from this 

 species growing in Tasmania. This was particularly noticeable through the 

 esters and the solid paraffin, although it contained more of the sesquiterpene. 



The crude oil had specific gravity at 15 C. -- 0-930; rotation a D -- 1-4; 

 refractive index at 20 = 1-4870, and was soluble in i volume 80 per cent, alcohol, 

 but with excess precipitated the paraffin. 



Geranyl-acetate was present to the extent of 14 per cent., as the saponifica- 

 tion number, in the cold with two hours' contact, was 40-7. 



