164 



The crude oil had specific gravity at 15 C. ;= 0-9125; rotation a D + 7-2; 

 refractive index at 20 = 1-4689, and was soluble in i volumes 70 per cent. 

 alcohol. The saponification number for the esters and free acid was 13-3. 



On rectification 2 per cent, distilled below 169 C. (corr.). Between 

 169-171, 25 per cent, distilled ; between 171-183 , 60 per cent, distilled ; between 

 183-260, 5 per cent, came over, and between 260-275, 4 per cent, distilled. 

 These fractions gave the following results : 



First fraction, sp. gr. at 15 C. = 0-9045; rotation a D + 9-58. 

 Second ,, ,, ,, = 0-9110; ,, + 5-6 . 



Third ,, ,, ., = 0-92.20; ,, not taken. 



Fourth ,.. ,, ,, = 0-9459; 



The cineol, determined by the phosphoric acid method in the crude oil, 

 was 56 per cent. (O.M.). The pinene, when separated, readily formed the 

 nitrosochloride, which melted at the correct temperature. 



Material of this species was also obtained from Katoomba, N.S.W., in May, 

 1900. The oil was practically identical with the above. The yield of oil was 

 I per cent. The specific gravity of the crude oil = 0.9117; optical rotation 

 D + 4-35. The cineol, determined by the phosphoric acid method in the crude 

 oil, was 55 per cent. (O.M.). Crystallised eudesmol was present, also pinene, 

 but not phellandrene. The esters were valeric acid ester and an acetic acid 

 ester, as the presence of both these acids was chemically determined. The crude 

 oil formed a clear solution with i^ volumes 70 per cent, alcohol. 



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

 August, 1919, the oil was again analysed. Not much alteration had taken place 

 during the twenty-one years the oil had been kept ; and no increase in cineol 

 was observed. 90 per cent, distilled below 190 C. The crude oil and the 

 fraction gave the following results : 



Crude oil, sp. gr. at 15 C. = 0-9127 > rotation D + 4-3; refractive index 



at 20 = 1-4694. 

 Fraction ,, ,, = 0-9078; rotation a D + 4-0; refractive index 



at 20 1-4663. 



The cineol was determined by the resorcinol method in the fractionated 

 portion and calculated for the crude oil ; the result was 65 per cent. By the 

 phosphoric acid method it was 56 per cent, when calculated for the crude oil. 



In Wittstein's work (trans. F.v.M.), page 148, the oil of E. goniocalyx is 

 stated to be pale yellow, of pungent, penetrating, rather disagreeable odour; 

 taste, exceedingly unpleasant; specific gravity, 0-918; boils at 152-175. These 

 results agree closely with our own, thus indicating that the material had been 

 distilled from the species stated. The presence of a fair amount of dextro-rotatory 

 pinene is also indicated by Wittstein's figures of boiling-point, whilst the unpleasant 

 odour mentioned is due to the predominance of the volatile aldehydes, and also 

 perhaps to the esters. The yield of oil from this species, prepared for the 

 Exhibition of 1862, was i per cent., which also agrees with our results. The 

 relative constancy of constituents in the oil of the same species of Eucalyptus 

 is thus again illustrated. 



