64 



had ratlin a pleasant odour, somewhal aromatic. Pinene was the principal 

 low-boiling terpene, and phellandrene was absent. Cineol was present in fair 

 amount at time of distillation. The sesquiterpene was a pronounced constituent. 

 The crude oil had specific gravity at 15 = 0-9132; rotation a B + 3-41°, 

 refractive index at 20 = 1-4694, and was soluble in 6 volumes 70 per cent. 

 alcohol. The saponification number for the esters and free acid was 6-9. 



On rectification, _> per cent, distilled below 172 C. (corr.). Between 

 172 174 , 21 per cent, distilled; and between 174-193, 59 per cent, distilled; 

 the remainder consisted largely of the sesquiterpene. The fractions gave the 

 following results : — 



First fraction, sp. gr. at 15 C. = 0-9042; rotation a D + 4-16°. 

 Second ,, ,, „ = 0-9092; ,, + 2-63°. 



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

 was 31 per cent. (O.M.).* 



Material of this species was also obtained at Canterbury, N.S.W., in Julv, 

 1897. The colour, odour, constituents, and physical properties of the crude oil 

 were practically identical with those of the previous sample. The yield of oil 

 was o-8 per cent. The crude oil had specific gravity at 15° C. = 0-9122; rotation 

 "d-+ 4"8°. and was soluble in 7 volumes 70 per cent, alcohol. 



The cineol, determined by the phosphoric acid method, was 28 per cent. 

 (O.M. . The solubility in alcohol of the crude oil of this species increased as 

 it became richer in cineol, and" at the end of three and a half vears it was soluble 

 in 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. The increase in cineol was quite 

 pronounced. This was noticed before the first edition of this work was published, 

 and a note was added at the time recording this peculiarity. 



The crude oil and the rectified portion gave the following results. 86 per 

 cent, distilled below 190 C. : — 



Crude oil, sp. gr. at 15 C. = 0-9393 ; rotation a a + 3-8° ; refractive index at 



20° = 1-4707. 

 Fraction, ,, „ = 0-9158 ; rotation a D + 2-5° ; refractive index at 



20 = 1-4636. 

 The cineol was determined by the resorcinol method in the fractionated 

 oil, and calculated for the crude oil; the result was 72 per cent. By the rapid 

 phosphoric acid method it was 58 per cent., when calculated for the crude oil. 

 The saponification number for the esters in the rectified portion was 11-7, and 

 after acetylation 24-7. It is thus evident that bodies other than cineol, 

 alcohols and esters, were absorbed bv resorcinol. 



* (O.M.) denotes original determination by phosphoric acid for the him edition of this work. Sec also the 

 article on cineol (or eucalyptol), 



