CRYSTALLINE CAMPHOR OF EUCALYPTUS OIL. 89 



In the spring time phellandrene appears in greatest amount in the 

 oil of this species, while in the autumn it is almost or quite absent. 

 As the phellandrene diminishes in this oil, the eucalyptol increases 

 in quantity, other alterations also taking place. In a paper 1 by 

 Mr. Baker and myself, published July 1898, analyses are given of 

 the oil of this species, in which a good quantity of eudesmol had 

 been found. A reference to that paper will shew that only about 

 48 per cent, distilled below 183° C, and that the oils contained a 

 fairly large fraction boiling above 268° C. consisting largely of 

 eudesmol. It was from the high boiling constituents of this oil 

 that the eudesmol was obtained for the purpose of this research. 

 On opening some months afterwards, the glass stoppered bottle in 

 which the crude oil had been stored, it was found that there had 

 been absorption of the oxygen from the air filling the vacant space 

 above the oil, there being apparent suction on the stopper of the 

 bottle ; little notice was taken of this at the time, but the same 

 thing having occurred again investigation of the contents was 

 made to determine if possible the result of the alteration. It 

 was then found that the greater portion of the high boiling fraction 

 containing the eudesmol had disappeared, and that the oil had 

 become much richer in eucalyptol. The following is the analysis 

 of this oil after having been kept in the crude condition for nine 

 months. No pinenes were found, nor could phellandrene be 

 detected. On redistillation only a few drops came over below 

 170° C, but between that temperature and 1755° C. 27 per cent, 

 had distilled, and by 182*8° C. 74 per cent, had been obtained 

 against 48 per cent, distilling below 182*8° 0. when originally 

 investigated. The fractions were divided as follows: — 

 Below 175*5° C. = 27 per cent. = First fraction 

 Then to 182*8° 0. = 47 „ = Second „ 

 268-6° C. = 10 „ = Third 

 276-8° C. = 11 „ ... Fourth „ 

 The fourth fraction only contained eudesmol in very small quantity 

 at this second distillation, and only crystallised on long standing. 



1 On the Stringybark Trees of N.S. Wales— Proc. Eoy. Soc. N.S. Wales, 

 July 6, 1898. 



