Xlviii. ABSTRACT OF PROCEEDINGS. 



be cumin-aldehyde. The aldehyde occurs in greatest amount in 

 the oils obtained from members of the group of Eucalypts known 

 in Australia as the " Boxes." The true boxes, E. hemiphloia, 

 E. albens, and E. Woollsiana, contain it in the largest quantity. 

 The oil was obtained from E. hemiphloia, this tree growing plenti- 

 fully at Belmore, in the neighbourhood of Sydney. 1,000 cc. of 

 the crude oil was distilled, and the constituents distilling below 

 190° C. removed, the remainder of the oil was agitated with acid 

 sodium sulphite with which it readily formed a solid compound, 

 the pure aldehyde was easily obtained from this by the usual 

 methods. The product was steam distilled, 33 cc. of the pure 

 aldehyde was thus obtained from a litre of the crude oil, equal to 

 3*3 per cent. The specific gravity of the aldehyde at 15° C. was 

 •9477. The specific rotation was [a] D - 49*17, this somewhat high 

 laevorotation causes those oils containing it to be laevorotatory, 

 although mostly devoid of phellandrene. It is this aldehyde that 

 causes the oil of E. cnerifolia of South Australia to be laevo- 

 rotatory. The pure aldehyde has an aromatic odour and is slightly 

 yellowish in tint. It was soluble in the usual solvents. The 

 oxime was readily formed, and when purified from alcohol, it 

 melted at 84° C; and by preparing the oxime from the pure 

 aldehyde obtained from the higher fractions of several oils, as 

 E. cnerifolia, E. albens, E. Woollsiana, etc., it was shown that 

 only this aldehyde is present in this class of oils, as this oxime 

 melted at 84° C. also. The hydrazone was also readily obtained, 

 it melted at 105° 0. The aldehyde reduced an alkaline silver 

 solution with the formation of a silver mirror, and also answered 

 to Schiff's reaction. Analysis showed the formula of the aldehyde 

 to be C 10 H 14 O. When the aldehyde was oxidised with potassium 

 bichromate a crystallised acid was obtained, the aldehyde group 

 being oxidised to carboxyl in the usual way. This acid melted 

 sharply at 110° O. It is soluble in boiling water, very soluble in 

 alcohol and in ether. When the aldehyde was oxidised with an 

 alkaline solution of potassium permanganate, energetic action took 

 place, with the formation of eucalyptol or cineol as one of its 

 products. The acid also obtained at the same time melted at 



