AUSTRALIAN MELALEUCAS AND THEIR ESSENTIAL OILS. 119 
The cineol was less than 10 per cent., and the oil was 
insoluble in 10 volumes 70 per cent. alcohol, but soluble in 
1 volume 80 per cent. alcohol. The saponification number 
was 6°96 indicating 2°4 per cent. of terpinyl-acetate. The 
free alcohol was determined by boiling the oil for 14 hours 
with acetic anhydride and anhydrous sodium acetate in the 
usual manner; the saponification number had then increased 
to 100°4. Itis recognised, however, that acetic anhydride 
acts upon terpineol as a dehydrating agent, with the form- 
ation of dipentene and other bodies, and according to Heusler 
(the Terpenes, p. 259), the amount of. terpinyl-acetate 
formed by the usual method of acetylating is about 84 per 
cent. of theory; if this statement is accepted as correct 
for the oil of this Melaleuca, then nearly 30 per cent. of 
free terpineol was present, assuming the whole alcohol to 
be that substance. 
The slight colour of the crude oil was due to the phenol 
acting upon the iron of the digester during the process of 
distillation, and, in order to identify this substance, 178 
grams of oil were agitated with dilute alkali in the usual 
manner; the phenol weighed 0°49 gram, equal to 0°27 per 
cent. The product was liquid and had an odour, and gave 
colour reactions with ferric chloride, somewhat closely 
resembling those given by tasmanol—the liquid phenol of 
HKucalyptus oils. 
The test for aromatic aldehydes gave a negative result,. 
the oil being agitated with a 30 per cent. solution of sodium 
bisulphite for several hours. 
On rectification under atmospheric pressure 2 per cent. 
distilled below 168° (uncor.), consisting principally of water 
and volatile aldehydes. Between 168—190° 52 per cent. 
distilled; this fraction was colourless and consisted princi- 
pally of dextrorotatory pinene (nitrosochloride melting at 
103°); dextrorotatory limonene and dipentene (tetrabromide 
