L-PHELLANDRENK IN THE OIL OF MELALEUCA ACUMINATA. 16] 
On rectifying the terpenes as thus prepared practically 
nothing distilled below 166° (uncor.). Between 166— 168° 
39 per cent. distilled; between 168 —172° 39 per cent, came 
over, leaving 22 per cent. boiling above 172°. The two 
fractions gave the following results :— 
Sp, gr. at 15° Rot. ap Ref. ind. at 20° 
First fraction 0°8568 — 20°8° 1°4735 
Second ,, 0°8542 — 21°2° 1°4794 
Apparently a very small quantity of pinene was present 
in the first fraction, judging from the boiling point and 
physical constants; but the reaction for phellandrene was 
most distinctive. Thenitrosite was prepared using sodium 
nitrite and acetic acid in the usual way, and when purified 
by dissolving in chloroform and precipitating with methyl 
alcohol, melted at 105-6". It was dextrorotatory and 0°1552 
gram. in 10 c.c. chloroform rotated the ray 1°0° to the left 
in a decimetre tube; the specific rotation was thus [a]p 
+64°4°. 
It is thus evident that the principal terpene in the oil of 
Melaleuca acuminata is levo-phellandrene, and judging 
from some of its reactions it is probable that when com- 
pletely investigated this phellandrene will be found not to 
be identical in constitution with the t-phellandrene occur- 
ing in the oils of species belonging to the °‘ Peppermint 
group”’ of Eucalypts. This matter is to receive further 
investigation. 
The ester and free alcohol in the oil of this Melaleuca 
were but small in amount, as was also the sesquiterpene. 
The alcohol was high boiling and probably terpineol. 
K—October 4, 1922. 
