748 Wisconsin Academy of Sciences, Arts, and Letters. 
contained a-pinene; m. p. of nitrasoehloride 104-105° ; m. p. of 
nitrolpiperidine 117°. The small amount of oil distilling between 
160-170° was examined for /Fpinene with negative results, 
Limonene was present, m. p. of tetrabromide 124°, while phel- 
landrene and sylvestrene were absent. 
The oil obtained by saponification of the ester fractions was 
oxidized with a saturated solution of potassium permanganate. 
Steam distillation yielded a small amount of oil having a strong 
odor of camphor. From the oxidation liquors an acid was ob¬ 
tained that sublimed readily and crystallized from water in thin 
needles. By titration of a known weight with standard alkali 
and by determination of its melting point, 183-184°, this acid 
was found to be anisic acid, indicating the presence of methyl- 
chavicol in the oil. A small amount of green oil was present in 
the higher fractions. 
The fact that the oil from the needles of this species consists of 
terpenes while the oil from the wood is mainly n-heptane has a 
particular significance. It proves that in the digger pine at 
least, if not in all conifers, that the phytochemical processes tak¬ 
ing place in the leaves and in the wood are entirely different. 
The composition of the leaf and twig oil is the following: 
n-heptane 3% ; 1-a-pinene 58-59%; 1-limonene 18%; ester as 
bornyl acetate 3.5% ; free alcohol as borneol 6%; methylchav- 
icol (?) ; ‘‘green oil” 2-3%. 
The Leaf and Twig Oil of Lodgepole Pine (Finns contorta 
Loud.) 1 
The sample examined had the following constants: d 15 ° 0.8690 ; 
n Dl5 ° 1.4831 ; a D2 o 0 -17.84 0 ; acid No. 0.90 ; ester No. 6.02 ; ester 
No, after acetylation 32.30 ; yield of oil 0.234%. 
An aqueous extract of the first fraction contained furfural. 
This fraction b. p. 156-160°, d 15 ° 0.8662, aD 25 °-24.85°, consisted 
chiefly of a-pinene; m. p. of nitrosochloride 103.0-103.5°; m. p. 
of nitrolpiperidine 118°. Camphene was shown to be present by 
conversion into isoborneol m. p. 205-207° after one crystalli¬ 
zation. The principal terpene in the oil was /3-pinene, the 
nopinic acid melting at 127°. The fraction b. p. 170-180° con¬ 
sisted largely of 1-phellandrene, the nitrite of which melted at 
102°. Phellandrene is the chief terpene present in the turpen- 
1 Jour. Ind. Eng. Chem. 7 (1915) 24. 
