Schoryer—-Chemistry of American Conifers. 735 
galactans were characteristic of the conifers as they were de¬ 
tected in five additional species. The significance, if any, of 
their occurrence remains to be determined. 
Examination of Oils and Oleoresins 
Oil of Port Orford Cedar [Chamaecypans lawsoniana (Murr.) 
Parlatore]. 1 
This species is limited in its distribution to southwestern Ore¬ 
gon and northern California. Selected pieces of resinous wood 
when distilled with steam gave 10 per cent of oil having the 
constants: d 15 ° 891; n Dl5 ° 1.477. After standing in a tightly 
stoppered amber-colored bottle for four years, the oil had the 
constants: d 15 ° 0.9061; n Dl5 ° 1.4806. On rectification by shak¬ 
ing with sodium carbonate solution and distillation with steam 
the, oil lost 16.4 per cent by volume. The rectified oil had nearly 
the same properties as the original oil as shown by the following; 
d 16 ° 0.8905; n D i 5 ° 1.4758; a D2 5 ° +39.60; acid No. 0.30; ester 
No. 32.8; ester No. after acetylation 71.57. 
A very pure d-a-pinene was obtained by repeated fractiona¬ 
tion, the constants of which were as follows: b. p. 156.0 - 156.1° 
(760 mm.) ; d 15 ° 0.8631; n Dl5 ° 1.4684; specific rotation [a] D + 
51.52° ; molecular refraction, M — 43.88; calculated for C 10 H 16 
f, 43.54. This is the highest previously recorded rotation for 
a-pinene. Vezes 2 had found for d-a-pinene from Grecian tur¬ 
pentine oil the rotation [a] D +48.4°, and for 1-a-pinene from 
eucalyptus oil (E. laevopinea) Smith 3 had found [a] D i 9 0 -48.63 0 . 
In conformity with its high rotation it was found impossible to 
obtain a nitrosochloride from the purified pinene; oxidation with 
alkaline K 2 Mn 2 0 8 gave d-pinonic acid ( [a]D+92.69°) m. p. 
68-69°, the semicarbazone of which melted at 203-205°. 
Dipentene was detected by means of the tetrabromide m. p. 
124°. Saponification of the ester fractions gave an oil containing 
d-borneol as shown by formation of d-camphor on oxidation; 
the semicarbazone melted at 236-237°. Cadinene, m. p. of dihy¬ 
drochloride 117-8°, occurred in the high boiling fractions. 
Analysis of the silver salts of the combined acids showed them 
to consist of silver acetate and silver caprinate: Ag in silver 
1 Jour. Ind. Eng. Chem.,- 6, 631 (1914). 
2 Bull. Soc. Chim. (4) 5, 932 (1909). 
3 Jour, and Froc. Roy. Soc. N. S. W. 32, 195 (1898). 
