Schorger—Chemistry of American Conifers. 739 
The Oleoresin of Jeffrey Pine (Pinus Jeffreyi.) 1 
Five samples of oleoresin were examined in all. The yield of 
oil varied from 8.81-11.25%, the average being 9.96%. The oils 
had the following properties: d 15 ° 0.6951-0.7110; n Dl5 ° 1.3927- 
1.4060. On fractionation 92.45% of this oil distilled between 
98.2-113.0° principally between 99 and 102°. Redistillation 
using a Hempel column gave an oil whose properties (b. p. 98.4° 
and d 15 ° 0.6881) showed it to consist of n-heptane. 
The residue left above the temperature 113° distilled prin¬ 
cipally between 200-215°. A portion of the oil formed a floc- 
culent precipitate with sodium bisulphite and showed other prop¬ 
erties characteristic of an aldehyde. A semicarbazone melting 
at 91-92° was prepared. Owing to lack of material no further 
derivatives could be prepared. Judging from the lemon-like 
odor and the m. p. of the semi-carbazone it was thought that 
citronellal 2 was probably present, the racemic form of citron- 
allal semicarbazone melting at 96°. 
The colophony had an acid No. of 147.6, a saponification No. 
178.1, and contained 12.5 per cent of resene. Using acetone 
as the solvent, resin acid crystals melting at 137-8° were ob¬ 
tained, while when crystallized from acetone containing hydro¬ 
chloric acid they melted at 145-6°. The colophony of this spe¬ 
cies crystallizes readily differing in this respect from the colo¬ 
phony of P. sabiniana which also yields heptane. 
The resin crystals obtained from the crude oleoresin melted at 
170-171°. The silver salt was analyzed as follows: 0.3926 g. of 
silver salt gave 0.1027 g. Ag — 26.16% Ag. Silver abietate, 
Ag (C 20 H 29 O 2 ), requires 26.37% Ag. 
Leuchtenberger 3 extracted the colophony of Jeffery pine with 
ammonium carbonate and sodium carbonate solutions obtaining 
the following acids: a-jeffropinic acid C 10 H 14 0 2 , m. p. 160-161° ; 
/bjeffropinic acid, C 12 H 18 0 2 , m. p. 81-82°; a-jeffropinolic acid, 
C 14 H 20 0 2 or C 14 H 22 0 2 , m. p. 117-118° and /3-jeffropinolic acid 
having the latter formula, m. p. 77-78°. None of these acids 
agree in melting point with those obtained by the author. The 
1 Jour. Ind. Eng. Chem. 5 (1913) 971. 
2 Schimmel & Co. (Report, Oct. 1914-April 1915, p. 45) working with a 
considerable quantity of material showed that the non-heptane constituents 
consisted of n-decylic aldehyde, linalool, and methylchavicol. 
3 Arch. d. Pharm. 245 (1907) 701. 
