Origin. The turpentine of the Digger pine or nut pine, Pinus Sabiniana, Douglas3), which is indigenous to the western slopes of the Sierra Nevada in California, yields upon distillation an oil that is totally different in its composition and properties from the other turpentine oils.
1) Journ. Americ. chem. Soc. 23 (1901), 162; Pharm. Review 25 (1907), 363.
2) journ. Americ. chem. Soc. 30 (1908), 872.
3) Synonyms and other botanical information are given by E. Kremers, Pharm. Review 18 (1900), 165.
The oleoresin consists of a tough, but slightly flowing, brownish-yellow mass with a greenish fluorescence and possesses a not unpleasant odor reminding of orange. It is soluble in alcohol, ether, benzene and partly soluble in petroleum ether. A. V. cold 156; S. V. hot 179,05. Upon distillation with steam Schimmel & Co.1) obtained 8,4 p. c. of an almost white volatile oil and 91,3 p. c. of a yellow, fragile resin.
Properties. Like the oil of Pinus Jeffrey!, this oil is characterized by possessing the lowest specific gravity of all volatile oils. Schimmel & Co.2) ascertained the following constants: d15O0,6962; aD - 0°9'; 5 p. c. distil over between 97 and 98,5°; 87 p. c. between 98,5 and 99°, 8 p. c. above 99°. The principal fraction of 98,5 to 99° was optically inactive; d15O0,6880; and corresponded otherwise in its -properties with those recorded by Thorpe for heptane (see below).
The portion of the oil which boiled above 99° was resolved by fractionation in vacuum into 7 fractions. Their boiling points varied between 43 and 103° under 12 mm pressure. With the exception of the last fraction, which was dextrogyrate, all of the fractions were laevogyrate. That fraction, which in its boiling point corresponded to the terpene fractions, absorbed bromine freely with slight development of hydrogen bromide. A further investigation was not undertaken.
The oil was produced for the first time in California when during the War of Secession the production of turpentine had ceased in the Southern states2). In 1868 it was brought into the San Francisco market under the names abietene, butte-tine, erasine, aurantine and theoline as a substitute for benzin for the removal of stains.
Composition. The oil was first examined by W. T. Wenzell3). He found that the bulk of the crude oil, which boiled between 101 and 105° consisted almost exclusively of a hydrocarbon sp. gr. 0,694 at 16,5° which he named abietene.
1) Report of Schimmel & Co. October 1906, 64.
2) W. T. Wenzell, Pharm. Review 22 (1904), 409.
3) Americ. Journ. Pharm. 44 (1872), 97; Chem. Zentralbl. 1872, 712. - Pharmaceutical Journ. III. 2 (1872), 789.
Abietene is not attacked by hydrochloric, sulphuric and nitric acids in the cold. According to Thorpe1) it is identical with heptane. This result was verified later by W. C. Blasdale2). The investigations of Venable3) upon heptane were not conducted, as was demonstrated later by Wenzell1), with the oil from Pinus Sabiniana, but with that of Pinus Jeffrey/.