26 



OLEOKESINS OF SOME WESTERN PINES. 



EXAMINATION OF THE VOLATILE OIL. 



PHYSICAL PROPERTIES. 



The original oil from the oleoresin collected during the summer of 

 1911 had the following properties: Specific gravity, 0.8518; index of 

 refraction, 1 .4862 ; specific rotation, [a] D =20.12. The oil examined 

 from oleoresin collected in 1910 had: Specific gravity, 0.8549; index 

 of refraction, 1.4860. About 400 grams of the latter oil were sub- 

 mitted to fractional distillation with the results shown in Table 5. 



TABLE 5. -^-Fractional distillation of the volatile oil from Pinus contorta. 



The oil had a very characteristic odor; it was pungent when freshly 

 distilled and, after standing some time, was orange-like. The oil 

 polymerized very considerably at its boiling point. The 15 per cent 

 residue remaining in the distilling flask solidified to a solid, amber- 

 colored mass resembling colophony, insoluble in alcohol, but soluble 

 in ether and chloroform. To avoid loss of oil by polymerization it 

 must be distilled under reduced pressure. The oil carefully purified 

 and finally distilled over metallic sodium, had the following properties : 



21 



Boiling point, 60 at 11 mm.; specific gravity, 0.8460; refrac- 



15 



tive index, 1.4861; specific rotation, [a] D = -12.36. 



IDENTIFICATION OF CONSTITUENTS. 



a-pinene. The first fraction was redistilled over metallic sodium 

 and tested for or-pinene by treatment with ethyl nitrite and hydro- 

 chloric acid. No crystalline nitrosochloride or blue coloration was 

 obtained; however, the failure to secure a precipitate is not conclu- 

 sive proof of the absence of a-pinene, 1 especially when the oil is 

 highly active. 2 



Phellandrene. The ease with which the oil polymerized, and its 

 physical properties, pointed to phellandrene. When the original 

 oil was treated with potassium nitrite and acetic acid, or when any 



i Wallach: Annalen, p. 6, vol. 368, 1909. 



* Tilden: Jour. Chem. Soc., p. 759, vol. 85, 1904; also Kremers: Pharm. Rundschau, p. 135, vol. 13, 1895. 



