24 OLEOKESINS OF SOME WESTEKN PINES. , 



Phettandrene. By repeated fractionation about 10 c. c. of oil boil- 

 ing between 169 and 174.5 with a specific gravity of 0.8550 was 

 obtained. When 5 c. c. were treated with bromine, no crystalline 

 derivative was obtained, indicating the absence of limonene ; with N 2 O 3 

 a copious crystalline precipitate was obtained, which, when filtered 

 with a force pump, suddenly decomposed into an amorphous mass that 

 could not again be obtained in a crystalline state. It is probable 

 that a small amount of phellandrene was present. 



Aliphatic hydrocarbon. The residue boiling above 178.8, which 

 amounted to 13.5 per cent, was distilled at 25 mm. pressure one- 

 fourth distilled between 110 and 130 and the remainder between 

 130 and 145. The portion boiling between 110 and 130 at 25 

 mm. was split up into four fractions whose specific gravities and 

 indices of refraction showed that it could not consist of -terpenes. 

 These fractions were accordingly combined and treated with concen- 

 trated sulphuric acid until no further reaction was caused by the 

 addition of more acid. The residual oil boiled between 194 and 201 

 C. at 742.7 mm.; the specific gravity was 0.7549 and the index of 

 refraction, 1.4249. The decrease in the index of refraction of the 

 tenth fraction, shown in Table 4, must be due to this oil, since all 

 terpenes of as high a boiling point have a much higher index of refrac- 

 tion. From its physical and chemical properties this oil may be a 

 hydrocarbon of the paraffin series. Owing to the small amount of 

 material available for analysis no more definite information could be 

 obtained. The results are based on analysis of material collected 

 during the years 1910 and 1911. 



Aromadendrene. The portion of the residue boiling between 130 

 and 145 at 25 mm. pressure consisted of a sesquiterpene. It did 

 not yield a crystalline derivative with Br, N 2 O 3 , or HC1. The care- 

 fully purified oil had the following properties: Boiling point, 144 to 

 148 at 30 mm. (250 to 255 at 739.9 mm.); specific gravity, 0.9238; 

 index of refraction, 1.5006; specific rotation, [a] D = +37.88 deter- 

 mined from a 33.33 per cent ethereal solution. When a few drops 

 were dissolved in glacial acetic acid in a test tube, and bromine vapors 

 were allowed to flow into the tube, a series of beautiful color reactions 

 were obtained. The solution first turned crimson, then violet, and 

 on standing 5 to 10 minutes became a deep blue. In" its physical 

 properties and color reactions the sesquiterpene from Pinus lamberti- 

 ana agrees welt with the sesquiterpene " aromadendrene," described 

 by Smith * as occurring in Australian eucalyptus oils. Aroma- 

 dendrene shows the color reactions given above, boils between 260 

 and 265 C. at atmospheric pressure, and has a specific gravity of 

 0.9229 to 0.9249 at 19 C. 



i Jour, and Proc. Roy. Soc. N. S. W., pp. 124-126, vol. 25, 1901. 



