THE JOURNAL OF PHARMACOLOGY. 251 



Those parts of sassafras oil which remain liquid even in a freezing mix- 

 ture, can be separated into their constituents by fractional distillation. In 

 this way a considerable fraction is obtained, boiling between 155 and 

 1 75 which consists chiefly of pinene, C x Hi 6 , that terpene which is found 

 so generally in volatile oils, and which forms the greater part of oil of tur- 

 pentine. It can be easily identified by its crystalline nitrosochloride and 

 by the easily crystallizable benzylamine and piperodine compounds of the 

 latter. Besides pipene a small amount of another terpene, C 10 H 16 , is 

 present, which forms a solid, but very unstable addition product with 

 nitrous acid, by which reaction it is recognized as phellandreue, a terpene 

 also very frequently met with in essential oils. 



The higher-boiling fractions of sassafras oil contain about 0.5 per cent, 

 of a body which can be extracted by means of a diluted solution of al- 

 kali. When set free from this solution by sulphuric acid, it forms an oil, 

 which by its clover-like odor and the formation of a benzoyl compound 

 melting at 69 C, can be identified as eugenol, the characteristic constitu- 

 ent of oil of cloves. Eugenol, C 10 H 12 O 2 , is distinguished from safrol 

 only by possessing two additional atoms of hydrogen in its empirical 

 formula. In its structural composition it is also closely allied to the latter, 

 being the methylic instead of the methylenic ether of the same phenol : 



CH.,=CH.CH 2 

 C 



HC J I CH 



CO.CH, 



HO— C 



We therefore are led to suppose that safrol and eugenol are generated in 

 the plant by nearly allied processes.. Those fractions of sassafras oil 

 which boil in the neighborhood of 200 C, upon cooling yield an abun- 

 dance of colorless prisms, which, after proper purification, can be recog- 

 nized as common dextro-camphor, C 10 H 29 O, by their melting point, odor, 

 optical rotation and the formation of a well crystallizing oxime melting at 

 115 . In one authentic specimen of sassafras oil as much as 6.8 per cent, 

 of camphor has been found by reduction of the camphor to borneol, 

 C 10 H 18 O, acetylizing the latter with acetic anhydride and saponifying a 

 weighed amount of the acetylized oil. 



The highest boiling fractions of the oil seem to contain a small amount 

 of a sesquiterpene, C 15 H 24 , according to certain color reactions apparently 

 cardinene, the presence of which, however, has not yet been proven be- 

 yond all doubt. 



The composition of oil of sassafras bark may therefore be summarized 

 as follows : 



