— 94 — 



Fraction No. 1 (b. p. 50°-100°C. under 15 mm pressure). The fraction 

 is mobile, colorless and has a somewhat lemon-like smell. When purified 

 by repeated distillation over sodium under diminished pressure and finally 

 under atmospheric pressure, it boils mostly at 161°-165°C. and is proved to 

 be identical vsrith a-pinen by the nitrosochloride (m. p. 102°-103°), the 

 nitrolpiperidine (m. p. 118°-190°) and nitrolbenzylamine (m. p. 122°-123°). 



Fraction No. 2 (b. p. 100°-180°C. under 15 mm pressure). This frac- 

 tion, after hydrolysing with 5% alcoholic potash, was distilled under 

 atmospheric pressure and was separated into 4 fractions having the range 

 of boiling point 195°-235°, 235°-280°, 280°-310°, 310°-330°. From these 

 fractions, there were detected an alcohol (CjoHigO.b.p. 212-214, N^= 1.4832), 

 a dihydrochloric sesquiterpene (C15H24; b. p. 266°-268°,M = + 15.19 in a 6% 

 chloroform solution, d„=0.9335, Ng-«=1.5041), Cadinene (C^sH^; b.p. 272) 

 and a sesquiterpene alcohol (CwHsoO; b. p. 284°-286°; d:B.5=0.9623, (a]f= 

 + 16.76 in 5% chloroform solution, N^^-8= 1.5048). 



Fraction No. 3 (b. p. 180°-200°C. under 15 mm pressure) . This frac- 

 tion was a very viscous oil of a yellowish color which solidified on cooling 

 to a hard mass. When recrystallised from acetic ether, white lustrous 

 needle crystals were obtained. By combustion and the determination of 

 molecular weight, the substance was proved to be a new diterpene C20H23 

 (m.p. 61°C; b. p.7eo 345°C ; b.p.i5l98°; [a]^D°=-34.22° in a 4.7% chloroform 

 solution), for which the author ventures to propose the name a-cryptomerene 

 to show its derivation from the Cryptomeria japonica. 



Also, from the alkaline liquid gained by hydrolysis of the fraction 

 (100°-180°C. 15 mm), a lactone (C^oHs^O.) and caprylic acid ('CjHsCOOH) 

 were detected but they were exceedingly small in amount. The relative 

 proportion of the constituents is approximately as follows: — 



Free acid (as acetic acid) 0.1% 



Free alcohol (as CioHigO) 3.14% 



Ester (as caprylic ester of doHisO) 3.28% 



Terpen (chiely a-pinnen) about 34% 



Sesquiterpen (cadinen and a sesquiterpen) about 30% 



A sesquiterpen alcohol (dsHjeO) 12% 



Crystalline diterpene (a-cryptomerene) about 18% 



