204 



A. R. PEN I- OLD. 



ground pot. permanganate, 2§ grms. caustic soda, 100 grms. 

 ice and 600 c.c. water for several hours; saturated solution 

 with 00 3 gas and steam distilled, then concentrated to 

 about 200 .c.c. volume in 0O 2 gas and extracted with 

 chloroform several times to remove impurities. On further 

 concentration and cooling the characteristic crystals of 

 sodium nopinate separated. These were pumped off and on 

 addition of dilute H 2 S0 4 crystals of the free acid separated. 

 These on purification and recrystallisation from benzene 

 formed beautiful needles melting sharply at 127° O. 



The terpenes therefore are a and /? pinene. 



Alcohol of Rose Odour, 



The constituent giving the delicate and characteristic 

 odour of citronellol to the oil was not present in sufficient 

 quantity for identification. 



It was found to be concentrated apparently in the 

 sesquiterpene fractions boiling between 123 - 130° C. at 

 10 mm. from which it was separated by shaking the latter 

 with 50% resorcin solution and subjecting this to steam 

 distillation. Not more than a couple of c.c.'s were obtained 

 in this way. It had a distinct odour of citronellol and 

 refractive index of 1*4854 at 20° O. 



It was recovered unchanged after heating on a water 

 bath for several hours with equal weight of phthalic 

 anhydride in benzene solution (proof of it not being geraniol 

 or citronellol). It did not form a phenylurethane. 



Determination of the Sesquiterpenes. 

 These were worked up from Sample 15/5/20, fraction 125 

 - 140° O. at 10 mm. This was allowed to stand over metallic 

 sodium for a week, and then repeatedly fractionated over 

 this metal at 10 mm. until about equal volumes of the 

 following fractions of constant boiling point were obtained: 



