Constitution of cannabiscitrin—Part II

Summary

The methylation of the glucoside, cannabiscitrin and of the aglucone, cannabiscetin has now been effected by a more efficient method and the fission products examined. As the result cannabiscetin has been identified as myricetin and the identity has been confirmed by comparison of the flavonol and its derivatives with synthetic samples. It is noted that the reactions of flavonols having the pyrogallol side-phenyl nucleus exhibit many similarities with those given by flavonols having the 5∶7∶8-arrangement of hydroxyl groups. The condensation of hydroxy-fisetol-trimethyl ether with the anhydride and sodium salt of gallic acid yields pentamethyl-myricetin instead of the expected hexamethyl ether, partial demethylation having taken place in the 5 position during the course of the condendation.

Methylation of the glucoside, cannabiscitrin yields a pentamethyl ether which forms on hydrolysis pentamethyl cannabiscetin (myricetin). Alkali fission of this compound gives the same ketone as the hexamethyl ether. The acid part is identified as 4∶5-dimethyl gallic acid, thus locating the position of the sugar group definitely in the 3′ position of the flavonol. This result has been confirmed by ethylating the pentamethyl cannabiscetin and subjecting the ethyl ether to fission with alkali. Besides the ketone already mentioned, the acid decomposition product is found to be 3-ethyl-4∶5-dimethyl gallic acid by comparison with a synthetic sample. The synthesis of the ethyl-dimethyl gallic acid is described.