Reaction mechanism of direct episulfidation of caryophyllene and humulene.
Direct episulfidations of caryophyllene or humulene with elemental sulfur were examined by means of gas chromatography. Caryophyllene-6,7-episulfide was formed at an early stage in a reaction of the caryophyllene and elemental sulfur at 120 degrees C. Caryophyllene-3,6-sulfide and polymer compounds were formed after the episulfidation. Formations of the these compounds were related to the disappearance of the caryophyllene-6,7-episulfide. Isomerization from the caryophyllene to isocaryophyllene was also observed during the reaction. In the reaction of humulene with elemental sulfur, humulene-6,7-episulfide was initially produced and then converted to humulene-9,10-episulfide. It was assumed that the polymer compound in the reaction of humulene with sulfur was related to the disappearance of the both humulene episulfides.
Ashitani
Tatsuya
T
Institute of Wood Technology, Akita Prefectural University, Noshiro 016-0876, Japan. ashitani@iwt.akita-pu.ac.jp
Borg-Karlson
Anna-Karin
AK
Fujita
Koki
K
Nagahama
Shizuo
S
D000081222:Monocyclic Sesquiterpenes; D000081223:Polycyclic Sesquiterpenes; D012717:Sesquiterpenes / Q000737:chemistry*; D013440:Sulfides / Q000138:chemical synthesis*; D013455:Sulfur / Q000737:chemistry*
D000081222:Monocyclic Sesquiterpenes; D000081223:Polycyclic Sesquiterpenes; D012717:Sesquiterpenes; D013440:Sulfides; C042686:humulene; D013455:Sulfur; C024714:caryophyllene