Reaction mechanism of direct episulfidation of caryophyllene and humulene

Tatsuya Ashitani, Anna Karin Borg-Karlson, Koki Fujita, Shizuo Nagahama

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10 Citations (Scopus)

Abstract

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°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.

Original languageEnglish
Pages (from-to)495-498
Number of pages4
JournalNatural Product Research
Volume22
Issue number6
DOIs
Publication statusPublished - Apr 15 2008

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Biochemistry
  • Plant Science
  • Organic Chemistry

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