Reactivity on Photooxidation of Selected Five-Membered Heterocyclic Flavor Compounds

Chung Wen Chen, Chi Tang Ho

Research output: Contribution to journalArticlepeer-review

7 Scopus citations


Conjugated five-membered heterocyclic compounds including 2-ethylfuran, 2-furfural, 2-acetylfuran, 5-(hydroxymethyl)-2-furfural (HMF), 2-ethylthiophene, 2-formylthiophene, 2-acetylthiophene, 2-ethylpyrrole, 2-formylpyrrole, 2-acetylpyrrole, 2,4,5-trimethyloxazole, and 2,4,5-trimethylthiazole in absolute alcohol containing chlorophylls were bubbled with oxygen under light for 1 h. The reactivity of these heterocyclic compounds with singlet oxygen was studied using a high-performance liquid Chromatographie method, in which the percentage of substrate remaining was determined. The photooxidation reactivity of these selected five-membered flavor compounds was as follows: 2-ethylpyrrole > 2-ethylfuran > 2-ethylthiophene; 2,4,5-trimethyloxazole > 2,4,5-trimethylthiazole; 2-ethylfuran > HMF > 2-acetylfuran > 2-furfural; 2-ethylpyrrole > 2-acetylpyrrole > 2-formylpyrrole. The electron density at C-1 and C-4 may explain the photooxidation reactivity of these five-membered heterocyclic compounds.

Original languageEnglish (US)
Pages (from-to)2078-2080
Number of pages3
JournalJournal of agricultural and food chemistry
Issue number8
StatePublished - Aug 1996

All Science Journal Classification (ASJC) codes

  • Chemistry(all)
  • Agricultural and Biological Sciences(all)


  • Chlorophyll
  • Five-membered heterocyclic compounds
  • Photooxidation reactivity
  • Singlet oxygen

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