Hydroxyl radical induced oxidation of 3-methoxy-4-hydroxy cinnamic acid (ferulic acid)

Mary Ella M. Pierpont, Galen N. Breningstall, Charles A. Stanley, Amarjit Singh

Research output: Contribution to journalArticlepeer-review

12 Scopus citations


Hydroxyl radical reaction of 3-methoxy-4-hydroxy cinnamic acid (ferulic acid) produced the ·OH-radical adducts. A part of these radical adducts undergo water elimination to finally yield phenoxyl radicals and the process was found to be base catalysed. Phenoxyl radical of ferulic acid was further identified by following its reaction with more specific oxidising radicals, e.g. azide (N3·) and Cl·2- in the pH range from 2.5 to 9. The phenoxyl radicals produced by one-electron oxidation did not possess any pKa in this pH range. The one-electron reduction potential for the formation of the phenoxyl radical was determined after achieving electron transfer equilibrium between the two couples involving the phenoxyl radical/phenol and phenothiazine radical cation/phenothiazine. Scavenging ability of the phenol toward NO·2 radical was evaluated.

Original languageEnglish (US)
Pages (from-to)519-527
Number of pages9
JournalResearch on Chemical Intermediates
Issue number4-5
StatePublished - 2001


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