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

11 Scopus citations

Abstract

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
Volume27
Issue number4-5
DOIs
StatePublished - 2001

Fingerprint Dive into the research topics of 'Hydroxyl radical induced oxidation of 3-methoxy-4-hydroxy cinnamic acid (ferulic acid)'. Together they form a unique fingerprint.

Cite this