Manganese peroxidase-catalyzed oxidative degradation of vanillylacetone

Sangpill Hwang, Chang Ha Lee, Ik Sung Ahn, Kwangyong Park

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

When 4-(4-hydroxy-3-methoxy-phenyl)-2-butanone (vanillylacetone) was tested for manganese peroxidase (MnP)-catalyzed oxidation, it was found to be degraded with the cleavage of an aromatic ring. Among numerous products of vanillylacetone oxidation, four major ones were purified by thin-layer chromatography and identified using mass spectroscopy (MS) and nuclear magnetic resonance (NMR) analysis. Three of them maintained the aromatic ring structure and were identified as 4-[6,2′-dihydroxy-5,3′-dimethoxy-5′-(3-oxo-butyl)-biphenyl]-butan-2-one, 4-(4-hydroxy-3-methoxyphenyl)-3-buten-2-one, and 4-[6,2′-dihydroxy-5,3′-dimethoxy-5′-(3-oxo-butyl)-biphenyl]-3-buten-2-one. Even though the fourth product could not be purified to a single compound, data from infrared spectroscopy showed that it did not have a benzene ring. From MS and NMR analysis, 3-(3-oxo-butyl)-hexa-2,4-dienedioic acid-1-methyl ester was tentatively suggested as the dominant species. The reaction mechanism was suggested on the basis of the structural information of these products. To our knowledge, this paper is the first report on aromatic ring cleavage of the phenolic compound by MnP.

Original languageEnglish
Pages (from-to)572-577
Number of pages6
JournalChemosphere
Volume72
Issue number4
DOIs
Publication statusPublished - 2008 Jun 1

Fingerprint

manganese peroxidase
Manganese
manganese
Mass Spectrometry
Magnetic Resonance Spectroscopy
Nuclear magnetic resonance
Spectroscopy
Degradation
Thin layer chromatography
Oxidation
degradation
cleavage
nuclear magnetic resonance
Thin Layer Chromatography
Benzene
spectroscopy
oxidation
Infrared spectroscopy
Spectrum Analysis
Esters

All Science Journal Classification (ASJC) codes

  • Environmental Engineering
  • Environmental Chemistry
  • Chemistry(all)
  • Pollution
  • Health, Toxicology and Mutagenesis

Cite this

Hwang, Sangpill ; Lee, Chang Ha ; Ahn, Ik Sung ; Park, Kwangyong. / Manganese peroxidase-catalyzed oxidative degradation of vanillylacetone. In: Chemosphere. 2008 ; Vol. 72, No. 4. pp. 572-577.
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Manganese peroxidase-catalyzed oxidative degradation of vanillylacetone. / Hwang, Sangpill; Lee, Chang Ha; Ahn, Ik Sung; Park, Kwangyong.

In: Chemosphere, Vol. 72, No. 4, 01.06.2008, p. 572-577.

Research output: Contribution to journalArticle

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