Identification of free radical intermediates in oxidized wine using electron paramagnetic resonance spin trapping

Ryan Elias, Mogens L. Andersen, Leif H. Skibsted, Andrew L. Waterhouse

Research output: Contribution to journalArticle

69 Citations (Scopus)

Abstract

Free radicals are thought to be key Intermediates in the oxidation of wine, but their nature has not been established. Electron paramagnetic resonance spectroscopy was used to detect and identify several free radical species in wine under oxidative conditions with the aid of spin traps. The 1 -hydroxylethyl radical was the sole radical species observed when α-(4-pyridyl-1 -oxide)-N-tert-butylnitrone was used as a spin trap in a heated (55 °C), low-sulfite (15 mg L -1) red wine. This radical appears to arise from ethanol oxidation via the hydroxyl radical, and this latter species was confirmed by using a high concentration (1.5 M) of the 5,5-dimethylpyrroline-N- oxide spin trap, thus providing the first direct evidence of the Fenton reaction in wine. Hydroxyl radical formation in wine was corroborated by converting hydroxyl radicals to methyl radicals by its reaction with dimethyl sulfoxide. The novel spin trap 5-tert-butoxycarbonyl 5-methyl-1-pyrrollne /V-oxide was also used in this study to identify sulfite radicals in wine for the first time. This spin trap has also been shown to trap hydroperoxyl radicals, the generation of which is predicted in wine; however, no evidence of this species was observed.

Original languageEnglish (US)
Pages (from-to)4359-4365
Number of pages7
JournalJournal of Agricultural and Food Chemistry
Volume57
Issue number10
DOIs
StatePublished - May 27 2009

Fingerprint

Spin Trapping
Wine
electron paramagnetic resonance spectroscopy
Electron Spin Resonance Spectroscopy
Free Radicals
Paramagnetic resonance
wines
traps
Hydroxyl Radical
Oxides
hydroxyl radicals
Sulfites
oxides
sulfites
Oxidation
oxidation
Dimethyl Sulfoxide
spin trapping
dimethyl sulfoxide
red wines

All Science Journal Classification (ASJC) codes

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

Cite this

Elias, Ryan ; Andersen, Mogens L. ; Skibsted, Leif H. ; Waterhouse, Andrew L. / Identification of free radical intermediates in oxidized wine using electron paramagnetic resonance spin trapping. In: Journal of Agricultural and Food Chemistry. 2009 ; Vol. 57, No. 10. pp. 4359-4365.
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Identification of free radical intermediates in oxidized wine using electron paramagnetic resonance spin trapping. / Elias, Ryan; Andersen, Mogens L.; Skibsted, Leif H.; Waterhouse, Andrew L.

In: Journal of Agricultural and Food Chemistry, Vol. 57, No. 10, 27.05.2009, p. 4359-4365.

Research output: Contribution to journalArticle

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