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Type: Journal article
Title: Reaction mechanisms of metals with hydrogen sulfide and thiols in model wine. Part 2: iron- and copper-catalyzed oxidation
Author: Kreitman, G.
Danilewicz, J.
Jeffery, D.
Elias, R.
Citation: Journal of Agricultural and Food Chemistry, 2016; 64(20):4105-4113
Publisher: American Chemical Society
Issue Date: 2016
ISSN: 0021-8561
Statement of
Gal Y. Kreitman, John C. Danilewicz, David. W. Jeffery and Ryan J. Elias
Abstract: Sulfidic off-odors arising during wine production are frequently removed by Cu(II) fining. In part 1 of this study ( 10.1021/acs.jafc.6b00641 ), the reaction of H₂S and thiols with Cu(II) was examined; however, the interaction of iron and copper is also known to play an important synergistic role in mediating non-enzymatic wine oxidation. The interaction of these two metals in the oxidation of H₂S and thiols (cysteine, 3-sulfanylhexan-1-ol, and 6-sulfanylhexan-1-ol) was therefore examined under wine-like conditions. H₂S and thiols (300 μM) were reacted with Fe(III) (100 or 200 μM) alone and in combination with Cu(II) (25 or 50 μM), and concentrations of H₂S and thiols, oxygen, and acetaldehyde were monitored over time. H₂S and thiols were shown to be slowly oxidized in the presence of Fe(III) alone and were not bound to Fe(III) under model wine conditions. However, Cu(II) added to model wine containing Fe(III) was quickly reduced by H₂S and thiols to form Cu(I) complexes, which then rapidly reduced Fe(III) to Fe(II). Oxidation of Fe(II) in the presence of oxygen regenerated Fe(III) and completed the iron redox cycle. In addition, sulfur-derived oxidation products were observed, and the formation of organic polysulfanes was demonstrated.
Keywords: H₂S; thiols; copper; iron; oxidation; wine aroma; reaction mechanism
Rights: © 2016 American Chemical Society
DOI: 10.1021/acs.jafc.6b00642
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Appears in Collections:Agriculture, Food and Wine publications
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