Reaction Mechanisms of Metals with Hydrogen Sulfide and Thiols in Model Wine. Part 2

Iron- and Copper-Catalyzed Oxidation

Gal Y. Kreitman, John C. Danilewicz, David W. Jeffery, Ryan Elias

Research output: Contribution to journalArticle

20 Citations (Scopus)

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.

Original languageEnglish (US)
Pages (from-to)4105-4113
Number of pages9
JournalJournal of Agricultural and Food Chemistry
Volume64
Issue number20
DOIs
StatePublished - May 25 2016

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Hydrogen Sulfide
reaction mechanisms
Wine
hydrogen sulfide
thiols
Sulfhydryl Compounds
wines
Copper
Iron
copper
Metals
metals
oxidation
iron
Oxidation
Oxygen
oxygen
off odors
Acetaldehyde
acetaldehyde

All Science Journal Classification (ASJC) codes

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

Cite this

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title = "Reaction Mechanisms of Metals with Hydrogen Sulfide and Thiols in Model Wine. Part 2: Iron- and Copper-Catalyzed Oxidation",
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.",
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Reaction Mechanisms of Metals with Hydrogen Sulfide and Thiols in Model Wine. Part 2 : Iron- and Copper-Catalyzed Oxidation. / Kreitman, Gal Y.; Danilewicz, John C.; Jeffery, David W.; Elias, Ryan.

In: Journal of Agricultural and Food Chemistry, Vol. 64, No. 20, 25.05.2016, p. 4105-4113.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Reaction Mechanisms of Metals with Hydrogen Sulfide and Thiols in Model Wine. Part 2

T2 - Iron- and Copper-Catalyzed Oxidation

AU - Kreitman, Gal Y.

AU - Danilewicz, John C.

AU - Jeffery, David W.

AU - Elias, Ryan

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AB - 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.

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