Please use this identifier to cite or link to this item: https://hdl.handle.net/2440/116929
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Type: Journal article
Title: Reaction mechanisms of metals with hydrogen sulfide and thiols in model wine. Part 1: copper-catalyzed oxidation
Author: Kreitman, G.
Danilewicz, J.
Jeffery, D.
Elias, R.
Citation: Journal of Agricultural and Food Chemistry, 2016; 64(20):4095-4104
Publisher: American Chemical Society
Issue Date: 2016
ISSN: 0021-8561
1520-5118
Statement of
Responsibility: 
Gal Y. Kreitman, John C. Danilewicz, David. W. Jeffery and Ryan J. Elias
Abstract: Sulfidic off-odors as a result of hydrogen sulfide (H₂S) and low-molecular-weight thiols are commonly encountered in wine production. These odors are usually removed by the process of Cu(II) fining, a process that remains poorly understood. The present study aims to elucidate the underlying mechanisms by which Cu(II) interacts with H₂S and thiol compounds (RSH) under wine-like conditions. Copper complex formation was monitored along with H₂S, thiol, oxygen, and acetaldehyde concentrations after the addition of Cu(II) (50 or 100 μM) to air-saturated model wine solutions containing H₂S, cysteine, 6-sulfanylhexan-1-ol, or 3-sulfanylhexan-1-ol (300 μM each). The presence of H₂S and thiols in excess to Cu(II) led to the rapid formation of ∼1.4:1 H₂S/Cu and ∼2:1 thiol/Cu complexes, resulting in the oxidation of H₂S and thiols and reduction of Cu(II) to Cu(I), which reacted with oxygen. H₂S was observed to initially oxidize rather than form insoluble copper sulfide. The proposed reaction mechanisms provide insight into the extent to which H₂S can be selectively removed in the presence of thiols in wine.
Keywords: H₂S; thiols; copper; oxidation; wine aroma; reaction mechanism
Rights: © 2016 American Chemical Society
DOI: 10.1021/acs.jafc.6b00641
Appears in Collections:Agriculture, Food and Wine publications
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