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Liberation of Hydrogen Sulfide from Dicysteinyl Polysulfanes in Model Wine

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journal contribution
posted on 12.12.2018, 00:00 by Marlize Z. Bekker, Gal Y. Kreitman, David W. Jeffery, John C. Danilewicz
Diorganopolysulfanes can be generated when hydrogen sulfide (H2S) and thiols are oxidized in the presence of Cu­(II) under conditions usually aimed at removing H2S from wine. This work sought to understand if polysulfanes could act as latent sources of H2S during postbottling storage. The stability of the polysulfanes formed in situ in model wine containing cysteine, H2S, and transition metals was dependent both on the number of sulfur linking atoms (Sn) and on the presence of a reducing agent, such as sulfur dioxide or ascorbic acid. A polysulfane containing three linking sulfur atoms was the most stable, with 84% of the relative initial amount remaining in solution after six months, compared to polysulfanes containing four or more linking sulfur atoms that decomposed rapidly, with 26% remaining after six months. Importantly, sulfur dioxide was associated with the rapid degradation of polysulfanes and subsequent liberation of H2S. Three cysteine-S-sulfonates were also tentatively identified, which gives insight into the possible release mechanisms involved with H2S reappearance.