Sulfane Sulfur Compounds as Source of Reappearance of Reductive Off-Odors in Wine

Reactive compounds with one or more sulfane sulfur atoms can be an important source of reductive off-odors in wine. These substances contain labile sulfur, which can participate in microbiological (enzymatic) and chemical transformations (including in the post-bottling period), releasing malodorous hydrogen sulfide (H2S) and its derivatives (MeSH, EtSH, etc.). The following sulfane sulfur compounds were considered in this review as important precursors in the wine chemistry of reductive aromas: elemental sulfur (S-8), persulfides (R-S-S-H), polysulfanes (R-S-n-R-('())), polythionates (-O3S-S-n-SO3-), thiosulfate (S2O32-) and derivatives of (poly)sulfane monosulfonic acids (R-S-n-SO3H). This review discusses the formation of these compounds, their reactivity and chemical transformations in wine, including reactions of nucleophilic substitution. In particular, the reactions of thiolysis, thiosulfatolysis and sulfitolysis of sulfane sulfur compounds are described, which lead in the end to reductive aroma compounds. In this way, the review attempts to shed light on some of the mysteries in the field of sulfur chemistry in wine and the reappearance of reductive off-odors after bottling.