New Precursors to 3-Sulfanylhexan-1-ol? Investigating the Keto-Enol Tautomerism of 3-S-Glutathionylhexanal.

Jennifer R Muhl, Lisa I Pilkington, Rebecca C Deed

Molecules (Basel, Switzerland) 2021 Jul 14

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The volatile thiol compound 3-sulfanylhexan-1-ol (3SH) is a key impact odorant of white wines such as Sauvignon Blanc. 3SH is produced during fermentation by metabolism of non-volatile precursors such as 3-S-gluthathionylhexanal (glut-3SH-al). The biogenesis of 3SH is not fully understood, and the role of glut-3SH-al in this pathway is yet to be elucidated. The aldehyde functional group of glut-3SH-al is known to make this compound more reactive than other precursors to 3SH, and we are reporting for the first time that glut-3SH-al can exist in both keto and enol forms in aqueous solutions. At wine typical pH (~3.5), glut-3SH-al exists predominantly as the enol form. The dominance of the enol form over the keto form has implications in terms of potential consumption/conversion of glut-3SH-al by previously unidentified pathways. Therefore, this work will aid in the further elucidation of the role of glut-3SH-al towards 3SH formation in wine, with significant implications for the study and analysis of analogous compounds.

Citation

Jennifer R Muhl, Lisa I Pilkington, Rebecca C Deed. New Precursors to 3-Sulfanylhexan-1-ol? Investigating the Keto-Enol Tautomerism of 3-S-Glutathionylhexanal. Molecules (Basel, Switzerland). 2021 Jul 14;26(14)