TY - JOUR T1 - New Precursors to 3-Sulfanylhexan-1-ol? Investigating the Keto-Enol Tautomerism of 3-S-Glutathionylhexanal. AU - Muhl,Jennifer R, AU - Pilkington,Lisa I, AU - Deed,Rebecca C, Y1 - 2021/07/14/ PY - 2021/06/14/received PY - 2021/07/09/revised PY - 2021/07/12/accepted PY - 2021/7/24/entrez PY - 2021/7/25/pubmed PY - 2021/9/18/medline KW - 3-sulfanylhexan-1-ol KW - aroma compound precursors KW - deuterium exchange KW - tautomerism KW - white wine JF - Molecules (Basel, Switzerland) JO - Molecules VL - 26 IS - 14 N2 - 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. SN - 1420-3049 UR - https://www.unboundmedicine.com/medline/citation/34299536/New_Precursors_to_3_Sulfanylhexan_1_ol_Investigating_the_Keto_Enol_Tautomerism_of_3_S_Glutathionylhexanal_ DB - PRIME DP - Unbound Medicine ER -