New Precursors to 3-Sulfanylhexan-1-ol? Investigating the Keto–Enol Tautomerism of 3-<i>S</i>-Glutathionylhexanal
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-<i>S</i>-gluthathionylhexanal (glut-3SH-al). The biogenesis of 3SH is not fully un...
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doaj-ebd7e55de4b3413395ca01819687d87d2021-07-23T13:56:37ZengMDPI AGMolecules1420-30492021-07-01264261426110.3390/molecules26144261New Precursors to 3-Sulfanylhexan-1-ol? Investigating the Keto–Enol Tautomerism of 3-<i>S</i>-GlutathionylhexanalJennifer R. Muhl0Lisa I. Pilkington1Rebecca C. Deed2School of Chemical Sciences, The University of Auckland, Private Bag 92019, Auckland 1142, New ZealandSchool of Chemical Sciences, The University of Auckland, Private Bag 92019, Auckland 1142, New ZealandSchool of Chemical Sciences, The University of Auckland, Private Bag 92019, Auckland 1142, New ZealandThe 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-<i>S</i>-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.https://www.mdpi.com/1420-3049/26/14/42613-sulfanylhexan-1-olaroma compound precursorswhite winedeuterium exchangetautomerism |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Jennifer R. Muhl Lisa I. Pilkington Rebecca C. Deed |
spellingShingle |
Jennifer R. Muhl Lisa I. Pilkington Rebecca C. Deed New Precursors to 3-Sulfanylhexan-1-ol? Investigating the Keto–Enol Tautomerism of 3-<i>S</i>-Glutathionylhexanal Molecules 3-sulfanylhexan-1-ol aroma compound precursors white wine deuterium exchange tautomerism |
author_facet |
Jennifer R. Muhl Lisa I. Pilkington Rebecca C. Deed |
author_sort |
Jennifer R. Muhl |
title |
New Precursors to 3-Sulfanylhexan-1-ol? Investigating the Keto–Enol Tautomerism of 3-<i>S</i>-Glutathionylhexanal |
title_short |
New Precursors to 3-Sulfanylhexan-1-ol? Investigating the Keto–Enol Tautomerism of 3-<i>S</i>-Glutathionylhexanal |
title_full |
New Precursors to 3-Sulfanylhexan-1-ol? Investigating the Keto–Enol Tautomerism of 3-<i>S</i>-Glutathionylhexanal |
title_fullStr |
New Precursors to 3-Sulfanylhexan-1-ol? Investigating the Keto–Enol Tautomerism of 3-<i>S</i>-Glutathionylhexanal |
title_full_unstemmed |
New Precursors to 3-Sulfanylhexan-1-ol? Investigating the Keto–Enol Tautomerism of 3-<i>S</i>-Glutathionylhexanal |
title_sort |
new precursors to 3-sulfanylhexan-1-ol? investigating the keto–enol tautomerism of 3-<i>s</i>-glutathionylhexanal |
publisher |
MDPI AG |
series |
Molecules |
issn |
1420-3049 |
publishDate |
2021-07-01 |
description |
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-<i>S</i>-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. |
topic |
3-sulfanylhexan-1-ol aroma compound precursors white wine deuterium exchange tautomerism |
url |
https://www.mdpi.com/1420-3049/26/14/4261 |
work_keys_str_mv |
AT jenniferrmuhl newprecursorsto3sulfanylhexan1olinvestigatingtheketoenoltautomerismof3isiglutathionylhexanal AT lisaipilkington newprecursorsto3sulfanylhexan1olinvestigatingtheketoenoltautomerismof3isiglutathionylhexanal AT rebeccacdeed newprecursorsto3sulfanylhexan1olinvestigatingtheketoenoltautomerismof3isiglutathionylhexanal |
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