Wang, X.Capone, D.L.Roland, A.Jeffery, D.W.2021-08-252021-08-252021Food Chemistry, 2021; 357:129406-1-129406-110308-81461873-7072http://hdl.handle.net/2440/131606Available online 2 March 2021cis-2-Methyl-4-propyl-1,3-oxathiane (cis-2-MPO), arising from 3-sulfanylhexan-1-ol (3-SH) and acetaldehyde, was recently identified in wine, but the enantiomeric distribution was unknown. Such information could reveal influences on wine aroma, given the impact of chirality on odorant molecules. Herein, a stable isotope dilution assay employing headspace solid-phase microextraction with chiral gas chromatography–mass spectrometry was developed, validated, and applied to a selection of wines. Studies with (3R)-3-SH revealed the elution order of the cis-2-MPO enantiomers and the concentrations of (2R,4S)-2-MPO and (2S,4R)-2-MPO in the studied wines ranged from undetected to 250 ng/L and 303 ng/L, respectively. Strong positive correlations were found between (3R)-3-SH and (2S,4R)-2-MPO (r = 0.654), and (3S)-3-SH and (2R,4S)-2-MPO (r = 0.860). Additionally, cis- 2,4,4,6-tetramethyl-1,3-oxathiane, constituted from acetaldehyde and 4-methyl-4-sulfanylpentan-2-ol (4- MSPOH), was identified in wine for the first time. This new 1,3-oxathiane, which presents a novel fate for 4- MSPOH, was detected in wines as a single enantiomer at up to 28 ng/L.en© 2021 Elsevier Ltd. All rights reserved.3-Sulfanylhexan-1-ol; 4-Methyl-4-sulfanylpentan-2-ol; Enantiomers; Stable isotope dilution assay; Chiral analysisJournal article100003840810.1016/j.foodchem.2021.1294060006555369000062-s2.0-85104420966570272Wang, X. [0000-0002-5001-4625]Capone, D.L. [0000-0003-4424-0746]Jeffery, D.W. [0000-0002-7054-0374]