Chiral analysis of cis-2-methyl-4-propyl-1,3-oxathiane and identification of cis-2,4,4,6-tetramethyl-1,3-oxathiane in wine

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dc.contributor.authorWang, X.
dc.contributor.authorCapone, D.L.
dc.contributor.authorRoland, A.
dc.contributor.authorJeffery, D.W.
dc.date.issued2021
dc.descriptionAvailable online 2 March 2021
dc.description.abstractcis-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.
dc.description.statementofresponsibilityXingchen Wang, Dimitra L. Capone, Aurélie Roland, David W. Jeffery
dc.identifier.citationFood Chemistry, 2021; 357:129406-1-129406-11
dc.identifier.doi10.1016/j.foodchem.2021.129406
dc.identifier.issn0308-8146
dc.identifier.issn1873-7072
dc.identifier.orcidWang, X. [0000-0002-5001-4625]
dc.identifier.orcidCapone, D.L. [0000-0003-4424-0746]
dc.identifier.orcidJeffery, D.W. [0000-0002-7054-0374]
dc.identifier.urihttp://hdl.handle.net/2440/131606
dc.language.isoen
dc.publisherElsevier
dc.relation.granthttp://purl.org/au-research/grants/arc/IC170100008
dc.rights© 2021 Elsevier Ltd. All rights reserved.
dc.source.urihttps://doi.org/10.1016/j.foodchem.2021.129406
dc.subject3-Sulfanylhexan-1-ol; 4-Methyl-4-sulfanylpentan-2-ol; Enantiomers; Stable isotope dilution assay; Chiral analysis
dc.titleChiral analysis of cis-2-methyl-4-propyl-1,3-oxathiane and identification of cis-2,4,4,6-tetramethyl-1,3-oxathiane in wine
dc.typeJournal article
pubs.publication-statusPublished

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