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Elucidation of the 1,3-sulfanylalcohol oxidation mechanism: an unusual identification of the disulfide of 3-sulfanylhexanol in sauternes botrytized wines.
J Agric Food Chem. 2010 Oct 13; 58(19):10606-13.JA

Abstract

A four-step purification method was developed to isolate a citrus odorant detected by gas chromatography-olfactometry (GC-O), which was apparently specific to Sauternes botrytized wines. A fragmentation pattern of the odorant was obtained by multidimensional gas chromatography-mass spectrometry-olfactometry (MDGC-MS-O). The exact mass measurement was used to determine its elemental formula as C(6)H(12)OS. On the basis of these data, the unusual structure of 3-propyl-1,2-oxathiolane was synthesized and characterized for the first time. This confirmed its identification. Its occurrence in Sauternes wine extracts was demonstrated to result from the thermal oxidative degradation of 3-sulfanylhexanol disulfide (3,3'-disulfanediyldihexan-1-ol) in the GC injector. This disulfide was synthesized and then firmly identified for the first time in Sauternes wine. Although the presence of 3-sulfanylhexanol oxidation products had previously been reported in natural extracts (but not wine), the full oxidation pathway from 3-sulfanylhexanol to 3-propyl-γ-sultine via 3,3'-disulfanediyldihexan-1-ol was clearly established for the first time. Because the disulfide has mainly been detected in Sauternes botrytized wines, this finding suggested a singular reactivity of 3-sulfanylhexanol in botrytized wines, thus opening up a wide range of new opportunities in wine chemistry.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Sarrazin E
UMR INRA 1219 Œnologie, Institut des Sciences de la Vigne et du Vin, Université Victor Segalen Bordeaux II, 210 Chemin de Leysotte, CS 5008, F-33882 Villenave d'Ornon, France. elise.sarrazin@unice.fr
Shinkaruk S
No affiliation info available
Pons M
No affiliation info available
Thibon C
No affiliation info available
Bennetau B
No affiliation info available
Darriet P
No affiliation info available

MeSH

Chromatography, GasDisulfidesGas Chromatography-Mass SpectrometryHexanolsHot TemperatureOdorantsOxidation-ReductionSmellSulfhydryl CompoundsWine

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

20857980

Citation

Sarrazin, Elise, et al. "Elucidation of the 1,3-sulfanylalcohol Oxidation Mechanism: an Unusual Identification of the Disulfide of 3-sulfanylhexanol in Sauternes Botrytized Wines." Journal of Agricultural and Food Chemistry, vol. 58, no. 19, 2010, pp. 10606-13.
Sarrazin E, Shinkaruk S, Pons M, et al. Elucidation of the 1,3-sulfanylalcohol oxidation mechanism: an unusual identification of the disulfide of 3-sulfanylhexanol in sauternes botrytized wines. J Agric Food Chem. 2010;58(19):10606-13.
Sarrazin, E., Shinkaruk, S., Pons, M., Thibon, C., Bennetau, B., & Darriet, P. (2010). Elucidation of the 1,3-sulfanylalcohol oxidation mechanism: an unusual identification of the disulfide of 3-sulfanylhexanol in sauternes botrytized wines. Journal of Agricultural and Food Chemistry, 58(19), 10606-13. https://doi.org/10.1021/jf102022s
Sarrazin E, et al. Elucidation of the 1,3-sulfanylalcohol Oxidation Mechanism: an Unusual Identification of the Disulfide of 3-sulfanylhexanol in Sauternes Botrytized Wines. J Agric Food Chem. 2010 Oct 13;58(19):10606-13. PubMed PMID: 20857980.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Elucidation of the 1,3-sulfanylalcohol oxidation mechanism: an unusual identification of the disulfide of 3-sulfanylhexanol in sauternes botrytized wines. AU - Sarrazin,Elise, AU - Shinkaruk,Svitlana, AU - Pons,Monique, AU - Thibon,Cecile, AU - Bennetau,Bernard, AU - Darriet,Philippe, PY - 2010/9/23/entrez PY - 2010/9/23/pubmed PY - 2011/2/4/medline SP - 10606 EP - 13 JF - Journal of agricultural and food chemistry JO - J Agric Food Chem VL - 58 IS - 19 N2 - A four-step purification method was developed to isolate a citrus odorant detected by gas chromatography-olfactometry (GC-O), which was apparently specific to Sauternes botrytized wines. A fragmentation pattern of the odorant was obtained by multidimensional gas chromatography-mass spectrometry-olfactometry (MDGC-MS-O). The exact mass measurement was used to determine its elemental formula as C(6)H(12)OS. On the basis of these data, the unusual structure of 3-propyl-1,2-oxathiolane was synthesized and characterized for the first time. This confirmed its identification. Its occurrence in Sauternes wine extracts was demonstrated to result from the thermal oxidative degradation of 3-sulfanylhexanol disulfide (3,3'-disulfanediyldihexan-1-ol) in the GC injector. This disulfide was synthesized and then firmly identified for the first time in Sauternes wine. Although the presence of 3-sulfanylhexanol oxidation products had previously been reported in natural extracts (but not wine), the full oxidation pathway from 3-sulfanylhexanol to 3-propyl-γ-sultine via 3,3'-disulfanediyldihexan-1-ol was clearly established for the first time. Because the disulfide has mainly been detected in Sauternes botrytized wines, this finding suggested a singular reactivity of 3-sulfanylhexanol in botrytized wines, thus opening up a wide range of new opportunities in wine chemistry. SN - 1520-5118 UR - https://www.unboundmedicine.com/medline/citation/20857980/Elucidation_of_the_13_sulfanylalcohol_oxidation_mechanism:_an_unusual_identification_of_the_disulfide_of_3_sulfanylhexanol_in_sauternes_botrytized_wines_ L2 - https://doi.org/10.1021/jf102022s DB - PRIME DP - Unbound Medicine ER -