Elucidation of the 1,3-Sulfanylalcohol Oxidation Mechanism: An Unusual Identification of the Disulfide of 3-Sulfanylhexanol in Sauternes Botrytized Wines
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−olfa...
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| Veröffentlicht in: | Journal of agricultural and food chemistry 2010-10, Vol.58 (19), p.10606-10613 |
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| container_title | Journal of agricultural and food chemistry |
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| creator | Sarrazin, Elise Shinkaruk, Svitlana Pons, Monique Thibon, Cecile Bennetau, Bernard Darriet, Philippe |
| description | 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 C6H12OS. 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. |
| doi_str_mv | 10.1021/jf102022s |
| format | Article |
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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 C6H12OS. 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.</description><identifier>ISSN: 0021-8561</identifier><identifier>EISSN: 1520-5118</identifier><identifier>DOI: 10.1021/jf102022s</identifier><identifier>PMID: 20857980</identifier><identifier>CODEN: JAFCAU</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>3-sulfanylhexanol ; biochemical pathways ; Biological and medical sciences ; Botrytis cinerea ; Botrytized wines ; Chemical and Process Engineering ; chemical reactions ; chemical structure ; Chromatography, Gas ; dessert wines ; disulfide bonds ; Disulfides - analysis ; Engineering Sciences ; Fermented food industries ; Flavors and Aromas/Chemosensory Perception ; Food engineering ; Food industries ; Fundamental and applied biological sciences. Psychology ; gas chromatography ; Gas Chromatography-Mass Spectrometry ; Hexanols - analysis ; Hexanols - chemistry ; Hot Temperature ; Life Sciences ; mass spectrometry ; molecular weight ; odor compounds ; Odorants - analysis ; odors ; olfactometry ; oxidation ; Oxidation-Reduction ; reaction pathways ; Smell ; Sulfhydryl Compounds - analysis ; Sulfhydryl Compounds - chemistry ; synthesis ; thermal degradation ; Wine - analysis ; Wines and vinegars</subject><ispartof>Journal of agricultural and food chemistry, 2010-10, Vol.58 (19), p.10606-10613</ispartof><rights>Copyright © 2010 American Chemical Society</rights><rights>2015 INIST-CNRS</rights><rights>Distributed under a Creative Commons Attribution 4.0 International License</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a468t-646af32a6c77f5230ea16d488d2de4dd45daa37929b78f14cc4370d28760dd673</citedby><cites>FETCH-LOGICAL-a468t-646af32a6c77f5230ea16d488d2de4dd45daa37929b78f14cc4370d28760dd673</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jf102022s$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jf102022s$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>230,314,777,781,882,2752,27057,27905,27906,56719,56769</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=23325327$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/20857980$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink><backlink>$$Uhttps://hal.inrae.fr/hal-02657735$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Sarrazin, Elise</creatorcontrib><creatorcontrib>Shinkaruk, Svitlana</creatorcontrib><creatorcontrib>Pons, Monique</creatorcontrib><creatorcontrib>Thibon, Cecile</creatorcontrib><creatorcontrib>Bennetau, Bernard</creatorcontrib><creatorcontrib>Darriet, Philippe</creatorcontrib><title>Elucidation of the 1,3-Sulfanylalcohol Oxidation Mechanism: An Unusual Identification of the Disulfide of 3-Sulfanylhexanol in Sauternes Botrytized Wines</title><title>Journal of agricultural and food chemistry</title><addtitle>J. Agric. Food Chem</addtitle><description>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 C6H12OS. 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.</description><subject>3-sulfanylhexanol</subject><subject>biochemical pathways</subject><subject>Biological and medical sciences</subject><subject>Botrytis cinerea</subject><subject>Botrytized wines</subject><subject>Chemical and Process Engineering</subject><subject>chemical reactions</subject><subject>chemical structure</subject><subject>Chromatography, Gas</subject><subject>dessert wines</subject><subject>disulfide bonds</subject><subject>Disulfides - analysis</subject><subject>Engineering Sciences</subject><subject>Fermented food industries</subject><subject>Flavors and Aromas/Chemosensory Perception</subject><subject>Food engineering</subject><subject>Food industries</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>gas chromatography</subject><subject>Gas Chromatography-Mass Spectrometry</subject><subject>Hexanols - analysis</subject><subject>Hexanols - chemistry</subject><subject>Hot Temperature</subject><subject>Life Sciences</subject><subject>mass spectrometry</subject><subject>molecular weight</subject><subject>odor compounds</subject><subject>Odorants - analysis</subject><subject>odors</subject><subject>olfactometry</subject><subject>oxidation</subject><subject>Oxidation-Reduction</subject><subject>reaction pathways</subject><subject>Smell</subject><subject>Sulfhydryl Compounds - analysis</subject><subject>Sulfhydryl Compounds - chemistry</subject><subject>synthesis</subject><subject>thermal degradation</subject><subject>Wine - analysis</subject><subject>Wines and vinegars</subject><issn>0021-8561</issn><issn>1520-5118</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2010</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkctuEzEUhi0EoqGw4AVgNgghMeDLeOywC6XQSkFdhIildeoLceTY7XgGNbwJb4tHSROQWB3r96dPPv4Rek7wO4Ipeb92ZWBK8wM0IZzimhMiH6IJLpe15C05QU9yXmOMJRf4MTqh42Eq8QT9Pg-D9gZ6n2KVXNWvbEXesnoxBAdxGyDotEqhurq7h75avYLo8-ZDNYvVMg55gFBdGht777z-x_TJ5-Lxxo7BUbqydxCL1MdqAUNvu2hz9TH13bb3v6ypvvsSPEWPHIRsn-3nKVp-Pv92dlHPr75cns3mNTSt7Ou2acExCq0WwnHKsAXSmkZKQ41tjGm4AWBiSqfXQjrSaN0wgQ2VosXGtIKdojc77wqCuun8BrqtSuDVxWyuxgzTlgvB-E9S2Nc79qZLt4PNvdr4rG0IEG0ashJcECE4I0er7lLOnXUHNcFqLE0dSivsi711uN5YcyDvWyrAqz0AWUNwHUTt85FjjHJGx1Ve7jgHScGPrjDLBcWEYSKnLaV_mUBntU5DF8vX_udJfwCivbRn</recordid><startdate>20101013</startdate><enddate>20101013</enddate><creator>Sarrazin, Elise</creator><creator>Shinkaruk, Svitlana</creator><creator>Pons, Monique</creator><creator>Thibon, Cecile</creator><creator>Bennetau, Bernard</creator><creator>Darriet, Philippe</creator><general>American Chemical Society</general><scope>FBQ</scope><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>1XC</scope></search><sort><creationdate>20101013</creationdate><title>Elucidation of the 1,3-Sulfanylalcohol Oxidation Mechanism: An Unusual Identification of the Disulfide of 3-Sulfanylhexanol in Sauternes Botrytized Wines</title><author>Sarrazin, Elise ; Shinkaruk, Svitlana ; Pons, Monique ; Thibon, Cecile ; Bennetau, Bernard ; Darriet, Philippe</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a468t-646af32a6c77f5230ea16d488d2de4dd45daa37929b78f14cc4370d28760dd673</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2010</creationdate><topic>3-sulfanylhexanol</topic><topic>biochemical pathways</topic><topic>Biological and medical sciences</topic><topic>Botrytis cinerea</topic><topic>Botrytized wines</topic><topic>Chemical and Process Engineering</topic><topic>chemical reactions</topic><topic>chemical structure</topic><topic>Chromatography, Gas</topic><topic>dessert wines</topic><topic>disulfide bonds</topic><topic>Disulfides - analysis</topic><topic>Engineering Sciences</topic><topic>Fermented food industries</topic><topic>Flavors and Aromas/Chemosensory Perception</topic><topic>Food engineering</topic><topic>Food industries</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>gas chromatography</topic><topic>Gas Chromatography-Mass Spectrometry</topic><topic>Hexanols - analysis</topic><topic>Hexanols - chemistry</topic><topic>Hot Temperature</topic><topic>Life Sciences</topic><topic>mass spectrometry</topic><topic>molecular weight</topic><topic>odor compounds</topic><topic>Odorants - analysis</topic><topic>odors</topic><topic>olfactometry</topic><topic>oxidation</topic><topic>Oxidation-Reduction</topic><topic>reaction pathways</topic><topic>Smell</topic><topic>Sulfhydryl Compounds - analysis</topic><topic>Sulfhydryl Compounds - chemistry</topic><topic>synthesis</topic><topic>thermal degradation</topic><topic>Wine - analysis</topic><topic>Wines and vinegars</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Sarrazin, Elise</creatorcontrib><creatorcontrib>Shinkaruk, Svitlana</creatorcontrib><creatorcontrib>Pons, Monique</creatorcontrib><creatorcontrib>Thibon, Cecile</creatorcontrib><creatorcontrib>Bennetau, Bernard</creatorcontrib><creatorcontrib>Darriet, Philippe</creatorcontrib><collection>AGRIS</collection><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>Hyper Article en Ligne (HAL)</collection><jtitle>Journal of agricultural and food chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Sarrazin, Elise</au><au>Shinkaruk, Svitlana</au><au>Pons, Monique</au><au>Thibon, Cecile</au><au>Bennetau, Bernard</au><au>Darriet, Philippe</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Elucidation of the 1,3-Sulfanylalcohol Oxidation Mechanism: An Unusual Identification of the Disulfide of 3-Sulfanylhexanol in Sauternes Botrytized Wines</atitle><jtitle>Journal of agricultural and food chemistry</jtitle><addtitle>J. Agric. Food Chem</addtitle><date>2010-10-13</date><risdate>2010</risdate><volume>58</volume><issue>19</issue><spage>10606</spage><epage>10613</epage><pages>10606-10613</pages><issn>0021-8561</issn><eissn>1520-5118</eissn><coden>JAFCAU</coden><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 C6H12OS. 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.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>20857980</pmid><doi>10.1021/jf102022s</doi><tpages>8</tpages></addata></record> |
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| subjects | 3-sulfanylhexanol biochemical pathways Biological and medical sciences Botrytis cinerea Botrytized wines Chemical and Process Engineering chemical reactions chemical structure Chromatography, Gas dessert wines disulfide bonds Disulfides - analysis Engineering Sciences Fermented food industries Flavors and Aromas/Chemosensory Perception Food engineering Food industries Fundamental and applied biological sciences. Psychology gas chromatography Gas Chromatography-Mass Spectrometry Hexanols - analysis Hexanols - chemistry Hot Temperature Life Sciences mass spectrometry molecular weight odor compounds Odorants - analysis odors olfactometry oxidation Oxidation-Reduction reaction pathways Smell Sulfhydryl Compounds - analysis Sulfhydryl Compounds - chemistry synthesis thermal degradation Wine - analysis Wines and vinegars |
| title | Elucidation of the 1,3-Sulfanylalcohol Oxidation Mechanism: An Unusual Identification of the Disulfide of 3-Sulfanylhexanol in Sauternes Botrytized Wines |
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