Evolution of Castalagin and Vescalagin in Ethanol Solutions. Identification of New Derivatives
Brandies, cognac, armagnac, whiskeys, and rums are aged in oak barrels to improve their organoleptic properties. During this period, numerous compounds such as ellagitannins are extracted from the wood and can subsequently be transformed into new derivatives by chemical reactions. Model solutions of...
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| Veröffentlicht in: | Journal of agricultural and food chemistry 1999-05, Vol.47 (5), p.2060-2066 |
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| container_end_page | 2066 |
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| container_issue | 5 |
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| container_title | Journal of agricultural and food chemistry |
| container_volume | 47 |
| creator | Puech, Jean-Louis Mertz, Christian Michon, Véronique Le Guernevé, Christine Doco, Thierry Hervé du Penhoat, Catherine |
| description | Brandies, cognac, armagnac, whiskeys, and rums are aged in oak barrels to improve their organoleptic properties. During this period, numerous compounds such as ellagitannins are extracted from the wood and can subsequently be transformed into new derivatives by chemical reactions. Model solutions of castalagin and vescalagin have been studied to determine the behavior of polyphenols in ethanol−water. Upon prolonged exposure to 40 and 70% (v/v) ethanol at room temperature, hemiketal derivatives containing ethoxy groups have been characterized by LC/MS and NMR. These compounds further evolve to afford the corresponding ketals. They have also been detected in the extracts of oak wood stored under similar conditions. Keywords: Oak wood; ellagitannins; ethanol; derivatives; HPLC; LC/MS; NMR |
| doi_str_mv | 10.1021/jf9813586 |
| format | Article |
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These compounds further evolve to afford the corresponding ketals. They have also been detected in the extracts of oak wood stored under similar conditions. Keywords: Oak wood; ellagitannins; ethanol; derivatives; HPLC; LC/MS; NMR</description><identifier>ISSN: 0021-8561</identifier><identifier>EISSN: 1520-5118</identifier><identifier>DOI: 10.1021/jf9813586</identifier><identifier>PMID: 10552496</identifier><identifier>CODEN: JAFCAU</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Alcoholic Beverages ; Antihypertensive Agents - chemistry ; Biological and medical sciences ; Biphenyl Compounds ; Brandies, spirituous liquors ; Catechols - chemistry ; chemical reactions ; chemical structure ; Chromatography, High Pressure Liquid ; containers ; derivatives ; elagitannins ; Ethanol ; ethoxylation ; Fermented food industries ; Food Handling ; Food industries ; Fundamental and applied biological sciences. Psychology ; Hydrolyzable Tannins ; Molecular Conformation ; Molecular Structure ; oak barrels ; oxidation ; polyphenols ; Quercus robur ; release ; solubility ; Solutions ; spectral analysis ; tannins ; Tannins - chemistry ; Tannins - isolation & purification ; Wood</subject><ispartof>Journal of agricultural and food chemistry, 1999-05, Vol.47 (5), p.2060-2066</ispartof><rights>Copyright © 1999 American Chemical Society</rights><rights>1999 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-a436t-81e8273e2390dafa4ce986153b8424258b7c22052a5040c3b913040f557673af3</citedby><cites>FETCH-LOGICAL-a436t-81e8273e2390dafa4ce986153b8424258b7c22052a5040c3b913040f557673af3</cites><orcidid>0000-0002-1453-8683</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jf9813586$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jf9813586$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>230,314,780,784,885,2763,27075,27923,27924,56737,56787</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=1989400$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/10552496$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink><backlink>$$Uhttps://hal.science/hal-00309791$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Puech, Jean-Louis</creatorcontrib><creatorcontrib>Mertz, Christian</creatorcontrib><creatorcontrib>Michon, Véronique</creatorcontrib><creatorcontrib>Le Guernevé, Christine</creatorcontrib><creatorcontrib>Doco, Thierry</creatorcontrib><creatorcontrib>Hervé du Penhoat, Catherine</creatorcontrib><title>Evolution of Castalagin and Vescalagin in Ethanol Solutions. Identification of New Derivatives</title><title>Journal of agricultural and food chemistry</title><addtitle>J. Agric. Food Chem</addtitle><description>Brandies, cognac, armagnac, whiskeys, and rums are aged in oak barrels to improve their organoleptic properties. During this period, numerous compounds such as ellagitannins are extracted from the wood and can subsequently be transformed into new derivatives by chemical reactions. Model solutions of castalagin and vescalagin have been studied to determine the behavior of polyphenols in ethanol−water. Upon prolonged exposure to 40 and 70% (v/v) ethanol at room temperature, hemiketal derivatives containing ethoxy groups have been characterized by LC/MS and NMR. These compounds further evolve to afford the corresponding ketals. They have also been detected in the extracts of oak wood stored under similar conditions. Keywords: Oak wood; ellagitannins; ethanol; derivatives; HPLC; LC/MS; NMR</description><subject>Alcoholic Beverages</subject><subject>Antihypertensive Agents - chemistry</subject><subject>Biological and medical sciences</subject><subject>Biphenyl Compounds</subject><subject>Brandies, spirituous liquors</subject><subject>Catechols - chemistry</subject><subject>chemical reactions</subject><subject>chemical structure</subject><subject>Chromatography, High Pressure Liquid</subject><subject>containers</subject><subject>derivatives</subject><subject>elagitannins</subject><subject>Ethanol</subject><subject>ethoxylation</subject><subject>Fermented food industries</subject><subject>Food Handling</subject><subject>Food industries</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Hydrolyzable Tannins</subject><subject>Molecular Conformation</subject><subject>Molecular Structure</subject><subject>oak barrels</subject><subject>oxidation</subject><subject>polyphenols</subject><subject>Quercus robur</subject><subject>release</subject><subject>solubility</subject><subject>Solutions</subject><subject>spectral analysis</subject><subject>tannins</subject><subject>Tannins - chemistry</subject><subject>Tannins - isolation & purification</subject><subject>Wood</subject><issn>0021-8561</issn><issn>1520-5118</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1999</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkc1uEzEUhS0EoiGw4AVgFoDEYop_xmN7WUKgRVEBpa1YYd04duswGRd7JsDb42iGlAWSJdv3fvfI5xihpwQfE0zJm41TkjAu63toQjjFJSdE3kcTnJul5DU5Qo9S2mCMJRf4IToimHNaqXqCvs13oek7H9oiuGIGqYMGrn1bQLsurmwy4zWveXcDbWiK5TiQjouztW0777yBvwrn9mfxzka_y5WdTY_RAwdNsk_GfYou388vZqfl4tOHs9nJooSK1V0piZVUMEuZwmtwUBmrZE04W8mKVpTLlTCUYk6B4wobtlKE5YPjXNSCgWNT9HrQvYFG30a_hfhbB_D69GSh9zWMGVZCkR3J7KuBvY3hR29Tp7c-Gds00NrQJ10rKmpO-Z2oiSGlaN1BmWC9D14fgs_ss1G0X23t-h9ySDoDL0YA9qG6CK3x6Y5TUlX5kVNUDphPnf11aEP8rrNTwfXF56WWX5h4e_71o77K_POBdxA0XMcsebmkOMdDFaPZciZeDgSYpDehj23-iP84-AOYa6vy</recordid><startdate>19990501</startdate><enddate>19990501</enddate><creator>Puech, Jean-Louis</creator><creator>Mertz, Christian</creator><creator>Michon, Véronique</creator><creator>Le Guernevé, Christine</creator><creator>Doco, Thierry</creator><creator>Hervé du Penhoat, Catherine</creator><general>American Chemical Society</general><scope>FBQ</scope><scope>BSCLL</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><orcidid>https://orcid.org/0000-0002-1453-8683</orcidid></search><sort><creationdate>19990501</creationdate><title>Evolution of Castalagin and Vescalagin in Ethanol Solutions. Identification of New Derivatives</title><author>Puech, Jean-Louis ; Mertz, Christian ; Michon, Véronique ; Le Guernevé, Christine ; Doco, Thierry ; Hervé du Penhoat, Catherine</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a436t-81e8273e2390dafa4ce986153b8424258b7c22052a5040c3b913040f557673af3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1999</creationdate><topic>Alcoholic Beverages</topic><topic>Antihypertensive Agents - chemistry</topic><topic>Biological and medical sciences</topic><topic>Biphenyl Compounds</topic><topic>Brandies, spirituous liquors</topic><topic>Catechols - chemistry</topic><topic>chemical reactions</topic><topic>chemical structure</topic><topic>Chromatography, High Pressure Liquid</topic><topic>containers</topic><topic>derivatives</topic><topic>elagitannins</topic><topic>Ethanol</topic><topic>ethoxylation</topic><topic>Fermented food industries</topic><topic>Food Handling</topic><topic>Food industries</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Hydrolyzable Tannins</topic><topic>Molecular Conformation</topic><topic>Molecular Structure</topic><topic>oak barrels</topic><topic>oxidation</topic><topic>polyphenols</topic><topic>Quercus robur</topic><topic>release</topic><topic>solubility</topic><topic>Solutions</topic><topic>spectral analysis</topic><topic>tannins</topic><topic>Tannins - chemistry</topic><topic>Tannins - isolation & purification</topic><topic>Wood</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Puech, Jean-Louis</creatorcontrib><creatorcontrib>Mertz, Christian</creatorcontrib><creatorcontrib>Michon, Véronique</creatorcontrib><creatorcontrib>Le Guernevé, Christine</creatorcontrib><creatorcontrib>Doco, Thierry</creatorcontrib><creatorcontrib>Hervé du Penhoat, Catherine</creatorcontrib><collection>AGRIS</collection><collection>Istex</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>Puech, Jean-Louis</au><au>Mertz, Christian</au><au>Michon, Véronique</au><au>Le Guernevé, Christine</au><au>Doco, Thierry</au><au>Hervé du Penhoat, Catherine</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Evolution of Castalagin and Vescalagin in Ethanol Solutions. Identification of New Derivatives</atitle><jtitle>Journal of agricultural and food chemistry</jtitle><addtitle>J. Agric. Food Chem</addtitle><date>1999-05-01</date><risdate>1999</risdate><volume>47</volume><issue>5</issue><spage>2060</spage><epage>2066</epage><pages>2060-2066</pages><issn>0021-8561</issn><eissn>1520-5118</eissn><coden>JAFCAU</coden><abstract>Brandies, cognac, armagnac, whiskeys, and rums are aged in oak barrels to improve their organoleptic properties. During this period, numerous compounds such as ellagitannins are extracted from the wood and can subsequently be transformed into new derivatives by chemical reactions. Model solutions of castalagin and vescalagin have been studied to determine the behavior of polyphenols in ethanol−water. Upon prolonged exposure to 40 and 70% (v/v) ethanol at room temperature, hemiketal derivatives containing ethoxy groups have been characterized by LC/MS and NMR. These compounds further evolve to afford the corresponding ketals. 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| identifier | ISSN: 0021-8561 |
| ispartof | Journal of agricultural and food chemistry, 1999-05, Vol.47 (5), p.2060-2066 |
| issn | 0021-8561 1520-5118 |
| language | eng |
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| source | MEDLINE; ACS Publications |
| subjects | Alcoholic Beverages Antihypertensive Agents - chemistry Biological and medical sciences Biphenyl Compounds Brandies, spirituous liquors Catechols - chemistry chemical reactions chemical structure Chromatography, High Pressure Liquid containers derivatives elagitannins Ethanol ethoxylation Fermented food industries Food Handling Food industries Fundamental and applied biological sciences. Psychology Hydrolyzable Tannins Molecular Conformation Molecular Structure oak barrels oxidation polyphenols Quercus robur release solubility Solutions spectral analysis tannins Tannins - chemistry Tannins - isolation & purification Wood |
| title | Evolution of Castalagin and Vescalagin in Ethanol Solutions. Identification of New Derivatives |
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