Coupling reactions between flavylium ions and catechin

[EN] In order to model natural polymeric pigments present in old red wines, new covalent adducts have been synthesized upon condensation of synthetic flavylium ions (models of anthocyanins) with catechin (model of tannins) in the presence and in the absence of acetaldehyde. These new pigments have b...

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Detalles Bibliográficos
Autores: Escribano Bailón, María Teresa, Dangles, Olivier, Brouillard, Raymond
Tipo de recurso: artículo
Fecha de publicación:1996
País:España
Institución:Universidad de Salamanca (USAL)
Repositorio:GREDOS. Repositorio Institucional de la Universidad de Salamanca
OAI Identifier:oai:gredos.usal.es:10366/139436
Acceso en línea:http://hdl.handle.net/10366/139436
Access Level:acceso abierto
Palabra clave:Flavylium ions
Biochemistry
Anthocyanins
Tannins
Catechin
Acetaldehyde
Copigmentation
Self-association
Red wine pigments
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spelling Coupling reactions between flavylium ions and catechinEscribano Bailón, María TeresaDangles, OlivierBrouillard, RaymondFlavylium ionsBiochemistryAnthocyaninsTanninsCatechinAcetaldehydeCopigmentationSelf-associationRed wine pigments[EN] In order to model natural polymeric pigments present in old red wines, new covalent adducts have been synthesized upon condensation of synthetic flavylium ions (models of anthocyanins) with catechin (model of tannins) in the presence and in the absence of acetaldehyde. These new pigments have been investigated by 1D and 2D NMR, HPLC, FAB-mass and UV-visible spectroscopies and molecular modelling. The two flavylium salts used in this work (3,4'-dimethoxy-7-hydroxyflavylium chloride and 5,7-dihydroxy-3,4'-dimethoxyflavylium chloride) display quite different reactivities toward catechin. The electronic donating effect of the catechin moiety and the formation of noncovalent dimers in acidic aqueous or methanolic solution should be mainly responsible for the improved stability of the flavylium chromophore in the new pigments.201920191996info:eu-repo/semantics/articlehttp://hdl.handle.net/10366/139436reponame:GREDOS. Repositorio Institucional de la Universidad de Salamancainstname:Universidad de Salamanca (USAL)InglésAttribution-NonCommercial-NoDerivs 3.0 Unportedhttps://creativecommons.org/licenses/by-nc-nd/3.0/info:eu-repo/semantics/openAccessoai:gredos.usal.es:10366/1394362026-06-07T06:28:51Z
dc.title.none.fl_str_mv Coupling reactions between flavylium ions and catechin
title Coupling reactions between flavylium ions and catechin
spellingShingle Coupling reactions between flavylium ions and catechin
Escribano Bailón, María Teresa
Flavylium ions
Biochemistry
Anthocyanins
Tannins
Catechin
Acetaldehyde
Copigmentation
Self-association
Red wine pigments
title_short Coupling reactions between flavylium ions and catechin
title_full Coupling reactions between flavylium ions and catechin
title_fullStr Coupling reactions between flavylium ions and catechin
title_full_unstemmed Coupling reactions between flavylium ions and catechin
title_sort Coupling reactions between flavylium ions and catechin
dc.creator.none.fl_str_mv Escribano Bailón, María Teresa
Dangles, Olivier
Brouillard, Raymond
author Escribano Bailón, María Teresa
author_facet Escribano Bailón, María Teresa
Dangles, Olivier
Brouillard, Raymond
author_role author
author2 Dangles, Olivier
Brouillard, Raymond
author2_role author
author
dc.subject.none.fl_str_mv Flavylium ions
Biochemistry
Anthocyanins
Tannins
Catechin
Acetaldehyde
Copigmentation
Self-association
Red wine pigments
topic Flavylium ions
Biochemistry
Anthocyanins
Tannins
Catechin
Acetaldehyde
Copigmentation
Self-association
Red wine pigments
description [EN] In order to model natural polymeric pigments present in old red wines, new covalent adducts have been synthesized upon condensation of synthetic flavylium ions (models of anthocyanins) with catechin (model of tannins) in the presence and in the absence of acetaldehyde. These new pigments have been investigated by 1D and 2D NMR, HPLC, FAB-mass and UV-visible spectroscopies and molecular modelling. The two flavylium salts used in this work (3,4'-dimethoxy-7-hydroxyflavylium chloride and 5,7-dihydroxy-3,4'-dimethoxyflavylium chloride) display quite different reactivities toward catechin. The electronic donating effect of the catechin moiety and the formation of noncovalent dimers in acidic aqueous or methanolic solution should be mainly responsible for the improved stability of the flavylium chromophore in the new pigments.
publishDate 1996
dc.date.none.fl_str_mv 1996
2019
2019
dc.type.none.fl_str_mv info:eu-repo/semantics/article
format article
dc.identifier.none.fl_str_mv http://hdl.handle.net/10366/139436
url http://hdl.handle.net/10366/139436
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.rights.none.fl_str_mv Attribution-NonCommercial-NoDerivs 3.0 Unported
https://creativecommons.org/licenses/by-nc-nd/3.0/
info:eu-repo/semantics/openAccess
rights_invalid_str_mv Attribution-NonCommercial-NoDerivs 3.0 Unported
https://creativecommons.org/licenses/by-nc-nd/3.0/
eu_rights_str_mv openAccess
dc.source.none.fl_str_mv reponame:GREDOS. Repositorio Institucional de la Universidad de Salamanca
instname:Universidad de Salamanca (USAL)
instname_str Universidad de Salamanca (USAL)
reponame_str GREDOS. Repositorio Institucional de la Universidad de Salamanca
collection GREDOS. Repositorio Institucional de la Universidad de Salamanca
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15.301603

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