Model Studies on the Effect of Aldehyde Structure on Their Selective Trapping by Phenolic Compounds

6 Figuras; 3 Tablas; 33 Páginas

Detalles Bibliográficos
Autores: Hidalgo, Francisco J., Aguilar Tellez, Isabel, Zamora, Rosario
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2017
País:España
Institución:Consejo Superior de Investigaciones Científicas (CSIC)
Repositorio:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/156167
Acceso en línea:http://hdl.handle.net/10261/156167
Access Level:acceso abierto
Palabra clave:Aldehydes
Carbonyl–phenol reactions
Lipid oxidation
Maillard reaction
Phenols
Reactive carbonyls
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spelling Model Studies on the Effect of Aldehyde Structure on Their Selective Trapping by Phenolic CompoundsHidalgo, Francisco J.Aguilar Tellez, IsabelZamora, RosarioAldehydesCarbonyl–phenol reactionsLipid oxidationMaillard reactionPhenolsReactive carbonyls6 Figuras; 3 Tablas; 33 PáginasThe reaction among flavor-relevant saturated aldehydes (propanal, 2-methylpropanal, butanal, 2-methylbutanal, 3-methylbutanal, pentanal, hexanal, and glyoxal) and phenolic compounds (resorcinol, 2-methylresorcinol, 2,5-dimethylresorcinol, and orcinol) was studied both to identify and to characterize the formed carbonyl–phenol adducts and to understand the differences in the carbonyl-trapping abilities of phenolic compounds. The obtained results showed that carbonyl-trapping by phenolics is selective and that the formation of carbonyl–phenol adducts depends on the structures of both the phenol and aldehyde involved. In relation to the phenolic derivative, the presence of groups that increase the nucleophilicity of phenolic carbons will increase the carbonyl-trapping ability of these compounds. On the other hand, the presence of groups that increase the steric hindrance of these positions without affecting nucleophilicity will inhibit the reaction. Analogously, the presence of branching at position 2 of the aldehyde will also inhibit the reaction by steric hindrance. All of these results suggest that the addition of phenolics to foods may change food flavor not only because of their sensory properties but also because they can modify the ratio among food odorants by selective reaction of phenolics with determined carbonyl compounds.This study was supported in part by the European Union (FEDER funds) and the Plan Nacional de I + D of the Ministerio de Economı́a y Competitividad of Spain (Project AGL2015-68186-R).Peer reviewedAmerican Chemical SocietyMinisterio de Economía y Competitividad (España)Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]201720172017info:eu-repo/semantics/articlehttp://purl.org/coar/resource_type/c_6501Postprintinfo:eu-repo/semantics/acceptedVersionhttp://hdl.handle.net/10261/156167reponame:DIGITAL.CSIC. Repositorio Institucional del CSICinstname:Consejo Superior de Investigaciones Científicas (CSIC)Inglés#PLACEHOLDER_PARENT_METADATA_VALUE#info:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/AGL2015-68186-Rhttp://dx.doi.org/10.1021/acs.jafc.7b01081Síinfo:eu-repo/semantics/openAccessoai:digital.csic.es:10261/1561672026-05-22T06:33:51Z
dc.title.none.fl_str_mv Model Studies on the Effect of Aldehyde Structure on Their Selective Trapping by Phenolic Compounds
title Model Studies on the Effect of Aldehyde Structure on Their Selective Trapping by Phenolic Compounds
spellingShingle Model Studies on the Effect of Aldehyde Structure on Their Selective Trapping by Phenolic Compounds
Hidalgo, Francisco J.
Aldehydes
Carbonyl–phenol reactions
Lipid oxidation
Maillard reaction
Phenols
Reactive carbonyls
title_short Model Studies on the Effect of Aldehyde Structure on Their Selective Trapping by Phenolic Compounds
title_full Model Studies on the Effect of Aldehyde Structure on Their Selective Trapping by Phenolic Compounds
title_fullStr Model Studies on the Effect of Aldehyde Structure on Their Selective Trapping by Phenolic Compounds
title_full_unstemmed Model Studies on the Effect of Aldehyde Structure on Their Selective Trapping by Phenolic Compounds
title_sort Model Studies on the Effect of Aldehyde Structure on Their Selective Trapping by Phenolic Compounds
dc.creator.none.fl_str_mv Hidalgo, Francisco J.
Aguilar Tellez, Isabel
Zamora, Rosario
author Hidalgo, Francisco J.
author_facet Hidalgo, Francisco J.
Aguilar Tellez, Isabel
Zamora, Rosario
author_role author
author2 Aguilar Tellez, Isabel
Zamora, Rosario
author2_role author
author
dc.contributor.none.fl_str_mv Ministerio de Economía y Competitividad (España)
Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]
dc.subject.none.fl_str_mv Aldehydes
Carbonyl–phenol reactions
Lipid oxidation
Maillard reaction
Phenols
Reactive carbonyls
topic Aldehydes
Carbonyl–phenol reactions
Lipid oxidation
Maillard reaction
Phenols
Reactive carbonyls
description 6 Figuras; 3 Tablas; 33 Páginas
publishDate 2017
dc.date.none.fl_str_mv 2017
2017
2017
dc.type.none.fl_str_mv info:eu-repo/semantics/article
http://purl.org/coar/resource_type/c_6501
Postprint
info:eu-repo/semantics/acceptedVersion
format article
status_str acceptedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/10261/156167
url http://hdl.handle.net/10261/156167
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv #PLACEHOLDER_PARENT_METADATA_VALUE#
info:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/AGL2015-68186-R
http://dx.doi.org/10.1021/acs.jafc.7b01081
Sí
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.publisher.none.fl_str_mv American Chemical Society
publisher.none.fl_str_mv American Chemical Society
dc.source.none.fl_str_mv reponame:DIGITAL.CSIC. Repositorio Institucional del CSIC
instname:Consejo Superior de Investigaciones Científicas (CSIC)
instname_str Consejo Superior de Investigaciones Científicas (CSIC)
reponame_str DIGITAL.CSIC. Repositorio Institucional del CSIC
collection DIGITAL.CSIC. Repositorio Institucional del CSIC
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15,811543

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