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Phenolic acids and derivatives: studies on the relationship among structure, radical scavenging activity, and physicochemical parameters

2000Journal article Open access
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dc.contributor.authorSilva, Francisco A. M.
dc.contributor.authorBorges, Fernanda
dc.contributor.authorGuimarães, Carla
dc.contributor.authorLima, José L. F. C.
dc.contributor.authorMatos, Carla
dc.contributor.authorReis, Salette
dc.date.accessioned2019-12-24T09:53:34Z
dc.date.available2019-12-24T09:53:34Z
dc.date.issued2000
dc.description.abstractThe antiradical activity of caffeic acid (1), dihydrocaffeic acid (5), and their corresponding n-alkyl esters was evaluated by using the 2,2-diphenyl-1-picrylhydrazyl radical (DPPH(*)) method. Dihydrocaffeic acid (5) was the most potent compound, having an antiradical effect higher than that of (+/-)-alpha-tocopherol, whereas caffeic acid (1) was less efficient. Esterification of the carboxyl group of dihydrocaffeic acid (5) had a dramatic effect on its antiradical potency, but similar effects were not observed for caffeic acid (1) derivatives. The n-alkyl esters of both phenolic series had similar potencies, and their antiradical activities were independent of the alkyl chain length. Dose-dependent scavenger effects were found in both series. Acid-base properties of the compounds, evaluated by using potentiometry and spectrophotometry, showed that the catechol moiety had pK(a2) and pK(a3) values of 9. 24-9.02 and 11.38-10.99 in the dihydrocaffeic series and 8.48-8.24 and 11.38-11.07 in the caffeic series, respectively. Antiradical activity and pK(a) values of the compounds were not related.pt_PT
dc.description.versioninfo:eu-repo/semantics/publishedVersionpt_PT
dc.identifier.doi10.1021/jf9913110pt_PT
dc.identifier.issn0021-8561
dc.identifier.urihttp://hdl.handle.net/10284/8322
dc.language.isoengpt_PT
dc.peerreviewedyespt_PT
dc.subjectAntioxidantspt_PT
dc.subjectCaffeic acidspt_PT
dc.subjectEsterspt_PT
dc.subjectFree radical scavengerspt_PT
dc.subjectFree radicalspt_PT
dc.subjectPhenolspt_PT
dc.subjectPotentiometrypt_PT
dc.subjectStructure-activity relationshippt_PT
dc.subjectVitamin Ept_PT
dc.titlePhenolic acids and derivatives: studies on the relationship among structure, radical scavenging activity, and physicochemical parameterspt_PT
dc.typejournal article
dspace.entity.typePublication
oaire.citation.endPage2126pt_PT
oaire.citation.issue6pt_PT
oaire.citation.startPage2122pt_PT
oaire.citation.titleJournal of Agricultural and Food Chemistrypt_PT
oaire.citation.volume48pt_PT
person.familyNameMoutinho
person.familyNameMatos
person.givenNameCarla
person.givenNameCarla
person.identifier1536969
person.identifier.ciencia-idB61F-F356-80C6
person.identifier.ciencia-id721C-DA34-256E
person.identifier.orcid0000-0003-1310-4696
person.identifier.orcid0000-0003-0617-3538
person.identifier.ridM-7142-2013
person.identifier.scopus-author-id16064733800
person.identifier.scopus-author-id7004493818
rcaap.rightsopenAccesspt_PT
rcaap.typearticlept_PT
relation.isAuthorOfPublicationcff7638e-1f33-4384-aa73-d3acc5cca5f8
relation.isAuthorOfPublicationd4b6d3e1-6d29-4fb4-97c7-abb2cf4c83b4
relation.isAuthorOfPublication.latestForDiscoverycff7638e-1f33-4384-aa73-d3acc5cca5f8

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