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A New Insight into the Degradation of Anthocyanins: Reversible versus the Irreversible Chemical Processes

2022-01-19Artigo científico Acesso aberto
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dc.contributor.authorSousa, Diogo
dc.contributor.authorBasílio, Nuno
dc.contributor.authorOliveira, Joana
dc.contributor.authorde Freitas, Victor
dc.contributor.authorPina, Fernando
dc.contributor.institutionDQ - Departamento de Química
dc.contributor.pblACS - American Chemical Society
dc.date.accessioned2022-06-29T22:29:43Z
dc.date.available2023-01-05T01:32:38Z
dc.date.embargoedUntil2023-01-04
dc.date.issued2022-01-19
dc.descriptionPublisher Copyright: © 2022 American Chemical Society
dc.description.abstractThe kinetics and thermodynamics of the pH-dependent reversible and irreversible processes leading to color fading of pelargonidin-3-O-glucoside, peonidin-3-O-glucoside, malvidin-3-O-glucoside, and cyanidin-3-O-glucoside dyes in aqueous solutions are reported. Following the addition of base to the flavylium cation, the quinoidal bases disappear by three distinct steps: (i) in an acidic medium by a biexponential process, in which the faster step is controlled by the hydration reaction and the slower one by cis–trans isomerization; the degradation process occurs essentially from the anionic quinoidal base; (ii) in a basic medium (pH > 9.5), in which the disappearance of the anionic bases is monoexponential, with the rate proportional to the hydroxyl concentration (hydroxyl attack), leading to anionic chalcones (cis and trans) at equilibrium─the slower degradation step occurs from the di- and trianionic chalcones; and (iii) in the pH region circa 7.7 < pH < 9.5, in which hydration and hydroxyl attacks are much slower than anionic quinoidal base degradation (which is the rate-controlling step) and the equilibrium cannot be attained.en
dc.description.versionauthorsversion
dc.description.versionpublished
dc.format.extent13
dc.format.extent4754885
dc.identifier.doi10.1021/acs.jafc.1c06521
dc.identifier.issn0021-8561
dc.identifier.otherPURE: 42244518
dc.identifier.otherPURE UUID: 7a6bf19d-5f74-4b74-ab86-c01a59f2d9a2
dc.identifier.otherScopus: 85122756786
dc.identifier.otherPubMed: 34982560
dc.identifier.otherWOS: 000740952200001
dc.identifier.otherORCID: /0000-0001-8529-6848/work/109596376
dc.identifier.urihttp://hdl.handle.net/10362/141060
dc.identifier.urlhttps://www.scopus.com/pages/publications/85122756786
dc.language.isoeng
dc.peerreviewedyes
dc.relationFunding Information: info:eu-repo/grantAgreement/FCT/Investigador FCT/IF%2F00225%2F2015%2FCP1279%2FCT0001/PT
dc.relationinfo:eu-repo/grantAgreement/FCT/CEEC IND 2017/CEECIND%2F00466%2F2017%2FCP1462%2FCT0013/PT
dc.relationNot Available
dc.relationCarbon dots from industrial biomass wastes: synthesis, luminescence and chiral properties
dc.subjectanthocyanins
dc.subjectdegradation kinetics
dc.subjectdirect and reverse pH jumps
dc.subjectstopped flow
dc.subjectGeneral Chemistry
dc.subjectGeneral Agricultural and Biological Sciences
dc.titleA New Insight into the Degradation of Anthocyanins: Reversible versus the Irreversible Chemical Processesen
dc.typejournal article
degois.publication.firstPage656
degois.publication.issue2
degois.publication.lastPage668
degois.publication.titleJournal of Agricultural and Food Chemistry
degois.publication.volume70
dspace.entity.typePublication
oaire.awardNumberCEECIND/00466/2017/CP1462/CT0013
oaire.awardNumberSFRH/BD/143369/2019
oaire.awardTitleNot Available
oaire.awardTitleCarbon dots from industrial biomass wastes: synthesis, luminescence and chiral properties
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/CEEC IND 2017/CEECIND%2F00466%2F2017%2FCP1462%2FCT0013/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/OE/SFRH%2FBD%2F143369%2F2019/PT
oaire.fundingStreamCEEC IND 2017
oaire.fundingStreamOE
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.nameFundação para a Ciência e a Tecnologia
project.funder.nameFundação para a Ciência e a Tecnologia
rcaap.rightsopenAccess
relation.isProjectOfPublication2f49aaab-813e-4034-9d8d-67553a970bd6
relation.isProjectOfPublicationd2f6878f-f564-4726-9e66-ad546b188e7b
relation.isProjectOfPublication.latestForDiscovery2f49aaab-813e-4034-9d8d-67553a970bd6

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