PH-Dependent Multistate System Generated by a Synthetic Furanoflavylium Compound: An Ancestor of the Anthocyanin Multistate of Chemical Species

Detalhes bibliográficos
Autor(a) principal: Alejo-Armijo, A.
Data de Publicação: 2019
Outros Autores: Parola, A. Jorge, Pina, Fernando
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositórios Científicos de Acesso Aberto de Portugal (RCAAP)
Texto Completo: https://doi.org/10.1021/acsomega.8b03696
Resumo: This work was supported by the Associate Laboratory for Green Chemistry-LAQV, which is financed by national funds from FCT/MCTES (UID/QUI/50006/2019). FCT/MCTES is also acknowledged through the National Portuguese NMR Network RECI/BBB-BQB/0230/2012. A.A.-A. is grateful for the postdoctoral fellowship from Fundacion Alfonso Marti0n Escudero.
id RCAP_ddd0f4922148ccb597dc3eac4dec403e
oai_identifier_str oai:run.unl.pt:10362/75563
network_acronym_str RCAP
network_name_str Repositórios Científicos de Acesso Aberto de Portugal (RCAAP)
repository_id_str https://opendoar.ac.uk/repository/7160
spelling PH-Dependent Multistate System Generated by a Synthetic Furanoflavylium Compound: An Ancestor of the Anthocyanin Multistate of Chemical SpeciesChemistry(all)Chemical Engineering(all)This work was supported by the Associate Laboratory for Green Chemistry-LAQV, which is financed by national funds from FCT/MCTES (UID/QUI/50006/2019). FCT/MCTES is also acknowledged through the National Portuguese NMR Network RECI/BBB-BQB/0230/2012. A.A.-A. is grateful for the postdoctoral fellowship from Fundacion Alfonso Marti0n Escudero.The multistate of chemical species generated by 4′-hydroxy-3,2′-furanoflavylium is similar to that of anthocyanins and related compounds. This furanoflavylium multistate system was fully characterized by UV-visible and NMR spectroscopy, allowing determination of the respective equilibrium and rate constants. In contrast to the multistate generated by flavylium cations derived from anthocyanins and related compounds, the furanoflavylium multistate is characterized by much slower hydration and tautomerization (pyran ring opening-closing). In addition, the cis-trans isomerization of the chalcones of this system (2′-hydroxyaurones) is extremely slow when compared with anthocyanins. The observed similar order of magnitude for tautomerization and isomerization rate constants leads to peculiar kinetics from the flavylium cation (pH = 1) to the stable trans-chalcone (higher pH values). The hemiketal appears and disappears during the first stages of the kinetics, which gives the intermediate cis-chalcone (pseudo-equilibrium). This last species disappears in a much slower process, as fully characterized by 1 H NMR, to give the final trans-chalcone.LAQV@REQUIMTEDQ - Departamento de QuímicaRUNAlejo-Armijo, A.Parola, A. JorgePina, Fernando2019-07-15T22:39:59Z2019-02-222019-02-22T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/article10application/pdfhttps://doi.org/10.1021/acsomega.8b03696eng2470-1343PURE: 12855979http://www.scopus.com/inward/record.url?scp=85062442916&partnerID=8YFLogxKhttps://doi.org/10.1021/acsomega.8b03696info:eu-repo/semantics/openAccessreponame:Repositórios Científicos de Acesso Aberto de Portugal (RCAAP)instname:FCCN, serviços digitais da FCT – Fundação para a Ciência e a Tecnologiainstacron:RCAAP2024-05-22T17:40:17Zoai:run.unl.pt:10362/75563Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireinfo@rcaap.ptopendoar:https://opendoar.ac.uk/repository/71602025-05-28T17:11:19.541216Repositórios Científicos de Acesso Aberto de Portugal (RCAAP) - FCCN, serviços digitais da FCT – Fundação para a Ciência e a Tecnologiafalse
dc.title.none.fl_str_mv PH-Dependent Multistate System Generated by a Synthetic Furanoflavylium Compound: An Ancestor of the Anthocyanin Multistate of Chemical Species
title PH-Dependent Multistate System Generated by a Synthetic Furanoflavylium Compound: An Ancestor of the Anthocyanin Multistate of Chemical Species
spellingShingle PH-Dependent Multistate System Generated by a Synthetic Furanoflavylium Compound: An Ancestor of the Anthocyanin Multistate of Chemical Species
Alejo-Armijo, A.
Chemistry(all)
Chemical Engineering(all)
title_short PH-Dependent Multistate System Generated by a Synthetic Furanoflavylium Compound: An Ancestor of the Anthocyanin Multistate of Chemical Species
title_full PH-Dependent Multistate System Generated by a Synthetic Furanoflavylium Compound: An Ancestor of the Anthocyanin Multistate of Chemical Species
title_fullStr PH-Dependent Multistate System Generated by a Synthetic Furanoflavylium Compound: An Ancestor of the Anthocyanin Multistate of Chemical Species
title_full_unstemmed PH-Dependent Multistate System Generated by a Synthetic Furanoflavylium Compound: An Ancestor of the Anthocyanin Multistate of Chemical Species
title_sort PH-Dependent Multistate System Generated by a Synthetic Furanoflavylium Compound: An Ancestor of the Anthocyanin Multistate of Chemical Species
author Alejo-Armijo, A.
author_facet Alejo-Armijo, A.
Parola, A. Jorge
Pina, Fernando
author_role author
author2 Parola, A. Jorge
Pina, Fernando
author2_role author
author
dc.contributor.none.fl_str_mv LAQV@REQUIMTE
DQ - Departamento de Química
RUN
dc.contributor.author.fl_str_mv Alejo-Armijo, A.
Parola, A. Jorge
Pina, Fernando
dc.subject.por.fl_str_mv Chemistry(all)
Chemical Engineering(all)
topic Chemistry(all)
Chemical Engineering(all)
description This work was supported by the Associate Laboratory for Green Chemistry-LAQV, which is financed by national funds from FCT/MCTES (UID/QUI/50006/2019). FCT/MCTES is also acknowledged through the National Portuguese NMR Network RECI/BBB-BQB/0230/2012. A.A.-A. is grateful for the postdoctoral fellowship from Fundacion Alfonso Marti0n Escudero.
publishDate 2019
dc.date.none.fl_str_mv 2019-07-15T22:39:59Z
2019-02-22
2019-02-22T00:00:00Z
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
format article
status_str publishedVersion
dc.identifier.uri.fl_str_mv https://doi.org/10.1021/acsomega.8b03696
url https://doi.org/10.1021/acsomega.8b03696
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 2470-1343
PURE: 12855979
http://www.scopus.com/inward/record.url?scp=85062442916&partnerID=8YFLogxK
https://doi.org/10.1021/acsomega.8b03696
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv 10
application/pdf
dc.source.none.fl_str_mv reponame:Repositórios Científicos de Acesso Aberto de Portugal (RCAAP)
instname:FCCN, serviços digitais da FCT – Fundação para a Ciência e a Tecnologia
instacron:RCAAP
instname_str FCCN, serviços digitais da FCT – Fundação para a Ciência e a Tecnologia
instacron_str RCAAP
institution RCAAP
reponame_str Repositórios Científicos de Acesso Aberto de Portugal (RCAAP)
collection Repositórios Científicos de Acesso Aberto de Portugal (RCAAP)
repository.name.fl_str_mv Repositórios Científicos de Acesso Aberto de Portugal (RCAAP) - FCCN, serviços digitais da FCT – Fundação para a Ciência e a Tecnologia
repository.mail.fl_str_mv info@rcaap.pt
_version_ 1833596503117004800

Registros relacionados