The oxidation mechanism of the antioxidant quercetin in nonaqueous media (Articolo in rivista)

Type
Label
  • The oxidation mechanism of the antioxidant quercetin in nonaqueous media (Articolo in rivista) (literal)
Anno
  • 2011-01-01T00:00:00+01:00 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi
  • 10.1016/j.electacta.2011.04.121 (literal)
Alternative label
  • Sokolová, Romana; Degano, Ilaria; Ramesova, Sárka; Bulícková, Jana; Hromadová, Magdaléna; Gál, Miroslav; Fiedler, Jan; Valásek, Michal (2011)
    The oxidation mechanism of the antioxidant quercetin in nonaqueous media
    in Electrochimica acta
    (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
  • Sokolová, Romana; Degano, Ilaria; Ramesova, Sárka; Bulícková, Jana; Hromadová, Magdaléna; Gál, Miroslav; Fiedler, Jan; Valásek, Michal (literal)
Pagina inizio
  • 7421 (literal)
Pagina fine
  • 7427 (literal)
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  • 56 (literal)
Rivista
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  • 6 (literal)
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  • 21 (literal)
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  • J. Heyrovský Institute of Physical Chemistry of the Academy of Sciences of the Czech Republic, v.v.i. Dolejskova 3, 18223 Prague, Czech Republic; Department of Chemistry and Industrial Chemistry, University of Pisa, Via Risorgimento 35, 56100 Pisa, Italy; Institute of Organic Chemistry and Biochemistry of the Academy of Sciences of the Czech Republic, v.v.i. Flemingovo nám. 2, 16610 Prague, Czech Republic; (literal)
Titolo
  • The oxidation mechanism of the antioxidant quercetin in nonaqueous media (literal)
Abstract
  • The knowledge of the degradation pathways of natural dyes used in medieval textiles is necessary for the restoration of their original color. Quercetin, one of such colorants, reportedly yields the wide spectrum of oxidation products in different types of media. This study deals with electrochemical oxidation mechanism of quercetin in nonaqueous solution, which has not been yet attempted. The final oxidation product at the first oxidation wave was identified by HPLC-DAD and GC-MS techniques as 2-(3?,4?-dihydroxybenzoyl)-2,4,6-trihydroxybenzofuran-3(2H)-one. The apparent two-electron process at the potential of the first oxidation wave yields current-voltage shapes with one-electron characteristics. The in situ spectroelectrochemistry measurements proved the oxidation mechanism leading through a short-lived anion radical. Two possibilities of the oxidation mechanism are discussed: two one-electron transfers, which do not have identical but similar redox potentials, or the presence of a disproportionation chemical reaction following the first one electron transfer. The quinone formed in either case is stable only on the time scale of a fast spectroelectrochemistry and undergoes fast hydroxylation reaction, where 2-(3,4-dihydroxybenzoyl)-2,4,6-trihydroxybenzofuran-3-one is formed. This compound is oxidized at the potential of the second oxidation wave of quercetin. (literal)
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