Structural transformations of the synthetic salt 4', 7-dihydroxyflavylium chloride in acid and basic aqueous solutions. Part 1 - Ground state

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Abstract

A complete study of the structural pH dependent transformations of the synthetic flavylium salt 4',7-dihydroxyflavylium chloride (DHF). occurring in aqueous solutions, including the basic region, is described. The kinetic study of the transformations occuring in acidic media (quinoidal base (A) ⇄ flavylium cation (AFT) ⇄ hemiacetal (B) ⇄ cis-chalcone (Ctrans) ⇄ trans-chalcone (Ctrans)) allowed to conclude that the cis-trans isomerization is faster than the tautomerization and the hydration processes, which is unique in the anthocyanins family. Results obtained with the parent compound 4",7dimethoxyflavylium chloride (DMF) with relevance to this study are also presented. In equilibrated basic solutions the existence of acid-base equilibria involving the trans-Chalcone (Ctrans) and its conjugated bases. (C transand C2trans), was detected. Freshly prepared solutions at pH >7 show also the presence of a transient species identified as the ionized quinoidal base (A-), which is almost completely converted into C2-trans with a pH dependent rate constant.

Original languageEnglish
Pages (from-to)111-118
Number of pages8
JournalAnales De Quimica
Volume93
Issue number2
Publication statusPublished - 1 Dec 1997

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Chalcone
Ground state
Chlorides
Salts
Acids
Anthocyanins
Isomerization
Hydration
Cations
Rate constants
Kinetics
4',7-dihydroxyflavylium

Keywords

  • Anthocyanins
  • Equilibria
  • Kinetics
  • NMR
  • UV-Vis absorption

Cite this

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title = "Structural transformations of the synthetic salt 4', 7-dihydroxyflavylium chloride in acid and basic aqueous solutions. Part 1 - Ground state",
abstract = "A complete study of the structural pH dependent transformations of the synthetic flavylium salt 4',7-dihydroxyflavylium chloride (DHF). occurring in aqueous solutions, including the basic region, is described. The kinetic study of the transformations occuring in acidic media (quinoidal base (A) ⇄ flavylium cation (AFT) ⇄ hemiacetal (B) ⇄ cis-chalcone (Ctrans) ⇄ trans-chalcone (Ctrans)) allowed to conclude that the cis-trans isomerization is faster than the tautomerization and the hydration processes, which is unique in the anthocyanins family. Results obtained with the parent compound 4{"},7dimethoxyflavylium chloride (DMF) with relevance to this study are also presented. In equilibrated basic solutions the existence of acid-base equilibria involving the trans-Chalcone (Ctrans) and its conjugated bases. (C transand C2trans), was detected. Freshly prepared solutions at pH >7 show also the presence of a transient species identified as the ionized quinoidal base (A-), which is almost completely converted into C2-trans with a pH dependent rate constant.",
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author = "Fernando Pina and Lina Benedito and M{\'e}lo, {Maria Jo{\~a}o} and Parola, {A. J.} and Lima, {Jo{\~a}o C.} and Ma{\cc}anita, {Ant{\'o}nio L.}",
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T1 - Structural transformations of the synthetic salt 4', 7-dihydroxyflavylium chloride in acid and basic aqueous solutions. Part 1 - Ground state

AU - Pina, Fernando

AU - Benedito, Lina

AU - Mélo, Maria João

AU - Parola, A. J.

AU - Lima, João C.

AU - Maçanita, António L.

PY - 1997/12/1

Y1 - 1997/12/1

N2 - A complete study of the structural pH dependent transformations of the synthetic flavylium salt 4',7-dihydroxyflavylium chloride (DHF). occurring in aqueous solutions, including the basic region, is described. The kinetic study of the transformations occuring in acidic media (quinoidal base (A) ⇄ flavylium cation (AFT) ⇄ hemiacetal (B) ⇄ cis-chalcone (Ctrans) ⇄ trans-chalcone (Ctrans)) allowed to conclude that the cis-trans isomerization is faster than the tautomerization and the hydration processes, which is unique in the anthocyanins family. Results obtained with the parent compound 4",7dimethoxyflavylium chloride (DMF) with relevance to this study are also presented. In equilibrated basic solutions the existence of acid-base equilibria involving the trans-Chalcone (Ctrans) and its conjugated bases. (C transand C2trans), was detected. Freshly prepared solutions at pH >7 show also the presence of a transient species identified as the ionized quinoidal base (A-), which is almost completely converted into C2-trans with a pH dependent rate constant.

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