Color stability and spectroscopic properties of deoxyvitisins in aqueous solution

Andre Sousa, Luis Cabrita, Paula Araujo, Nuno Mateus, Fernando Pina, Victor de Freitas

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

The color properties and stability of three types of 3-deoxyvitisins derived from peonidin (deoxyvitisin A, B and methyldeoxyvitisin) were studied using UV-Visible spectroscopy. Similarly to pyranoanthocyanins, the conjugated double bonds among pyranic rings C and D provide a higher electronic delocalization that prevents the nucleophilic attack of water at position 2 and the subsequent formation of the hemiketal and chalcone species. Consequently, besides the flavylium cation (AH(+)), neutral (A) and ionized bases (A(n-)) have been identified by increasing pH, and the respective acidity constants were determined. The acidity constant values for the formation of the neutral quinoidal base (pK(a2(deoxyvit A)) = 4.8, pK(a1(deoxyvit B)) = 4.7 and pK(a1(methyldeoxyvitisin)) = 5.2) are slightly higher than the ones reported in the literature for their corresponding 3-glucosyl derivatives (vitisins). Given their higher stability, these pigments may be regarded as potential food colorants.

Original languageEnglish
Pages (from-to)539-544
Number of pages6
JournalNew Journal of Chemistry
Volume38
Issue number2
DOIs
Publication statusPublished - Feb 2014

Keywords

  • ANTHOCYANIN-DERIVED PIGMENTS
  • RED WINES
  • EQUILIBRIUM FORMS
  • FLAVYLIUM SALTS
  • VITISIN-B
  • DEOXYANTHOCYANIDINS
  • ACID
  • DYE

Cite this