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Color stability and spectroscopic properties of deoxyvitisins in aqueous solution†
André Sousa,Luís Cabrita,Paula Araújo,Nuno Mateus,Fernando Pina,Victor de Freitas
New Journal of Chemistry Pub Date : 11/12/2013 00:00:00 , DOI:10.1039/C3NJ01271A
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 (An) 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 (pKa2(deoxyvit A) = 4.8, pKa1(deoxyvit B) = 4.7 and pKa1(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.

Graphical abstract: Color stability and spectroscopic properties of deoxyvitisins in aqueous solution
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