Synthesis of a new bluish pigment from the reaction of a methylpyranoanthocyanin with sinapaldehyde

Abstract

The synthesis of a new pigment with a bluish color was obtained from the reaction of methylpyranomalvidin-3-glucoside with sinapaldehyde and its formation mechanism seems to involve a charge-transfer reaction pathway. The structure of this compound was fully characterized by LC/DAD-MS and NMR. Its equilibrium forms present in water at different pH values and the respective ionization constants were determined by UV–visible spectroscopy. The results revealed the presence of three equilibria involving only deprotonation reactions at the 7-OH and 4′-OH positions of the pyranoanthocyanin moiety and at the 4′″-OH of the syringol moiety (p K a1 = 3.64 ± 0.01; p K a2 = 8.02 ± 0.01; p K a3 = 11.19 ± 0.01).