Malvidin-3‑O‑glucoside Chemical Behavior in the Wine pH Range

Anthocyanins are natural pigments responsible for the typical color of red wines and are critically associated with the wine commercial value and longevity. Thus, understanding the molecular bases of the anthocyanin chemical behavior in the complex wine environment is a central issue to the enological sector. By setting up a nuclear-magnetic-resonance-based experimental protocol, new important insights into the chemistry of malvidin-3-O-glucoside, a major wine anthocyanin, in model solution have been provided. Two new equilibrating isomers of the anthocyanin have been identified and quantified at typical wine pH values. More importantly, the key role of pH in determining the solubility and co-pigmentation process of malvidin-3-O-glucoside has been clarified. Consequently, a value of pH of about 3.3 or lower favors co-pigmentation while inhibiting the precipitation of significant quantities of anthocyanins during the maceration−extraction phase of the winemaking.