Synthesis, Isolation, Structure Elucidation, and Color Properties of 10-Acetyl-pyranoanthocyanins

Grape anthocyanins reacted with diacetyl, a secondary metabolite of microorganisms involved in winemaking, to form 10-acetyl-pyranoanthocyanins, a type of anthocyanin-derived pigment similar to other vitisin-type pyranoanthocyanins found in red wines. The structures of 10-acetyl-pyranomalvidin-3-β-O-glucoside and 10-acetyl-pyranopeonidin-3-β-O-glucoside were confirmed by spectroscopic methods (UV–vis, MS/MS, and NMR) after their synthesis and isolation. In contrast to other vitisin-type pyranoanthocyanins, the newly described 10-acetyl-pyranoanthocyanins exhibited differentiated color-related properties. They showed an important tendency to occur as colorless hemiacetals at C-10 under wine pH conditions, while co-occurrence of flavylium cation and quinoidal base yielded a broad visible absorbance band around 510–520 nm. Moreover, they easily reacted with bisulfite in acidic aqueous solution (pH 2.0), but the expected bleaching was not observed. Bisulfite bonded to the carbonyl of 10-acetyl substituent ins...