Evolution of castalagin and vescalagin in ethanol solutions. Identification of new derivatives

Brandies, cognac, armagnac, whiskeys, and rums are aged in oak barrels to improve their organoleptic properties. During this period, numerous compounds such as ellagitannins are extracted from the wood and can subsequently be transformed into new derivatives by chemical reactions. Model solutions of castalagin and vescalagin have been studied to determine the behavior of polyphenols in ethanol-water. Upon prolonged exposure to 40 and 70% (v/v) ethanol at room temperature, hemiketal derivatives containing ethoxy groups have been characterized by LC/MS and NMR. These compounds further evolve to afford the corresponding ketals. They have also been detected in the extracts of oak wood stored under similar conditions.