Journal of Agricultural and Food Chemistry 2012-02-15

Synthesis and structural characterization of oaklin-catechins.

André Sousa, Ana Fernandes, Nuno Mateus, Victor De Freitas

Index: J. Agric. Food Chem. 60(6) , 1528-34, (2012)

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Abstract

Condensation reactions of procyanidin dimer B4 with two representative oak wood cinnamic aldehydes (coniferaldehyde and sinapaldehyde) were conducted in winelike model solutions. Coniferaldehyde led to the formation of guaiacylcatechin-pyrylium-catechin (GCP-catechin, 737 m/z), whereas sinapaldehyde led to the formation of syringylcatechin-pyrylium-catechin (SCP-catechin, 767 m/z). The former was also structurally characterized by 1D and 2D NMR, allowing an elucidation of the formation mechanism of these oaklin-catechin adducts and demonstrating the importance of procyanidins in the formation of colored compounds through the reaction with cinnamic aldehydes extracted from oaks during storage.