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Physicochemical Studies of New Anthocyano‐Ellagitannin Hybrid Pigments: About the Origin of the Influence of Oak C ‐Glycosidic Ellagitannins on Wine Color
Author(s) -
Chassaing Stefan,
Lefeuvre Dorothée,
Jacquet Rémi,
Jourdes Michael,
Ducasse Laurent,
Galland Stéphanie,
Grelard Axelle,
Saucier Cédric,
Teissedre PierreLouis,
Dangles Olivier,
Quideau Stéphane
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200901133
Subject(s) - ellagitannin , chemistry , wine , pigment , chromophore , intramolecular force , moiety , tannin , stereochemistry , organic chemistry , polyphenol , food science , antioxidant
Kinetic and thermodynamic UV/Vis and structural NMR spectroscopic investigations on the anthocyano‐ellagitannin hybrid 1‐deoxyvescalagin‐(1β→8)‐oenin revealed that its enhanced color stability relative to that of the red‐colored pigment oenin and resulting bathochromism can be rationalized in terms of an intramolecular π‐stacking between the grape‐derived oenin chromophore and the oak‐derived vescalagin 4,6‐hexahydroxydiphenoyl moiety. The results led us to suggest that this bathochromism‐inducing molecular association could be the first ellagitannin‐based molecular‐level explanation of the red‐to‐purple color change that takes place during the aging of wine in oak barrels.