title: Reaction of Acetaldehyde with Wine Flavonoids in the Presence of Sulfur Dioxide.
abstract: Acetaldehyde is responsible for many of the beneficial changes that occur in red wine as a result of oxidation. Ethylidene bridges are formed between flavonoids upon their reaction with acetaldehyde, which can contribute to improvements in color stability and SO2-resistant pigments. In the present study, the reactions between acetaldehyde and various flavonoids (catechin, tannins from grape seed extract, and malvidin-3-glucoside) were examined in a model wine system. Lower pH conditions were seen to significantly increase the rate of reaction with acetaldehyde, whereas dissolved oxygen did not affect the rate. In systems containing SO2, the rate of reaction of acetaldehyde with catechin was slowed but was not prevented until SO2was in great excess. Significant improvements in color stability were also observed after treatment with acetaldehyde, despite the presence of equimolar SO2. These results demonstrate that acetaldehyde is reactive in its sulfonate form, which is contrary to widely held assumptions. In addition, the products of the reaction of flavonoids with acetaldehyde were characterized using MALDI-TOF MS in this study. Ethyl-bridged catechin nonamers were observed, as well as anthocyanin and pyranoanthocyanin derivatives of catechin and tannin oligomers. The results of this work illustrate the significance of acetaldehyde reactions in forming stable pigments in wine and the reactivity of acetaldehyde from its sulfonate form.
authors.affiliation: Department of Food Science, College of Agricultural Sciences, The Pennsylvania State University , University Park, Pennsylvania 16802, United States.
authors.forename: Marlena K
authors.initials: MK
authors.lastname: Sheridan
authors.affiliation: Department of Food Science, College of Agricultural Sciences, The Pennsylvania State University , University Park, Pennsylvania 16802, United States.
authors.forename: Ryan J
authors.initials: RJ
authors.lastname: Elias
mesh_terms: D000079:Acetaldehyde / Q000737:chemistry*; D000872:Anthocyanins / Q000737:chemistry; D005419:Flavonoids / Q000737:chemistry*; D007700:Kinetics; D013058:Mass Spectrometry; D010084:Oxidation-Reduction; D013458:Sulfur Dioxide / Q000737:chemistry*; D014920:Wine / Q000032:analysis*
chemical_list: D000872:Anthocyanins; D005419:Flavonoids; D013458:Sulfur Dioxide; D000079:Acetaldehyde
keywords: acetaldehyde; anthocyanin; flavonoid; sulfur dioxide; tannin; wine oxidation