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Reaction of Acetaldehyde with Wine Flavonoids in the Presence of Sulfur Dioxide

Sheridan, Marlena K., Elias, Ryan J.
Journal of agricultural and food chemistry 2016 v.64 no.45 pp. 8615-8624
acetaldehyde, anthocyanins, catechin, color, dissolved oxygen, grape seed extract, matrix-assisted laser desorption-ionization mass spectrometry, oxidation, pH, red wines, sulfur dioxide, tannins
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 SO₂ was 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.