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

Marlena K. Sheridan, Ryan J. Elias

Research output: Contribution to journalArticle

13 Citations (Scopus)

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 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.

Original languageEnglish (US)
Pages (from-to)8615-8624
Number of pages10
JournalJournal of agricultural and food chemistry
Volume64
Issue number45
DOIs
StatePublished - Nov 16 2016

Fingerprint

Sulfur Dioxide
Wine
Acetaldehyde
acetaldehyde
sulfur dioxide
Flavonoids
wines
flavonoids
Catechin
catechin
sulfonates
Tannins
Pigments
tannins
Color
Grape Seed Extract
pigments
grape seed extract
malvidin
Anthocyanins

All Science Journal Classification (ASJC) codes

  • Chemistry(all)
  • Agricultural and Biological Sciences(all)

Cite this

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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 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.",
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Reaction of Acetaldehyde with Wine Flavonoids in the Presence of Sulfur Dioxide. / Sheridan, Marlena K.; Elias, Ryan J.

In: Journal of agricultural and food chemistry, Vol. 64, No. 45, 16.11.2016, p. 8615-8624.

Research output: Contribution to journalArticle

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AB - 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.

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