Please use this identifier to cite or link to this item: http://hdl.handle.net/2440/55318
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Type: Journal article
Title: Fate of Damascenone in Wine: The Role of SO2
Author: Daniel, M.
Elsey, G.
Capone, D.
Perkins, M.
Sefton, M.
Citation: Journal of Agricultural and Food Chemistry, 2004; 52(26):8127-8131
Publisher: Amer Chemical Soc
Issue Date: 2004
ISSN: 0021-8561
1520-5118
Statement of
Responsibility: 
Merran A. Daniel, Gordon M. Elsey, Dimitra L. Capone, Michael V. Perkins and Mark A. Sefton
Abstract: Damascenone has been shown to undergo reaction with common wine components. Following the action of acid and heat alone, two bicyclic compounds, 4,9,9-trimethyl-8-methylenebicyclo[3.3.1]non-6-en-2-one (2) and 4,4,9-trimethyl-8-methylenebicyclo[3.3.1] non-6-en-2-one (3), were isolated. However, this conversion takes place only very slowly, if at all, under milder conditions (45 °C). When treated with a variety of nucleophiles at pH 3.0 and 5.5, the concentration of damascenone in buffered aqueous ethanol decreased by minor amounts (10−20%) except for cysteine and 2-mercaptoethanol addition at pH 5.5 (40 and 30%, respectively) and SO2 (>90% at pH 3.0; 100% at pH 5.5). An adduct from this last combination was prepared and shown to be the C9 sulfonic acid derivative of damascenone. A detailed investigation into the effect of SO2 demonstrated that loss of damascenone in model wine was directly related to the concentration of added SO2 but was essentially unaffected by small changes in pH.
Keywords: Damascenone; sulfur dioxide; sulfonic acid; nucleophilic components; degradation; bicyclodamascenone
Description: Copyright © 2004 American Chemical Society
RMID: 0020092549
DOI: 10.1021/jf048582h
Appears in Collections:Agriculture, Food and Wine publications

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