Please use this identifier to cite or link to this item: http://hdl.handle.net/2440/52355
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Type: Journal article
Title: Rationalizing the formation of damascenone: Synthesis and hydrolysis of damascenone precursors and their analogues, in both aglycone and glycoconjugate forms
Author: Daniel, M.
Puglisi, C.
Capone, D.
Elsey, G.
Sefton, M.
Citation: Journal of Agricultural and Food Chemistry, 2008; 56(19):9183-9189
Publisher: Amer Chemical Soc
Issue Date: 2008
ISSN: 0021-8561
1520-5118
Statement of
Responsibility: 
Merran A. Daniel, Carolyn J. Puglisi, Dimitra L. Capone, Gordon M. Elsey and Mark A. Sefton
Abstract: Storage of megastigma-4,6,7-trien-3,9-diol (5), and megastigma-3,4-dien-7-yn-9-ol (6) in aqueous ethanol solution at pH 3.0 and 3.2 gave exclusively damascenone (1) and damascenone adducts at room temperature. The diol (5) had half-lives for the conversion of 32 and 48 h at pH 3.0 and pH 3.2, respectively. The acetylenic alcohol (6) had half-lives of 40 and 65 h at the same pH levels. In order to study the reactivity of the C-9 hydroxyl function in 5 and in the previously investigated allenic triol 2, two model compounds, megastigma-4,6,7-trien-9-ol (7) and megastigma-6,7-dien-9-ol (8) were synthesized. No 1,3-transposition of oxygen to form analogues of damascenone was observed when 7 and 8 were subjected to mild acidic conditions. Such transposition takes place only with highly conjugated acetylenic precursors such as 6 or tertiary allenic alcohols such as 2. The placement of glucose at C-3 of 5 and at C-9 of 6 gave the glycosides 9 and 10, respectively. The effect of such glucoconjugation was to increase the observed half-lives by a factor of only 1.6-1.7 for the allenic glucoside 9, and by 2.1-2.2 for the acetylenic glucoside 10. These studies indicate that the effect of glycosylation on damascenone formation is probably not important on the time scale of wine making and maturation.
Keywords: Damascenone; allenic alcohols; acetylenic alcohols; glycoconjugate; hydrolysis; norisoprenoid; carotenoid metabolites; oxygen transposition.
RMID: 0020083062
DOI: 10.1021/jf8018134
Appears in Collections:Agriculture, Food and Wine publications

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