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https://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. |
DOI: | 10.1021/jf8018134 |
Published version: | http://dx.doi.org/10.1021/jf8018134 |
Appears in Collections: | Agriculture, Food and Wine publications Aurora harvest 5 |
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