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https://hdl.handle.net/2440/52355
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DC Field | Value | Language |
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dc.contributor.author | Daniel, M. | - |
dc.contributor.author | Puglisi, C. | - |
dc.contributor.author | Capone, D. | - |
dc.contributor.author | Elsey, G. | - |
dc.contributor.author | Sefton, M. | - |
dc.date.issued | 2008 | - |
dc.identifier.citation | Journal of Agricultural and Food Chemistry, 2008; 56(19):9183-9189 | - |
dc.identifier.issn | 0021-8561 | - |
dc.identifier.issn | 1520-5118 | - |
dc.identifier.uri | http://hdl.handle.net/2440/52355 | - |
dc.description.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. | - |
dc.description.statementofresponsibility | Merran A. Daniel, Carolyn J. Puglisi, Dimitra L. Capone, Gordon M. Elsey and Mark A. Sefton | - |
dc.language.iso | en | - |
dc.publisher | Amer Chemical Soc | - |
dc.source.uri | http://dx.doi.org/10.1021/jf8018134 | - |
dc.subject | Damascenone | - |
dc.subject | allenic alcohols | - |
dc.subject | acetylenic alcohols | - |
dc.subject | glycoconjugate | - |
dc.subject | hydrolysis | - |
dc.subject | norisoprenoid | - |
dc.subject | carotenoid metabolites | - |
dc.subject | oxygen transposition. | - |
dc.title | Rationalizing the formation of damascenone: Synthesis and hydrolysis of damascenone precursors and their analogues, in both aglycone and glycoconjugate forms | - |
dc.type | Journal article | - |
dc.identifier.doi | 10.1021/jf8018134 | - |
pubs.publication-status | Published | - |
dc.identifier.orcid | Capone, D. [0000-0003-4424-0746] | - |
Appears in Collections: | Agriculture, Food and Wine publications Aurora harvest 5 |
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