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Rationalizing the Formation of Damascenone: Synthesis and Hydrolysis of Damascenone Precursors and Their Analogues, in Both Aglycone and Glycoconjugate Forms

Rationalizing the Formation of Damascenone: Synthesis and Hydrolysis of Damascenone Precursors and Their Analogues, in Both Aglycone and Glycoconjugate Forms

Merran A Daniel, Carolyn J Puglisi, Dimitra L Capone, Gordon M Elsey, Mark A Sefton

J Agric Food Chem. 2008 Oct 8;56(19):9183-9.

PMID: 18767865

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP23696857	Damascenone		23696-85-7	Price

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