23726-93-4Relevant articles and documents
Thermal oxidation of 9′-cis-neoxanthin in a model system containing peroxyacetic acid leads to the potent odorant β-damascenone
Bezman, Yair,Bilkis, Itzhak,Winterhalter, Peter,Fleischmann, Peter,Rouseff, Russell L.,Baldermann, Susanne,Naim, Michael
, p. 9199 - 9206 (2005)
The potent odorant β-damascenone was formed directly from 9′-cis-neoxanthin in a model system by peroxyacetic acid oxidation and two-phase thermal degradation without the involvement of enzymatic activity. β-Damascenone formation was heavily dependent on pH (optimum at 5.0) and temperature, occurring over the two sequential phases. The first was incubation with peroxyacetic acid at 60°C for 90 min, and the second was at above 90°C for 20 min. Only traces of β-damascenone were formed on application of only one of the two phases. Formate and citrate solutions produced a much better environment for β-damascenone formation than acetate and phosphate. About 7 μg/L β-damascenone was formed from 5.8 mg/L 9′-cis-neoxanthin under optimal experimental condition. The detailed pathway by which β-damascenone is formed remains to be elucidated.
Rationalizing the formation of damascenone: Synthesis and hydrolysis of damascenone precursors and their analogues, in both aglycone and glycoconjugate forms
Daniel, Merran A.,Puglisi, Carolyn J.,Capone, Dimitra L.,Elsey, Gordon M.,Sefton, Mark A.
scheme or table, p. 9183 - 9189 (2010/04/23)
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.
New preparation methods for α-damascone, γ-damascone, and β-damascenone using pyronenes
Boulin, Bertrand,Taran, Martine,Miguel, Bernadette Arreguy-San,Delmond, Bernard
, p. 2579 - 2591 (2008/02/10)
γ- and δ-Pyronenes are terpenic synthons easily available from myrcene. They are used as intermediates in the synthesis of α-damascone, γ-damascones, and β-damascenone. Copyright Taylor & Francis Group, LLC.