41436-47-9Relevant academic research and scientific papers
Fate of damascenone in wine: The role of SO2
Daniel, Merran A.,Elsey, Gordon M.,Capone, Dimitra L.,Perkins, Michael V.,Sefton, Mark A.
, p. 8127 - 8131 (2004)
Damascenone has been shown to undergo reaction with common wine components. Following the action of acid and heat alone, two bicyclic compounds, 4,9,9-trimethyl-8-methylenebicyclo[3.3.1]non-6-en-2-one (2) and 4,4,9-trimethyl-8-methylenebicyclo[3.3.1] non-6-en-2-one (3), were isolated. However, this conversion takes place only very slowly, if at all, under milder conditions (45 °C). When treated with a variety of nucleophiles at pH 3.0 and 5.5, the concentration of damascenone in buffered aqueous ethanol decreased by minor amounts (10-20%) except for cysteine and 2-mercaptoethanol addition at pH 5.5 (～40 and ～30%, respectively) and SO2 (>90% at pH 3.0; 100% at pH 5.5). An adduct from this last combination was prepared and shown to be the C9 sulfonic acid derivative of damascenone. A detailed investigation into the effect of SO2 demonstrated that loss of damascenone in model wine was directly related to the concentration of added SO2 but was essentially unaffected by small changes in pH.
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.
experimental part, 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.
Norisoprenoids in Vitis vinifera White Wine Grapes and the Identification of a Precursor of Damascenone in These Fruits
Sefton, Mark A.,Skouroumounis, George K.,Massy-Westropp, Ralph A.,Williams, Patrick J.
, p. 2071 - 2084 (2007/10/02)
Twenty-four norisoprenoids, which are either free volatile components of juices of Vitis vinifera cvv.Chardonnay, Semillon and Sauvignon Blanc, or are liberated by glycosidase enzyme, or acid hydrolysis of extracts of these juices, have been identified.Eleven of these norisoprenoids are reported as grape products for the first time.The hypothetical 7-oxomegastigmane precursors, grasshopper ketone (5) and megastigm-5-en-7-yne-3,9-diol (10), as well as the related allene, 9-hydroxymegastigma-4,6,7-trien-3-one (6), have been observed for the first time, cooccurring with damascenone (1), 3-hydroxy-β-damascone (2), 3-oxo-β-damascone (3) and 3-oxo-α-damascone (4).Hydrolytic studies have shown that megastigm-5-en-7-yne-3,9-diol (10) is a precursor of damascenone (1) and 3-hydroxy-β-damascone (2) during wine conservation.
Process for preparing 1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-1,3-butanedione and intermediates
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, (2008/06/13)
Described is a process for preparing an equilibrium mixture containing 1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-1,3-butanedione and its enol, which equilibrium mixture contains compounds having the structures: STR1 which process involves first reacting a methyl magnesium halide with 1-acetyl-2,6,6-trimethyl-1,3-cyclohexadiene to form a first organometallic compound; reacting the first organometallic compound with an acetyl halide to form a second organometallic compound, a novel intermediate; and then reacting said second organometallic compound with a hydrolyzing agent such as aqueous acid to form said equilibrium mixture.
1-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-1,3-butanedione and organoleptic uses thereof
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, (2008/06/13)
Processes and compositions are described for the use in tobacco flavor and aroma and perfume aroma augmenting, modifying, enhancing and imparting compositions and as tobacco, perfume, cologne and perfumed article aroma imparting materials of 1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-1,3-butanedione which has the structure: STR1 which also, in its enolate form, has the structure: STR2
