Fate of Damascenone in Wine:  The Role of SO2

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. Keywords: Damascenone; sulfur dioxide; sulfonic acid; nucleophilic components; degradation; bicyclodamascenone