Distribution and Organoleptic Impact of Ethyl 2-Methylbutanoate Enantiomers in Wine

The enantiomers of ethyl 2-methylbutanoate were assayed in several wines using chiral gas chromatography (beta-cyclodextrin). Analyses of 37 commercial red wines from various vintages and origins revealed the almost exclusive presence of the S-enantiomeric form. The average concentration was similar to 50 mu g/L, but the oldest samples were found to contain higher ethyl 2-methylbutanoate levels than the youngest wines. The olfactory threshold of a racemic mixture of ethyl (2R)-2-methylbutanoate and ethyl (2S)-2-methylbutanoate (50:50, m/m) in dilute alcohol solution was 2.60 mu g/L, almost twice that of the S-form, which was 1.53 mu g/L. Ethyl (2S)-2-methylbutanoate and the racemic mixture of ethyl (2R)-2-methylbutanoate and ethyl (2S)-2-methylbutanoate had different aromatic nuances: the former was mainly defined by fruity descriptors, such as green apple (Granny Smith) and strawberry, whereas the latter had an unspecific, caustic, fruity, solvent odor. Sensory analysis revealed an enhancing effect of ethyl (25)-2-methylbutanoate on the perception of fruity aromas in the matrices studied: the olfactory threshold of the fruity pool, consisting of esters found in red wines, in dilute alcohol solution alone was higher than that of the same mixture supplemented with 50 mu g/L ethyl (2S)-2-methylbutanoate. The sensory profiles of these aromatic reconstitutions highlighted the contribution of ethyl (2S)-2-methylbutanoate to black-berry-fruit descriptors.