The premature aging of red Vitis vinifera L. wines is mainly associated with the formation of an intense off-flavor reminiscent of prunes. The compounds responsible for this deterioration in red wine flavor have not previously been identified. Sensory descriptive analysis associated with a gas chromatography-olfactometry (GC-O) technique was first performed to find characteristic odoriferous zones of 15 aged red wines with or without a marked prune aroma. Afterward, high-pressure liquid chromatography, gas chromatography, and multidimensional gas chromatography coupled with mass spectrometry (MDGC-MS) were used to identify the odorants reminiscent of prunes in prematurely aged red wines and in the dried fruit. Three compounds were detected with a strong odor of prunes: gamma-nonalactone, beta-damascenone, and 3-methyl-2,4-nonanedione. The perception threshold of the latter beta-diketone in a model hydroalcoholic solution is 16 ng/L. Identified for the first time in aged red wines, this very powerful volatile compound was also suggested to produce the characteristic prune aroma of prematurely aged red wines. The presence of 3-methyl-2,4-nonanedione was also detected in prunes for the first time.
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