Identification and analysis of piperitone in red wines

•A new terpene called piperitone has been identified in red wines.•Optimization of preparative gas chromatography analysis for purification.•Detection threshold: 0.9 μg/L in wine model solution and 70 μg/L in red wine.•Detected mainly in red wine as (4R)-(−)-piperitone.•Concentrations ranged from some ng/L to 435 ng/L.

The present study concerns the search for new aroma compounds associated with the flavor of aged and prematurely aged red wines. Sensory descriptive analysis associated with gas chromatography–olfactometry was first performed to find specific odoriferous zones. One of the zones, reminiscent of mint, was found in red wines with a prune flavor. Thanks to several analytical approaches including preparative gas chromatography, p-menth-1-en-3-one (piperitone), has been identified in red wines. The olfactory detection threshold of this terpene reminiscent of mint was 0.9 μg/L in model hydroalcoholic solution and 70 μg/L in red wines. Chiral multidimensional GC–MS was used to show that piperitone was present mainly in the (R) form in red wines. The concentration of piperitone in aged red wines ranged from a few ng/L to 435 ng/L, but the level was not linked to the age of the wine nor to its premature evolution.