Synthesis of a novel isotopically labelled standard for quantification of γ-nonalactone in New Zealand Pinot noir via SIDA-SPE-GC-MS.

γ-Nonalactone is a linear aliphatic lactone ubiquitous in wine, associated with coconut, sweet, and stone fruit aroma descriptors. Little research has been conducted looking at the importance of this compound to New Zealand (NZ) wine aroma. 2H213C2-γ-Nonalactone, a novel isotopologue of γ-nonalactone, was synthesised in this work for use in a stable isotope dilution assay (SIDA) for quantification of γ-nonalactone in NZ Pinot noir wines for the first time. Synthesis was carried out using heptaldehyde as the starting material, and 13C atoms and 2H atoms were introduced via Wittig olefination and deuterogenation steps, respectively. The suitability of this compound as an internal standard was demonstrated by spiking model wine at normal and elevated conditions during sample preparation, with subsequent analysis via mass spectrometry showing stability of 2H213C2-γ-nonalactone. A model wine calibration, with concentrations of γ-nonalactone from 0 to 100 µg L-1, was shown to have excellent linearity (R2 > 0.99), reproducibility (0.72%), and repeatability (0.38%). Twelve NZ Pinot noir wines, representative of a range of NZ Pinot noir-producing regions, prices, and vintages, were analysed by solid-phase extraction-gas chromatography-mass spectrometry (SPE-GC-MS). The concentrations of γ-nonalactone ranged from 8.3 to 22.5 µg L-1, the latter of which was close to the odour detection threshold of this compound. These findings provide a basis for further research into γ-nonalactone and its impact on NZ Pinot noir aroma and provide a robust method for the quantification of this compound in Pinot noir.

Saturated Linear Aliphatic γ- and δ-Lactones in Wine: A Review.

Saturated linear aliphatic lactones are widespread aroma compounds in wine, linked to stone fruit, dried red fruit, and coconut descriptors. Despite their ubiquity, bioproduction pathways associated with these compounds in wine are unclear, but higher concentrations have been linked to many common vitivinicultural practices, including grape variety, microbiological influence, oak- and bottle-aging, and wine styles such as late harvest, noble rot, and icewine. Development of analytical techniques has enabled increasingly accurate quantification of lactones in wine, shedding more light on their potential origins. This review provides an in-depth summary of the research into linear aliphatic lactones over the past 50 years and provides direction for possible future research to elucidate the biogenesis of these compounds and better estimate their impact on wine aroma.