Macrowine 2021
IVES 9 IVES Conference Series 9 From precursor identification to the study of the distribution of 3-methyl-2,4-nonanedione in red wines and spirits

From precursor identification to the study of the distribution of 3-methyl-2,4-nonanedione in red wines and spirits

Abstract

Prematurely aged red wines are marked by intense prune and fig aromatic nuances that dominate the complex bouquet that can be achieved through bottle aging. This oxidation off-flavor is, in part, caused by the presence of 3-methyl-2,4-nonanedione (MND).1 It is interesting to note that similar aromas are also detected in aged spirits. Despite its strong sensory impact in red wines, the precursors of this diketone were not well described.

So, first investigations were performed in order to quantify this compound in young and aged spirits in order to explain these nuances. In addition, determination of MND precursors in red wines as well as the study of oxidation mechanisms on their evolutions will improve our ability to understand its formation pathway in alcoholic beverages.

The first step of this work aimed at identifying a precursor of MND in grapes and wines. Based on the MND distribution in grapes, in young and old wines we hypothesized that ketols might be precursors of this diketone. We describe the chemical synthesis of 2-hydroxy-3-methylnonan-4-one (syn- and anti-ketol) as well as their identification in wines. MND and ketols were quantified by SPME-GC-MS (CI, MeOH) using SIS and MS/MS mode, respectively, in more than 150 Merlot and Cabernet Sauvignon wines from California, Bordeaux, and Switzerland. Oxidation experiments conducted in model wine and red wine demonstrated that ketols are able to produce MND. Based on these data, their role as MND precursor will be discussed. In addition, we also report first results concerning the origin of ketols in grapes and wines.

We also extended our investigations to spirits were old samples can develop similar dried plum aromas. We also report for the first time the distribution of MND in many spirits including Cognac, Armagnac, Brandy, Bourbon, Grappa, Rhum, Whisky. Highest levels were found in grappa (> 10 000 ng/L), exceeding its detection thresholds (100 ng/L). Sensory analysis experiments revealed that this compound contributes to the aroma of spirits. Assay of ketols in these samples revealed that they can be precursors of MND in spirits.

This project has improved our understanding of the formation and evolution of MND in wines, enabling more accurate predictions of the oxidative behavior and aging potential of red wines. In addition, we describe its first identification as well as its sensory impact in spirits

DOI:

Publication date: September 14, 2021

Issue: Macrowine 2021

Type: Article

Authors

Alexandre PONS

Université Bordeaux, ISVV, EA 4577, Unité de Recherche Œnologie, F-33882 Villenave d’Ornon, France, Seguin Moreau Cooperage, ZI Merpins, 16103 Cognac, France. Ana PETERSON, Université Bordeaux, ISVV, EA 4577, Unité de Recherche Œnologie, F-33882 Villenave d’Ornon, France. Fannie THIBAUD, Université Bordeaux, ISVV, EA 4577, Unité de Recherche Œnologie, F-33882 Villenave d’Ornon, France. Jean Charles MATHURIN, E. Rémy Martin & C°, Z.I, 16100 Merpins, France. Yannick LANDAIS, Université Bordeaux, ISM, CNRS UMR 5255, Talence, France. Philippe DARRIET, Université Bordeaux, ISVV, EA 4577, Unité de Recherche Œnologie, F-33882 Villenave d’Ornon, France. INRA, ISVV, USC 1366, Unité de Recherche Œnologie, F-33882 Villenave d’Ornon, France

Contact the author

Keywords

aging, red wines, oxidation, aroma, spirits, aroma precursor

Citation

Related articles…

Extreme canopy management for vineyard adaptation to climate change: is it a good idea?

Climate change constitutes an enormous challenge for humankind and for all human activities, viticulture not being an exception. Long-term strategic changes are probably needed the most, but growers also need to deal with short-term changes: summers that are getting progressively warmer, earlier harvest dates and higher pH in musts and wines. In the last 10-15 years, a relevant corpus of research is being developed worldwide in order to evaluate to which extent extreme canopy management operations, aimed at reducing leaf area and, thus, limiting the source to sink ratio, could be useful to delay ripening. Although extreme canopy management can result in relevant delays in harvest dates, longer term studies, as well as detailed analysis of their implications on carbohydrate reserves, bud fertility and future yield are desirable before these practices can be recommended.

Effect of partial net shading on the temperature and radiation in the grapevine canopy, consequences on the grape quality of cv. Gros Manseng in PDO Pacherenc-du-vic-Bilh

As elsewhere, southwestern France vineyards face more recurrent summer heat waves these last years. Among the possibilities of adaptation to this climate changing parameter, the use of net shading is a technique that allow for limiting canopy exposure to radiations. In this trial, we tested net shading installed on one face of the canopy, on a north-south row-oriented plot of cv. Gros Manseng trained on VSP system in the PDO Pacherenc-du-Vic-Bilh. The purpose was to characterize the effects on the ambient canopy temperatures and radiations during the season and to observe the consequences on the composition of grapes and wines. Two sorts of net were used with two levels of obstruction (50% and 75%) of the photosynthesis active radiation (PAR). They have been installed on the west side of the canopy and compared to a netless control. Temperature and PAR sensors registered hourly data during the season. On specific summer day (hot and sunny) manual measurements took also place on bunches (temperature) and in different spots of the canopy (PAR). The results showed that, on clear days, the radiation is lowered by the shade nets respecting the supplier criteria. The effects on the ambient canopy temperature were inconstant on this plot when we observed the data from the global period of shading between fruit set and harvest. However, during hot days (>30°C), the temperature in the canopy was reduced during afternoon and the temperature of the bunch surface was reduced as well comparing to the control. A decrease of the maturity parameters of the berries, sugar and acidity, was also observed. Concerning the wine aromatic potential, no differences clearly appeared.

Climate projections over France wine-growing region and its potential impact on phenology

Climate change represents a major challenge for the French wine industry. Climatic conditions in French vineyards have already changed and will continue to evolve. One of the notable effects on grapevine is the advancing growing season. The aim of this study is to characterise the evolution of agroclimatic indicators (Huglin index, number of hot days, mean temperature, cumulative rainfall and number of rainy days during the growing season) at French wine-growing regions scale between 1980 and 2019 using gridded data (8 km resolution, SAFRAN) and for the middle of the 21th century (2046-2065) with 21 GCMs statistically debiased and downscaled at 8 km. A set of three phenological models were used to simulate the budburst (BRIN, Smoothed-Utah), flowering, veraison and theoretical maturity (GFV and GSR) stages for two grape varieties (Chardonnay and Cabernet-Sauvignon) over the whole period studied. All the French wine-growing regions show an increase in both temperatures during the growing season and Huglin index. This increase is accompanied by an advance in the simulated flowering (+3 to +9 days), veraison (+6 to +13 days) and theoretical maturity (+6 to +16 days) stages, which are more noticeable in the north-eastern part of France. The climate projections unanimously show, for all the GCMs considered, a clear increase in the Huglin index (+662 to 771 °C.days compared to the 1980-1999 period) and in the number of hot days (+5.6 to 22.6 days) in all the wine regions studied. Regarding rainfall, the expected evolution remains very uncertain due to the heterogeneity of the climates simulated by the 21 models. Only 4 regions out of 21 have a significant decrease in the number of rainy days during the growing season. The two budburst models show a strong divergence in the evolution of this stage with an average difference of 18 days between the two models on all grapevine regions. The theoretical maturity is the most impacted stage with a potential advance between 40 and 23 days according to wine-growing regions.

δ13C : A still underused indicator in precision viticulture  

The first demonstration of the interest of carbon isotope composition of sugars in grapevine, as an integrated indicator of vineyard water status, dates back to 2000 (Gaudillère et al., 1999; Van Leeuwen et al., 2001). Thanks to the isotopic discrimination of Carbon that takes place during plant photosynthesis, under hydric stress conditions, it is possible to accurately estimate the photosynthetic activity. Ever since, δ13C has been widely applied with success to zonation, terroir studies and vine physiology research, but is still not widely used by viticulturists. This is quite astonishing by considering the impact of global warming on viticulture and the need to improve water management, that would justify a widespread use of δ13C.
The lack of private laboratories proposing the analysis, the cost of the technology, as well as the long analytical delays, have been detrimental to its development. Some laboratories tried to overcome the analytical difficulties of isotopic analysis by using fourier transformed infrared spectroscopy, as a fast and cheap alternative to the official OIV method (IRMS). These claimed FTIR models have never been published or peer reviewed and cannot be considered robust. In this work, thanks to the recent acquisition of IRMS technology, new modern and robust applications of δ13C for viticulture are proposed. This includes the use of the analysis to make parcel separations at harvesting, the possibility to increase the precision of hydric stress cartography and the potential cost reduction when compared with Scholander pressure bomb analysis.

Measurement of redox potential as a new analytical winegrowing tool

Excell laboratory has initiated the development of an analytical method based on electrochemistry to evaluate the ability of wines to undergo or resist to oxidative phenomena. Electrochemistry is a powerful tool to probe reactions involving electron transfers and offers possibility of real-time measurements. In that context, the laboratory has implemented electrochemical analysis to assess oxidation state of different wine matrices but also in order to evaluate oxidative or reduced character of leaf and soil. Initially, our laboratory focused on dosage of compounds involved in responses of plant stresses and we were also interested in microbiological activity of soils. These analyses were compared with the measurement of redox potential (Eh) and pH which are two fundamental variables involved in the modulation of plant metabolism. Indeed, the variation of redox states of the plant reflects its biological activity but also its capacity to absorb nutriments. The Eh-pH conditions mainly determine metabolic processes involved in soil and leaf and our goal is to determine if this combined analytical approach will be sufficiently precise to detect biological evolutions (plant health, parasitic attack…).