OENO IVAS 2019 banner
IVES 9 IVES Conference Series 9 OENO IVAS 9 OENO IVAS 2019 9 Analysis and composition of grapes, wines, wine spirits 9 Identification of cis-2-methyl-4-propyl-1,3-oxathiane as a new volatile sulfur compound (VSC) in wine

Identification of cis-2-methyl-4-propyl-1,3-oxathiane as a new volatile sulfur compound (VSC) in wine

Abstract

Despite their trace concentrations, volatile sulfur compounds (VSCs) are an important category of flavour-active compounds that significantly contribute to desirable or undesirable aromas of many foods and beverages. In wines, VSCs in the form of polyfunctional thiols, notably 3-sulfanylhexan-1-ol (3-SH), 3-sulfanylhexyl acetate (3-SHA), and 4-sulfanyl-4-methyl-pentan-2-one (4-MSP), possess extremely low olfactory thresholds (≈ ng/L) and pleasant “tropical aroma” notes. They have received much attention with respect to their sensory contributions, quantitative occurrences, biogenesis, and thiol management through viticulture and winemaking. However, the fate of these potent volatiles are still not fully understood.

In this work [1], the fate of 3-SH in wine was probed based on the potential sensory and chemistry interactions between 3-SH and acetaldehyde, which led to the identification of cis-2-methyl-4-propyl- 1,3-oxathiane (cis-1) in wine for the first time. Subsequently, a stable isotope dilution assay (SIDA) using headspace–solid-phase microextraction with gas chromatography and mass spectrometry (HS–SPME GC– MS) was developed. A range of parameters was optimised, a deuterated internal standard was synthesised, and the method was fully validated and applied to the quantitation of cis-1 in wines. The aroma detection threshold of 1 was also determined.

The existence of cis-1 in Sauvignon blanc wines from a laboratory-scale fermentation trial was revealed by mass spectral comparison to an authentic standard, linear retention indices of naturally present cis- 1 on two GC columns, and co-injection experiments. Challenges were faced when analysing commercial wine samples due to unknown co-eluting interferences in some wines. After employing d4-1 as the internal standard and evaluating additional capillary column phases, a sensitive SIDA HS–SPME GC–MS method was developed and applied to a survey of commercial wines. Interestingly, trans-1 was not detected whereas cis-1 ranged from undetectable to 460 ng/L, which highly correlated (r = 0.72) to the concentrations of 3-SH, determined in the same wines by HPLC–MS/MS after derivatisation. The aroma detection threshold of 1* in a neutral Australian white wine was found to be 7.1 μg/L. Although cis-1 concentrations in the studied wines were below the odour detection threshold of 1, our results suggest a potential link from cis-1 to the potent VSC 3-SH, and more research is required to gain a better understanding of the importance of cis-1 in wine, from both chemistry and sensory perspectives. The identification and method development work will be presented along with additional experiments involving cis-1 in wine.

references:

[1]. Chen, L., D.L. Capone, and D.W. Jeffery, Identification and Quantitative Analysis of 2-Methyl-4-propyl-1,3-oxathiane in Wine. Journal of Agricultural and Food Chemistry, 2018, 66 (41), 10808–10815.

* Using a commercial standard consisting of 85% cis-1 and 15% trans-1.

DOI:

Publication date: June 23, 2020

Issue: OENO IVAS 2019

Type: Article

Authors

Liang Chen, Dimitra Capone, David Jeffery

The ARC Training Centre for Innovative Wine Production, The University of Adelaide, PMB 1, Glen Osmond, South Australia 5064, Australia 

Contact the author

 

Keywords

wine aroma, tropical fruit, 3-sulfanylhexan-1-ol, stable isotope dilution assay

Tags

IVES Conference Series | OENO IVAS 2019

Citation

Related articles…

Mesoclimate impact on Tannat in the Atlantic terroir of Uruguay

The study of climate is relevant as an element conditioning the typicity of a product, its quality and sustainability over the years. The grapevine development and growth and the final grape and wine composition are closely related to temperature, while climate components vary at mesoscale according to topography and/or proximity to large bodies of water. The objective of this work is to assess the mesoclimate of the Atlantic region of Uruguay and to determine the effect of topography and the ocean on temperature and consequently on Tannat grapevine behavior.

Adaptation to soil and climate through the choice of plant material

Choosing the rootstock, the scion variety and the training system best suited to the local soil and climate are the key elements for an economically sustainable production of wine. The choice of the rootstock/scion variety best adapted to the characteristics of the soil is essential but, by changing climatic conditions, ongoing climate change disrupts the fine-tuned local equilibrium. Higher temperatures induce shifts in developmental stages, with on the one hand increasing fears of spring frost damages and, on the other hand, ripening during the warmest periods in summer. Expected higher water demand and longer and more frequent drought events are also major concerns. The genetic control of the phenotypes, by genomic information but also by the epigenetic control of gene expression, offers a lot of opportunities for adapting the plant material to the future. For complex traits, genomic selection is also a promising method for predicting phenotypes. However, ecophysiological modelling is necessary to better anticipate the phenotypes in unexplored climatic conditions Genetic approaches applied on parameters of ecophysiological models rather than raw observed data are more than ever the basis for finding, or building, the ideal varieties of the future.

Modulation of berry composition by different vineyard management practices

High concentration of sugars in grapes and alcohol in wines is one of the consequences of climate change on viticulture production in several wine-growing regions. In order to investigate the possibilities of adaptation of vineyard management practices aimed to reduce the accumulation of sugar during the maturation phase without reducing the accumulation of anthocyanins in grapes, a study with severe shoot trimming, shoot thinning, cluster thinning and date of harvest was conducted on Merlot variety in Istria region (Croatia), under the Mediterranean climate. Four factors which may affect grape maturation and its composition at harvest were investigated in a two-years experiment; severe shoot trimming applied at veraison when >80% of berries changed colour (in comparison to untreated control), shoot thinning (0 and 30%), cluster thinning (0 and 30%), and the date of harvest (early and standard harvest dates). Shoot thinning had no significant impact on berry composition, despite the obtained reduction in yield per vine. Lower Brix in grapes were obtained with earlier harvest date and if no cluster thinning was applied, although at the same time a reduction in the concentration of anthocyanins in berries was observed in these treatments. On the other hand, if severe shoot trimming was applied when >80% of berries changed colour, a reduction of Brix was obtained without a negative impact on berry anthocyanins concentration. We conclude that in cases when undesirably high sugar concentrations at harvest are expected, severe shoot trimming at 80% veraison may effectively be used in order to obtain moderate sugar concentration in berries together with the adequate phenolic composition.

Spatial determination of areas in the Western Balkans region favorable for organic production

In problematic conditions for production of grapes and wine caused by the COVID-19 pandemic and the resulting occurrence of wine surpluses, producers are increasingly turning to the innovative viticulture and winemaking of products that are more appealing to the market and the consumers. On the other hand, consumption of the food safety or organic products, and therefore of organic grapes and wine, is increasingly common in the world, in particular in Europe. The Regional Rural Development Standing Working Group (SWG RRD), as a regional intergovernmental organization gathers actors in the viticulture and winemaking sector from states and territories of the Western Balkans (South-East Europe) in the Expert Working Group for Wine, with the aim of improving viticulture and winemaking in this region through joint activities. In accordance with the aforementioned, the SWG RRD is working on advancing organic production of grapes and wine, and on recognition of specificities of the terroir of wine-growing areas in Western Balkans. In addition, as part of the project “Facilitation of Exchange and Advice on Wine Regulations in Western Balkan Countries” helmed by the German Federal Ministry of Food and Agriculture, in addition to harmonization of relevant legislation with EU regulations, efforts are being invested towards recognition of organic wines. Within activities and project implemented by this organization, expert analyses and scientific research of the terroir of Western Balkans were carried out, and some of the results are presented in this paper.

Water deficit differentially impacts the performances and the accumulation of grape metabolites of new varieties tolerant to fungi

The use of resistant varieties is a long-term but promising solution to reduce chemical input in viticulture. Several important breeding programs in Europe and abroad are now releasing a range of new hybrids performing well regarding fungi susceptibility and producing good quality wines. Unfortunately, insufficient attention is paid by the breeders to the adaptation of these varieties to climatic changes, notably to the increased climatic demand and water deficit (WD). Thus, prior to the adoption of such varieties by the wine industry in Mediterranean regions, there is a need to consider their suitability to WD. This study aimed to characterize the different drought-strategies adopted by 6 new resistant varieties selected by INRAE in comparison to Syrah. To allow the assessment of long-term impacts of WD, field-grown vines were exposed to contrasted WD from 2018 to 2021 under a semi-arid Mediterranean climate. A gradient of WD was applied in the field and controlled through plant measurements at the single plant level. Grape development was non-destructively monitored to determine the arrest of berry phloem unloading. The impacts of WD on berry composition, including water, primary metabolites (sugars, organic acids), secondary metabolites (anthocyanins, thiols precursors) and main cations contents, were assessed at this specific stage. Results showed different varietal responses during the year and inter-annual acclimation in terms of plant water use efficiency, biomass accumulation, as well as yield components and berry composition. WD differentially reduced the accumulation of primary metabolites at plant and berry levels, but it little changed their concentrations in the fruits at the ripe stage. Moreover, WD differentially impacted the accumulation of secondary metabolites and major cations between the varieties. In the talk, we’ll present the main results regarding the WD impacts on fruit metabolites and enlarge the reflection about the practical assessment of the grapevine acclimation to WD.