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


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.


[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.


Publication date: June 23, 2020

Issue: OENO IVAS 2019

Type: Article


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



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


IVES Conference Series | OENO IVAS 2019


Related articles…

“Garrigues”, part of the mediterranean vine terroirs

Les paysages viticoles méditerranéens présentent une originalité qui ne se retrouve nulle part ailleurs : ils associent des garrigues très odoriférantes à des parcelles de vignes souvent qualitatives. La connaissance empirique des vins du Languedoc par leurs dégustateurs a conduit la Chambre d’Agriculture de l’Hérault à supposer que les arômes de la garrigue environnante peuvent se retrouver dans les vins (arômes de ciste, de genévrier, … )

Determination of selected phenolics, carotenoids and norisoprenoids in Riesling grapes after treatment against sunburn damage

Riesling represents the most widely cultivated grape variety in Germany and is therefore of particular economic interest. During recent years an increase in the petrol-note as well as in undesirable bitter and adstringent notes has been reported. These changes are most likely linked to increasing temperature and sunlight exposure of grapes due to climate changes.
The “petrol note” is caused by the formation of the C13-norisoprenoid 1,1,6-trimethyl-1,2-dihydronaphthalin (TDN), which originates from acid-labile precursors formed by the carotenoid degradation in the grape.

Résistance stomatique et caractérisation hydrique des terroirs viticoles

The analysis of the distribution of natural plant populations allows an ecological characterization of cultivated environments in thermal, water and trophic terms; it guides the choice or selection of plants (or grape varieties) to cultivate (Astruc et al ., 1984, 1987; Delpoux, 1971; Jacquinet and Astruc, 1979). This approach has given good results in areas where the topography is the determining factor in the ecological differentiation of the terroirs.

Evaluation of “Accentuated cut edges” technique on the release of varietal thiols and their precursors in Shiraz and Sauvignon blanc wine production

Accentuated cut edges (ACE) is a novel grape crushing technique used sequentially after a conventional crusher to increase the extraction rate and content of polyphenolics, as shown for Pinot noir wine. This inspired us to apply the technique during Shiraz and Sauvignon blanc winemaking, primarily to assess its impact on the extraction of varietal thiol precursors in grape must/juice and formation of varietal thiols in the resultant wines

Lactiplantibacillus plantarum – A versatile tool for biological deacidification

Malolactic fermentation (MLF) is a secondary wine fermentation conducted by lactic acid bacteria (LAB). This fermentation is important in winemaking as it deacidifies the wine, converting L-malic acid into L-lactic acid and carbon dioxide, and it contributes to microbial stability. Wine pH is highly selective, and at pH below 3.5 generally only strains of O. oeni can survive and express malolactic activity, while under more favorable growth conditions above pH 3.5, species of Lactobacillus and Pediococcus may conduct the MLF. Among the LAB species Lactiplantibacillus plantarum strains have shown most interesting results under hot climate conditions, not only for their capacity to induce MLF, but also for their homo-fermentative properties towards hexose sugars, which makes them suitable for induction of MLF in high pH and high alcohol wines, when inoculated at the beginning of alcoholic fermentation.