terclim by ICS banner
IVES 9 IVES Conference Series 9 OPTIMIZING THE IDENTIFICATION OF NEW THIOLS AT TRACE LEVEL IN AGED RED WINES USING NEW OAK WOOD FUNCTIONALISATION STRATEGY

OPTIMIZING THE IDENTIFICATION OF NEW THIOLS AT TRACE LEVEL IN AGED RED WINES USING NEW OAK WOOD FUNCTIONALISATION STRATEGY

Abstract

During bottle aging, many thiol compounds are involved in the expression of bouquet of great aged red wines according to the quality of the closure.1,2 Identifying thiol compounds in red wines is a challenging task due several drawbacks including, the complexity of the matrix, the low concentration of these impact compounds and the amount of wine needed.3,4

This work aims to develop a new strategy based on the functionalisation of oak wood organic extracts with H₂S, to produce new thiols, in order to mimic what can happen in red wine during bottle aging. Following this approach and through sensory analysis experiments, we demonstrated that the vanilla-like aroma of fresh oak wood was transformed into intense “meaty” nuances similar to those found in old but non oxidized red wines.5 Functionalized samples were analysed by gas chromatography coupled with a pulsed flame photometric detector (GC-PFPD) and olfactometry (GC-O) to optimize the reaction conditions. Analysis of functionalized oak wood organic extracts by GC-O and GC-PFPD led us to detect six OZ reminiscent of “meaty” nuances and associated with sulphur compounds. One of them was characterized by preparative multi-dimensional gas chromatography coupled with olfactometry and time of flight mass spectrometry (Prep-MDGC-O-TOF MS) and identified as 2-methoxybenzenethiol.

This thiol was also identified in red wines following extraction by SPE, separation and detection by means of GC-MS/MS (SRM mode). The validation of the quantification method was carried out before its use to study its distribution in wines, young and old from different appellations and according to the OTR (determined by coulometry) of the closure. We show that its concentration can reach the odour detection threshold determined at 607 ng/L. Following the same strategy, five other thiols reminiscent of “meaty” nuances, including 2,5-dimethylfuran-3-thiol, 5-methyl-2-furfurylthiol, o-toluenethiol, 2,6-dimethylbenzenethiol and 2,6-dimethoxybenzenethiol were also identified for the first time in red wines. Their sensory impact will also be discussed.

 

1. Picard, M.; Thibon, C.; Redon, P.; Darriet, P.; de Revel, G.; Marchand, S. Involvement of Dimethyl Sulfide and Several Polyfunctional Thiols in the Aromatic Expression of the Aging Bouquet of Red Bordeaux Wines. J. Agric. Food Chem. 2015, 63 (40), 8879–8889. https://doi.org/10.1021/acs.jafc.5b03977.
2. Pons, A.; Lavigne, V.; Suhas, E.; Thibon, C.; Redon, P.; Loisel, C.; Darriet, P. Impact of the Closure Oxygen Transfer Rate on Volatile Compound Composition and Oxidation Aroma Intensity of Merlot and Cabernet Sauvignon Blend: A 10 Year Study. J. Agric. Food Chem. 2022, 70 (51), 16358–16368. https://doi.org/10.1021/acs.jafc.2c07475.
3. Pons, A.; Lavigne, V.; Eric, F.; Darriet, P.; Dubourdieu, D. Identification of Volatile Compounds Responsible for Prune Aroma in Prematurely Aged Red Wines. J. Agric. Food Chem. 2008, 56 (13), 5285–5290. https://doi.org/10.1021/jf073513z.
4. Chen, L.; Darriet, P. Strategies for the Identification and Sensory Evaluation of Volatile Constituents in Wine. Compr. Rev. Food Sci. Food Saf. 2021, 20 (5), 4549–4583. https://doi.org/10.1111/1541-4337.12810.
5. Picard, M.; Tempere, S.; de Revel, G.; Marchand, S. A Sensory Study of the Ageing Bouquet of Red Bordeaux Wines: A Three-Step Approach for Exploring a Complex Olfactory Concept. Food Qual. Prefer. 2015, 42, 110–122. https://doi.org/10.1016/j. foodqual.2015.01.014.

DOI:

Publication date: February 9, 2024

Issue: OENO Macrowine 2023

Type: Article

Authors

Emilie Suhas1,2,4, Svitlana Shinkaruk1,2, Alexandre Pons1,2,3

1. Univ. Bordeaux, Bordeaux INP, INRAE, OENO, UMR 1366, ISVV, F-33140 Villenave d’Ornon, France
2. Bordeaux Sciences Agro, Bordeaux INP, INRAE, OENO, UMR 1366, ISVV, F-33170 Gradignan, France
3. Seguin Moreau France, Z.I. Merpins, BP 94, 16103 Cognac, France
4. Diam bouchage, Céret 66400, France

Contact the author*

Keywords

Red wines, Thiol compounds, Meaty aroma, Oak wood functionalisation strategy

Tags

IVES Conference Series | oeno macrowine 2023 | oeno-macrowine

Citation

Related articles…

IMPACT OF GRAPE-ASSOCIATED MOLDS IN FRESH MUSHROOM AROMA PRODUCTION

Mycobiota encountered from vine to wine is a complex and diversified ecosystem that may impact grape quality at harvest and the sensorial properties of wines, thus leading to off-flavors [1-3]. Among known off-flavors in wine, fresh mushroom aroma (FMA) has been linked to some mold species, naturally pre-sent on grapes, producing specific volatile organic compounds (VOC) [4-5]. The most well-known are 1-octen-3-ol and 1-octen-3-one, although many other VOC are likely involved. To better understand the FMA defect, biotic and abiotic factors impacting growth kinetics and VOC production of selected fungal species in must media and on grapes were studied.
Read More

PHOTOCHEMICAL DEGRADATION OF TRYPTOPHAN IN MODEL WINE: IMPACT OF HEAVY METALS AND OXYGEN ON 2-AMINOACETOPHENONE FORMATION

The wine industry worldwide faces more and more challenges due to climate change, such as increased dryness in some areas, water stress, sunburn and early harvesting during hot summer temperatures¹. One of the resulting problems for the wine quality might be a higher prevalence of the untypical aging off-flavor (ATA)². A substance, which Rapp and Versini made responsible for ATA, is the 2-aminoace-tophenone (2-AAP)³. 2-AAP in wine causes a naphthalene, wet towels, wet wool, acacia flower or just a soapy note⁴.

Read More

UNEXPECTED PRODUCTION OF DMS POTENTIAL DURING ALCOOLIC FERMENTATION FROM MODEL CHAMPAGNE-LIKE MUSTS

The overall quality of aged wines is in part due to the development of complex aromas over a long period (1.) The apparition of this aromatic complexity depends on multiple chemical reactions that include the liberation of odorous compounds from non-odorous precursors. One example of this phenomenon is found in dimethyl sulphide (DMS) which, with its characteristic odor truffle, is a known contributor to the bouquet of premium aged wine bouquet (1). DMS supposedly accumulates during the ten first years of ageing thanks to the hydrolysis of its precursor dimethylsulfoniopropionate (DMSp.) DMSp is a possible secondary by-product from the degradation of S-methylmethionine (SMM), an amino acid iden- tified in grapes (2), which can be metabolized by yeast during alcoholic fermentation.

Read More

UNRAVELING THE CHEMICAL MECHANISM OF MND FORMATION IN RED WINE DURING BOTTLE AGING : IDENTIFICATION OF A NEW GLUCOSYLATED HYDROXYKETONE PRO-PRECURSOR

During bottle aging, the development of wine aroma through low and gradual oxygen exposure is often positive in red wines, but can be unfavorable in many cases, resulting in a rapid loss of fresh, fruity flavors. Prematurely aged wines are marked by intense prune and fig aromatic nuances that dominate the desirable bouquet achieved through aging (Pons et al., 2013). This aromatic defect, in part, is caused by the presence of 3-methyl-2,4-nonanedione (MND). MND content was shown to be lower in nonoxidized red wines and higher in oxidized red wines, which systematically exceeds the odor detection threshold (62 ng/L).

Read More

IMPACT OF CLIMATIC CONDITIONS ON THE SEASONING QUALITY OF OAK WOOD FOR OENOLOGICAL USE (QUERCUS PETRAEA)

For coopers, seasoning and toasting are considered crucial steps in barrel making during which the oak wood develops specific organoleptic properties. Seasoning, carried out in the open air, allows reducing the moisture content of the staves to between 14 and 18% (compared to 70 to 90% after splitting) while modulating the intrinsic composition of the oak wood. Toasting consists of applying different degrees of heat to a barrel for a specific period of time. As the temperature increases, oak wood produces a wide range of chemical compounds through thermal degradation of its intrinsic composition.

Read More