Macrowine 2021
IVES 9 IVES Conference Series 9 Red wine substituted esters involved in fruity aromatic expression: an enantiomeric approach to understand their sensory impact and their pathway formation

Red wine substituted esters involved in fruity aromatic expression: an enantiomeric approach to understand their sensory impact and their pathway formation

Abstract

Among red wines ethyl esters, those from short hydroxylated and branched-chain aliphatic acids constitute a family with a particular behavior and sensory importance. They have been previously discussed in the literature [1] and recent studies have established that some of them were strongly involved in of red wines’ fruity aroma [2]. As some among them have an asymmetrical carbon atom, it seemed important to separate their different enantiomers to obtain an accurate assessment of their organoleptic impact. Three chiral esters have been identified, presenting alkyl and/or hydroxyle substituants: ethyl 2-hydroxy-4-methylpentanoate, ethyl 2-methylbutanoate, and ethyl 3-hydroxybutanoate. They were present in wines with a single or both enantiomeric forms in various ratios, according to age. On the contrary of most of the ethyl esters, produced during alcoholic fermentation, these esters levels increased gradually over time and then stabilize after about four to five years. For those present under two enantiomeric forms, ratios were modified during ageing. For each ester of this type, the most powerful enantiomer, from an olfactive point of view, was found in relatively small amount at the end of alcoholic fermentation and was then particularly accumulated. The sensorial role of these chiral compounds has been established, revealing their role as natural enhancers of black-berry, red-berry and fresh-fruit aromas. Our data corroborate and specify those of Lytra et al. [2] and Pineau et al. [3] highlighting the impact of substituted esters in fruity expression of red wines. Considering their dynamic evolution of their concentration, these compounds seem to be produced on one hand during alcoholic fermentation by Saccharomyces cerevisiae from amino acids and on the other hand during aging by a chemical esterification from the corresponding substituted acids as previously suggested by Diaz-Maroto et al. [4]. In order to determine the precursors of these esters and to consider synthesis pathways, we have developed a method aimed at quantifying their corresponding substituted acids (2-hydroxy-4-methylpentanoic acid, 2-methylbutanoic acid, and 3-hydroxybutanoic acid) including, if applicable, the enantiomeric forms. Thanks to the quantification of these compounds, the chemical formation of substituted esters during aging as well as the mechanisms of formation of these compounds during alcoholic and malolactic fermentation was described.

References: 1. Guth, H. (1997) J. Agric. Food Chem.45:3027-3032. 2. Lytra, G., Tempere, S., Le Floch, A., de Revel, G., and Barbe, J.-C. (2013) J. Agric. Food Chem. 61:8504-8513. 3. Pineau, B., Barbe, J.-C., Van Leeuwen, C., Dubourdieu, D. (2009) J. Agric. Food Chem. 57:3702-3708. 4. Diaz-Maroto, M.C., Schneider, R., Baumes, R. (2005) J. Agric. Food Chem. 53: 3503-3509.

Publication date: May 17, 2024

Issue: Macrowine 2016

Type: Article

Authors

Georgia Lytra*, Jean-Christophe Barbe, Margaux Cameleyre, Sophie Tempère

*Université de Bordeaux

Contact the author

Tags

IVES Conference Series | Macrowine | Macrowine 2016

Citation

Related articles…

Evaluation of colloidal stability in white and rosé wines investing Dynamic Light Scattering technology

Proteins constitute one of the three main components of grape juice and white wine, phenolic compounds and polysaccharides being the others. A specific group of the total grape-derived proteins resists degradation or adsorption during the winemaking process and remains in finished wine if not removed by the commonplace commercial practice of bentonite fining. While bentonite is effective in removing the problematic proteins, it is claimed to adversely affect the quality of the treated wine under certain conditions, through the removal of colour, flavor and texture compounds. A number of studies have indicated that different protein fractions require distinct bentonite concentrations for protein removal and consequent heat stabilization.

Moscatel vine-shoot extracts as grapevine biostimulant to increase the varietal aroma of Airén wines

There is a growing interest in the exploitation of vine-shoots waste, since they are often left or burned. Sánchez-Gómez et al. [1] have shown that vines-shoots aqueous extracts have significant contents of bioactive compounds, among which several polyphenols and volatiles are highlighted. Recent studied had demonstrated that the chemical composition of vine-shoots is enhanced when vine-shoots are toasted
[2,3]. The application of vegetable products in the vineyards has led to significant changes towards a more “Sustainable Viticulture”. An innovative foliar application for Airén vine-shoot extracts have been carried out to the vineyard. It has been shown that they act as grape biostimulants, improving certain wine quality characteristics [4].

Simultaneous monitoring of dissolved CO2 and collar from Rosé sparkling wine glasses: the impact of yeast macromolecules

Champagne or sparkling wines elaborated through the same traditional method, which consists in two major yeast-fermented steps, typically hold about 10 to 12 g/L of dissolved CO2 after the second fermentation in a closed bottle. Hundreds of molecules and macromolecules originating from grape and yeast cohabit with dissolved CO2; they are essential compounds contributing to many organoleptic characteristics (effervescence, foam, aroma, taste, colour…). Indeed, the second alcoholic fermentation and the maturation on lees (which may last from 12 months up to several years) both induce various quantitative and qualitative changes in the wine through the action of yeast, as listed hereafter: development of aromas during aging on lees, release of nitrogen compounds during autolysis and release of macromolecules (polysaccharides, lipids, nucleic acids) in wine.

Use of computational modelling for selecting adsorbents for improved fining of wine

The occurrence of faults and taints in wine, such as those caused by microbial spoilage or various taints, have resulted in significant financial losses to wine producers. The wine industry commits significant financial resources towards fining and taint removal processes each year. Fining involves the addition of one or more adsorptive substrates to juice or wine to bind certain components, thus reducing their concentration [1]. However, these processes are often not selective and can also remove desirable flavour and aroma compounds.

Impact of non-fruity compounds on red wines fruity aromatic expression: the role of higher alcohols

A part, at least, of the fruity aroma of red wines is the consequence of perceptive interactions between various aromatic compounds, particularly ethyl esters and acetates, which may contribute to the perception of fruity aromas, specifically thanks to synergistic effects.1,2 The question of the indirect impact of non-fruity compounds on this particular aromatic expression has not yet been widely investigated. Among these compounds higher alcohols (HA) represent the main group, from a quantitative standpoint, of volatiles in many alcoholic beverages. Moreover, some bibliographic data suggested their contribution to the aromatic complexity by either increasing or masking flavors of wine, depending of their concentrations.