Quantitative determination of five hydroxy acids, precursors of relevant wine aroma compounds in wine and other alcoholic beverages

The first total syntheses of four stereoisomers of 13‐hydroxy‐14‐methylhexadecanoic acid have been accomplished. Central to this strategy are asymmetric alkynylation of aldehyde, acid‐catalyzed lactonization, the selective protection of primary alcohol and Wittig reaction. The product 1a was obtained in 17 steps in 2% overall yield. Moreover, these synthetic chiral hydroxy fatty acids 1a‐1d are valuable for the development of antibacterial agents.

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“…The data that support the findings of this study are openly available in figshare at http://doi.org/10.1002/chir.23352, reference number [1–43].…”

Section: Data Availability Statementsupporting

confidence: 70%

“…Hydroxy fatty acids are commonly found in seed oils, 1 beer, 2 red wine, 3 and as candidate molecules for determining the type of human‐body odor 4 . Many hydroxy fatty acids exhibit various biological activities and have a wide range of uses.…”

Section: Introductionmentioning

confidence: 99%

Asymmetric syntheses of four stereoisomers of 13‐hydroxy‐14‐methylhexadecanoic acid as potential antibacterial agents

et al. 2021

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“…As different glycosidic precursors of whisky lactones (γ-methyloctalactone) have been described in oak wood [183,184] the presence of some glycosides of the acids cannot be ruled out. In the case of the esters, the corresponding acids have been quantified in unfermented grape must [185].…”

Section: Other Precursors: Molecules Which By Chemical Rearrangement mentioning

confidence: 99%

The Actual and Potential Aroma of Winemaking Grapes

Ferreira

2019

Biomolecules

Self Cite

103

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This review intends to rationalize the knowledge related to the aroma of grapes and to the aroma of wine with specific origin in molecules formed in grapes. The actual flavor of grapes is formed by the few free aroma molecules already found in the pulp and in the skin, plus by those aroma molecules quickly formed by enzymatic/catalytic reactions. The review covers key aroma components of aromatic grapes, raisins and raisinized grapes, and the aroma components responsible from green and vegetal notes. This knowledge is used to explain the flavor properties of neutral grapes. The aroma potential of grape is the consequence of five different systems/pools of specific aroma precursors that during fermentation and/or aging, release wine varietal aroma. In total, 27 relevant wine aroma compounds can be considered that proceed from grape specific precursors. Some of them are immediately formed during fermentation, while some others require long aging time to accumulate. Precursors are glycosides, glutathionyl and cysteinyl conjugates, and other non-volatile molecules.

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“…Few publications had mentioned this topic, and only the esterification path of certain acids during aging had previously been established. 16,17 The quantitative determination of alkyl substituted acids was described many years ago and widely applied in wine. 18,19 However, hydroxycarboxylic acids had received very little attention.…”

Section: ■ Introductionmentioning

confidence: 99%

Study of Substituted Ester Formation in Red Wine by the Development of a New Method for Quantitative Determination and Enantiomeric Separation of Their Corresponding Acids

Lytra

Franc

Cameleyre

et al. 2017

J. Agric. Food Chem.

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A new method was developed for quantifying substituted acids including, where applicable, their various unexplored enantiomeric forms. A new step was added to acids' usual quantification methods, consisting of extraction, derivatization to methyl esters, and gas chromatography analysis: preliminary extraction was performed at basic pH to eliminate ethyl esters, thus avoiding their transesterification during derivatization. Quantitation and enantiomeric distribution of some substituted esters and their corresponding acids were established in 31 commercial Bordeaux red wines from 0 to 20 years old. A strong positive correlation was observed between the age of wine and levels of ethyl 2-methylpropanoate, ethyl 3-methylbutanoate, ethyl 2-methylbutanoate, ethyl (3R)-3-hydroxybutanoate, both enantiomeric forms of ethyl 2-hydroxy-3-methylbutanoate, and ethyl (2S)-2-hydroxy-4-methylpentanoate, but not ethyl (3S)-3-hydroxybutanoate. However, the standard deviations of average concentrations for the corresponding substituted acids were so large that only few correlations between concentrations and age were observed. Concentrations of (2S)-2-hydroxy-3-methylbutanoic acid and (2S)-2-hydroxy-4-methylpentanoic acid increased slightly over time, while (2R)-2-hydroxy-4-methylpentanoic acid levels decreased slightly with the age. Variations in the ratio of substituted ethyl esters to their corresponding acids over time detected thanks to these analytical advances suggested that, in general, acids were continuously esterified during aging.

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Quantitative determination of five hydroxy acids, precursors of relevant wine aroma compounds in wine and other alcoholic beverages

Cited by 22 publications

References 38 publications

Asymmetric syntheses of four stereoisomers of 13‐hydroxy‐14‐methylhexadecanoic acid as potential antibacterial agents

Asymmetric syntheses of four stereoisomers of 13‐hydroxy‐14‐methylhexadecanoic acid as potential antibacterial agents

The Actual and Potential Aroma of Winemaking Grapes

Study of Substituted Ester Formation in Red Wine by the Development of a New Method for Quantitative Determination and Enantiomeric Separation of Their Corresponding Acids

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