Synthesis of alkyl sulfonic acid aldehydes and alcohols, putative precursors to important wine aroma thiols

Duhamel, Nina; Piano, Federico; Davidson, Samuel J.; Larcher, R.; Fedrizzi, Bruno; Barker, David

doi:10.1016/j.tetlet.2015.02.084

Cited by 16 publications

(7 citation statements)

References 27 publications

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“…Liberation of 3SH during fermentation has been shown for the GSH conjugate (via reversion to GSH-3SHal and enzymatic carbonyl reduction to yield the primary alcohol) but not for the adducts of (E)-2-hexenal or mesityl oxide. alternative precursors to 3SH and 4MSP [34] (Fig. 2).…”

Section: Analysis Of Varietal Thiols In Juice and Winementioning

confidence: 99%

Spotlight on Varietal Thiols and Precursors in Grapes and Wines

Jeffery¹

2016

Aust. J. Chem.

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Wine is an amazingly complex natural product that requires dedicated scientists to resolve many of its mysteries. Traditional synthetic organic chemistry and modern analytical techniques are powerful tools at the disposal of wine chemists who tackle the complexities of wine in order to improve scientific understanding and provide practical solutions to industry. Part of this quest for knowledge relates to maintaining or improving wine quality, which underpins consumer acceptance and links to the competitiveness of wineries in a global market. Wine aroma is an important aspect of wine quality and garners much attention from researchers. Grape-derived aroma compounds are one area of particular importance owing to their distinctiveness and ability to impart 'varietal aromas' to wines. Varietal thiols imparting tropical and citrus notes that are characteristic of wines such as Sauvignon Blanc have emerged, along with their grape-derived precursors, as an area of interest over the past two decades. These compounds have also caught our attention and we have made some important contributions to this field, including identifying new precursors, developing novel analytical methods, and conducting studies that provide unique insights into the biochemical transformations occurring in grape berries and juice, and during fermentation.

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Section: Analysis Of Varietal Thiols In Juice and Winementioning

confidence: 99%

Spotlight on Varietal Thiols and Precursors in Grapes and Wines

Jeffery¹

2016

Aust. J. Chem.

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“…G3Shal has been identified in grape juice, and even post-fermentation in finished wines [ 44 , 69 , 82 ]. One characteristic of aldehydes is their tendency to react with bisulfite or sulfur dioxide to form the corresponding sulfonic acids [ 83 , 84 , 85 ]. In fact, it has long been suggested that most aldehyde-containing compounds found in wine exist in an equilibrium between the carbonyl and sulfonic acid forms (such as the equilibrium shown in step B of Scheme 6 ) [ 84 ].…”

Section: Further Exploration Of the Pathways To 3shmentioning

confidence: 99%

Unraveling the Mystery of 3-Sulfanylhexan-1-ol: The Evolution of Methodology for the Analysis of Precursors to 3-Sulfanylhexan-1-ol in Wine

Muhl

Pilkington

Fedrizzi

et al. 2022

Foods

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Volatile polyfunctional thiol compounds, particularly 3-sulfanylhexan-1-ol (3SH) and 3-sulfanylhexyl acetate (3SHA), are key odorants contributing to the aroma profile of many wine styles, generally imparting tropical grapefruit and passionfruit aromas. 3SH and 3SHA are present in negligible concentrations in the grape berry, juice, and must, suggesting that they are released from non-volatile precursors present in the grape. The exploration of the nature and biogenesis of these precursors to 3SH and 3SHA has proven important for the elucidation of polyfunctional thiol biogenesis during alcoholic fermentation. The development and validation of appropriate analytical techniques for the analysis of 3SH precursors in enological matrices have been extensive, and this review explores the analysis and discovery of these precursor compounds. The development of analytical methods to analyze 3SH precursors, from the selection of the analytical instrument, sample preparation, and methods for standardization, will first be discussed, before highlighting how these techniques have been used in the elucidation of the biogenesis of 3SH and 3SHA in grape wines. Lastly, the future of thiol precursor analysis will be considered, with the development of new methods that greatly reduce the sample preparation time and enable multiple precursors, and the thiols themselves, to be quantitated using a single method.

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“…It has been suggested that H 2 S could be one of the sulfur donor (Harsch, Benkwitz, Frost, Colonna-Ceccaldi, Gardner, & Salmon, 2013). Then, sulfonic acids were hypothesized on structural basis but not identified yet (Duhamel, Piano, Davidson, Larcher, Fedrizzi, & Barker, 2015). Finally, cysteinyl-glycine S-conjugates to 4MMP (CysGly-4MMP) and γ-glutamyl-cysteine S-conjugate to 4MMP (γGluCys-4MMP) were not identified yet.…”

Section: Precursors and Mechanisms Of Transformationmentioning

confidence: 99%

Spotlight on release mechanisms of volatile thiols in beverages

et al. 2021

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Volatile thiols are very strong-smelling molecules that can impact the aroma of numerous foods, such as fruit and beverages. Several thiols and thiol precursors have already been reported in different plants used as raw material for beverage production, either fermented or not. We focus on those thiols in beverages and their release mechanisms from precursors during the different biotechnological steps of their processes. Volatile thiols in food can be classified in two different groups: low-molecular-weight volatile thiols, which impact the smell negatively, and volatile thiols with higher boiling points, which contribute positively to the aroma profile. The first part is devoted to volatile thiols without taking into account the highly malodorous small molecules as H 2 S, methanethiol, etc. The second part deals with precursors and the different release mechanisms induced by various processes such as extraction, roasting or fermentation, and the culture method that can influence the amount of thiol and their precursors.

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Synthesis of alkyl sulfonic acid aldehydes and alcohols, putative precursors to important wine aroma thiols

Cited by 16 publications

References 27 publications

Spotlight on Varietal Thiols and Precursors in Grapes and Wines

Spotlight on Varietal Thiols and Precursors in Grapes and Wines

Unraveling the Mystery of 3-Sulfanylhexan-1-ol: The Evolution of Methodology for the Analysis of Precursors to 3-Sulfanylhexan-1-ol in Wine

Spotlight on release mechanisms of volatile thiols in beverages

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