Macrowine 2021
IVES 9 IVES Conference Series 9 Reaction Mechanisms of Copper and Iron with Hydrogen Sulfide and Thiols in Model Wine

Reaction Mechanisms of Copper and Iron with Hydrogen Sulfide and Thiols in Model Wine

Abstract

Fermentation derived sulfidic off-odors due to hydrogen sulfide (H2S) and low molecular weight thiols are commonly encountered in wine production and removed by Cu(II) fining. However, the mechanism underlying Cu(II) fining remains poorly understood, and generally results in increased Cu concentration that lead to deleterious reactions in finished wine. The present study describes a mechanistic investigation of the iron and copper mediated reaction of H2S, cysteine, 3-sulfanylhexan-1-ol, and 6-sulfanylhexan-1-ol with oxygen. The concentrations of H2S, thiols, oxygen, and acetaldehyde were monitored over time. It was found that Cu(II) was rapidly reduced by both H2S and thiols to Cu(I). The addition of Fe(III) in combination with Cu resulted in the rapid reduction of Fe(III) by Cu(I) and the resulting Fe(II) redox cycled by reacting with oxygen. Furthermore, the presence of Fe and thiols prevented the removal of H2S by precipitation as insoluble CuS promoting H2S oxidation and formation of polysulfides, effectively keeping both metals and sulfide species in wine after the copper fining process.

Publication date: May 17, 2024

Issue: Macrowine 2016

Type: Article

Authors

Gal Kreitman*, David Jeffery, John Danilewicz, Ryan Elias

*Penn State University

Contact the author

Tags

IVES Conference Series | Macrowine | Macrowine 2016

Citation

Related articles…

Development and validation of a standardized oxidation assay for the accurate measurement of the ability of different wines to form “de novo” oxidation-related aldehydes

From the standpoint of wine aroma oxidation there are two effects observed: aroma degradation of oxygen sensitive compounds (polyfunctional mercaptans) and the appearance of new substances with high aromatic power (acetaldehyde, methional, phenylacetaldehyde, sotolon, alkenals, isobutanal and 2, 3-metylbutanals) (1-5). According to our experience, Strecker aldehydes are compounds with highest sensory relevance in the oxidative degradation of many wines (5-7).

Grape metabolites, aroma precursors and the complexities of wine flavour

A critical aspect of wine quality from a consumer perspective is the overall impression of wine flavour, which is formed by the interplay of volatile aroma compounds, their precursors, and taste and matrix components. Grapes contribute some potent aroma compounds, together with a large pool of non-volatile precursors (e.g. glycoconjugates and amino acid conjugates). Aroma precursors can break down through chemical hydrolysis reactions, or through the action of yeast or enzymes, significantly changing the aroma profile of a wine during winemaking and storage. In addition, glycoconjugates of monoterpenes, norisoprenoids and volatile phenols, together with sulfur-conjugates in wine, provide a reservoir of additional flavour through the in-mouth release of volatiles which may be perceived retro-nasally.

Using elicitors in different grape varieties. Effect over their phenolic composition

Phenolic compounds are very important in crop plants and have been the subject of a large number of studies. Three main reasons can be cited for optimizing the level of phenolic compounds in crop plants: their physiological role in plants, their technological significance for food processing, and their nutritional characteristics1 Indeed, an enormous diversity of phenolic antioxidants is found in fruits and vegetables, and their presence and roles can be affected or modified by several pre- and postharvest cultural practices and/or food processing technologies (Ruiz-García et al. 2012, Goldman et al. 1999, Tudela et al. 2002). In winegrapes, the technological importance of phenolic compounds, mainly flavonoids, is well-known.

New molecular evidence of wine yeast-bacteria interaction unraveled by untargeted metabolomic profiling

Bacterial malolactic fermentation (MLF) has a considerable impact on wine quality. The yeast strain used for primary fermentation can consistently stimulate (MLF+ phenotype) or inhibit (MLF- phenotype) malolactic bacteria and the MLF process as a function of numerous winemaking practices, but the molecular evidence behind still remains a mystery. In this study, such evidence was elucidated by the direct comparison of extracellular metabolic profiles of MLF+ and MLF- yeast phenotypes. Untargeted metabolomics combining ultrahigh-resolution FT-ICR-MS analysis, powerful machine learning methods and a comprehensive wine metabolite database, discovered around 800 putative biomarkers and 2500 unknown masses involved in phenotypic distinction.

Cytochrome P450 CYP71BE5 from grapevine (Vitis vinifera) catalyzes the formation of the spicy aroma compound, (-)-rotundone

(-)-Rotundone, an oxygenated sesquiterpene, is a potent odorant molecule with a characteristic spicy aroma existing in various plants including grapes1. It is considered as a significant compound notably in wines and grapes because of its low sensory threshold (16 ng L-1 in red wine, 8 ng L-1 in water) and aroma properties. (-)-Rotundone was first identified in red wine made from the grape cultivar Syrah (regionally called Shiraz) in Australia1, and then it was found in several grape varieties such as Duras, Grüner Veltliner, Schioppettino and Vespolina from Europe2, 3. Several environmental factors affecting the accumulation of (-)-Rotundone during the grape maturation, were reported such as ambient temperature4, soil properties and topography5, soil moisture from irrigation and light exposure in the bunch zone by leaf removal2.