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…

Impact of sulfur compounds to the antioxidant stability of white wines

The chemical mechanisms involved in oxidation/reduction potential of wine during winemaking and aging are affecting its color, aroma and taste. Chemical oxidation is one of the major causes of development of off-flavors during ageing1. Thus, the chemical changes in wine during storage should be controlled to ensure the sensory quality of the product and avoid consumer rejection that will compromise the economic value of the product. The 1-hydroxyethyl radical has been recognized as the key radical intermediate in the oxidative reactions in wine2. Based on the kinetic study of POBN-1-hydroxyethyl spin adduct formation in wines initiated via the Fenton reaction, a novel tool was recently developed in our laboratory to quantify the resistance of wines against oxidation3.

Comparison of various storage conditions to preserve polyphenols in red-grape pomace

Red grape pomace, a waste from wine production, can be valorised by extracting polyphenols, high-added value compounds used in cosmetics or oenology. For use at an industrial level, using green extraction techniques, pomace need to be stored before being processed. The aim of this study is to test various storage conditions in order to maintain high level of polyphenols over 180 days, while keeping storage cost economically interesting. In a first step, different storage conditions (ambient temperature or cooled (4°C) temperature, anaerobic (saturation with N2) or aerobic conditions, and addition of sulphur dioxide (SO2)) were compared on small samples (1 kg) packed in plastic pockets. The quality of storage was assessed by following the optical density of the pomace extract at 280 nm (DO 280 expressed as mg/l eq gallic acid), which is an indication of the amount of remaining extractable polyphenols.

WineMetrics: A new approach to unveil the “wine-like aroma” chemical feature

“The Human being has an excellent ability to detect and discriminate odors but typically has great difficulty in identifying specific odorants”(1). Furthermore, “from a cognitive point of view the mechanism used to judge wines is closer to pattern recognition than descriptive analysis.” Therefore, when one wants to reveal the volatile “wine-like feature” pattern recognition techniques are required. Sensomics is one of the most recent “omics”, i.e. a holistic perspective of a complex system, which deals with the description of substances originated from microorganism metabolism that are “active” to human senses (2). Depicting the relevant volatile fraction in wines has been an ongoing task in recent decades to which several research groups have allocated important resources. The most common strategy has been the “target approach” in order to identify the “key odorants” for a given wine varietal.

Accumulation of polyphenols in Barbera and Nebbiolo leaves during the vegetative season

Grapevine berries produce thousands of secondary metabolites of diverse chemical nature that have been largely detailed in the past due to their importance for defining wine quality. The wide Vitis vinifera diversity, resulting in thousands of different varieties well detailed in many studies regarding berries, is still not investigated in vegetative organs, leaves in particular. Deepening knowledge related to this aspect could be of great interest for many reasons (for example the possibility of using leaf extract for pharmaceutical, cosmetic and nutrition purposes) but, above all, for understanding the susceptibility of different grapevine varieties to pathogens.

Phenolic profiles of minor red grape cultivars autochthonous from the Spanish region of La Mancha

The phenolic profiles of little known red grape cultivars, namely Garnacho, Moribel and Tinto Fragoso, which are autochthonous from the Spanish region of La Mancha (ca. 600,000 ha of vineyards) have been studied over the consecutive seasons of years 2013 and 2014. The study was separately performed over the skins, the pulp and the seeds, and comprised the following phenolic types: anthocyanins, flavonols, hydroxycinnamic acid derivatives (HCADs), total proanthocyanidins (PAs) and their structural features. The selected grape cultivars belong to the Vine Germplasm Bank created in this region in order to preserve the great diversity of genotypes grown in La Mancha.