Possible Mechanism for Involvement of Cysteine in Aroma Production in Wine

Abstract

Under conditions close to those of wine, that is, low pH, aqueous medium, and low temperatures, this work describes N-(2-sulfanylethyl)-2-oxopropanamide (1), a new intermediate in the formation of 2-acetylthiazole from methylglyoxal and cysteine. 1 was characterized by MS, derivatization MS, and (1)H and (13)C NMR and was synthesized from 2-sulfanylethanamine and ethyl pyruvate. A formation pathway for 2-acetylthiazole from methylglyoxal and cysteine is proposed, in which 1 is a new intermediate in Maillard-type reactions in systems under mild conditions.

Oxidation mechanisms occurring in wines

“…Although the Maillard reaction has been found in beer and other foods, there is little supportive evidence for its occurrence in wine browning (Main, 1992;Zoecklein et al, 1995). However, because wine contains the necessary Maillard reaction substrates such as amino acids, proteins, and reducing sugars, the possibility of its occurrence should not be overlooked (Zoecklein et al, 1995 volatile compounds responsible for typical aroma or aging aromas of some sweet natural wines seem to be linked with chemical like Maillard reactions between sugars and amino acids (Marchand, De Revel, & Bertrand, 2002;Potman & Van Wijk, 1989;Vernin, 1982).…”

Quantification of 3-deoxyglucosone (3DG) as an aging marker in natural and forced aged wines

“…Recent studies reported a number of volatile compounds with different aromas (sulphury, floral, toasted or roasted notes) in wine-model systems, presumably derived from Maillard-like reactions between -dicarbonyl compounds and amino acids (Kroh, 5 1994;Pripis-Nicolau, de Revel, Bertrand, & Maujean, 2000;Marchand, de Revel, Vercauteren, & Bertrand, 2002;de Revel, Marchand & Bertrand, 2003;Cerny & GuntzDubini, 2008;Marchand, Almy, & de Revel, 2011). Moreover, the production of Amadori compounds in wines has already been described by Hashiba 1978, and more recently several Maillard-like compounds have been identified in typical and ageing aromas of champagne wines (thiazoles and oxazoles like: 2,4-dimethylthiazole, 4-methylthiazole, 2-acetylthiazole, 2-acetyl-2-thiazoline, or 2,4,5-trimethyloxazole; and furanthiols like furan-2-yl-methanethiol) (Keim, de Revel, Marchand, & Bertrand, 2002;Tominaga, Guimbertau, & Dubourdieu, 2003) Formation of 3DG has been evaluated in model systems (Usui et al, 2007;Fiedler & Kroh, 2007;Golon & Kuhnert, 2013), biological samples (Hoffman, Kappler, Passmore, & Mehta, 2003;Hurtado-Sanchez, Espinosa-Mansilla, Rodrıguez-Caceres, Martın-Tornero & Durán-Merás, 2012), and food products such as: sake (Oka, 1969), soy sauce (Hashiba, 1976;Kim & Lee, 2008), balsamic vinegars (Daglia, Amoroso, Rossi, Mascherpa, & Maga, 2013), carbonated soft drinks (Gensberger, Glomb, & Pischetsrieder, 2013), milk products (Hellwig, Degen, & Henle, 2010), high-fructose corn syrups (Lo et al, 2008;Gensberger, Mittelmaier, Glomb, & Pischetsrieder, 2012;RuizMatute, Vazquez, Hernández-Hernández, Sanza, & Martínez-Castro, 2015), beers (Bravo et al, 2008;Hellwig, Nobis, Witte, & Henle, 2016), commercial honey samples (Weigel, Opitz, & Henle, 2004;Mavric, Wittmann, Barth, & Henle, 2008...…”

The Cysteine Reaction with Diacetyl under Wine‐Like Conditions: Proposed Mechanisms for Mixed Origins of 2‐Methylthiazole, 2‐Methyl‐3‐thiazoline, 2‐Methylthiazolidine, and 2,4,5‐Trimethyloxazole

“…Only one pathway of thiazoles generation under wine‐like conditions has been studied. It concerns 2‐acetylthiazole (Marchand and others 2002). Among the more prominent products are thiazoles, thiazolines, thiazolidines, and oxazoles having methyl groups at the 2‐position.…”