Possible mechanism for involvement of cysteine in aroma production in wine

J Agric Food Chem. 2002 Oct 9;50(21):6160-4. doi: 10.1021/jf025604w.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cysteine / chemistry*
  • Gas Chromatography-Mass Spectrometry
  • Hydrogen-Ion Concentration
  • Magnetic Resonance Spectroscopy
  • Maillard Reaction
  • Mass Spectrometry
  • Odorants / analysis*
  • Pyruvaldehyde / chemistry
  • Wine / analysis*

Substances

  • Pyruvaldehyde
  • Cysteine