Meat flavor generation from different composition patterns of initial Maillard stage intermediates formed in heated cysteine-xylose-glycine reaction systems

Food Chem. 2019 Feb 15:274:79-88. doi: 10.1016/j.foodchem.2018.08.096. Epub 2018 Aug 23.

Abstract

Volatile compounds formed in model reactions involving synthesized initial Maillard intermediates Gly-Amadori and [13C5]-2-threityl-thiazolidine-4-carboxylic acids ([13C5]-TTCA) in different molar ratios and free cysteine and glycine were investigated by solid-phase microextraction/gas chromatography-mass spectrometry and gas chromatography-olfactometry. The 1:1 ratio composition pattern provided the highest yields of all the sulfur-containing compounds, the potent meaty flavors or their 13C-labeled/unlabeled fractions, indicating a moderate level of glycine relative to cysteine was optimum for maximally yielding meaty flavors in complex meat-like Maillard systems containing cysteine as well as glycine. In addition, the 1:1 ratio composition led to formation of 13C-labeled molecules of some key meaty flavors e.g. 2-furanthiol representing over 70%, indicating TTCA/glycine reaction was better than Gly-Amadori/cysteine to yield meaty flavors. Formation pathways of twenty-nine flavors were elucidated based on the detected isotope distribution patterns. In particular, 2-methyltetrahydrothiophen-3-one, 3-thiophenethiol, 2-ethylthiophene, 2,5-dimethylthiophene, and 5-methylthiophene-2-carboxaldehyde involved a new formation pathway. Thiophene-2-carboxaldehyde and 2-methylthieno[3,2-b]thiophene showed two formation pathways.

Keywords: (13)C-labeling; Amadori; Cysteine; Glycine; Maillard reaction; Meat flavor; Thiazolidine; Xylose.

MeSH terms

  • Aldehydes / analysis
  • Aldehydes / chemistry
  • Carbon Isotopes
  • Cysteine / chemistry*
  • Gas Chromatography-Mass Spectrometry
  • Glycine / chemistry*
  • Hot Temperature
  • Maillard Reaction*
  • Meat* / analysis
  • Solid Phase Microextraction
  • Sulfur Compounds / analysis
  • Taste*
  • Thiophenes / analysis
  • Thiophenes / chemistry
  • Volatile Organic Compounds / analysis
  • Volatile Organic Compounds / chemistry
  • Xylose / chemistry

Substances

  • Aldehydes
  • Carbon Isotopes
  • Sulfur Compounds
  • Thiophenes
  • Volatile Organic Compounds
  • Xylose
  • thiophene-2-carboxaldehyde
  • Cysteine
  • Glycine