Formation of styrene during the Maillard reaction is negligible

Abstract

The elucidation of chemical pathways and the identification of intermediates leading to vinylogous compounds such as acrylamide by the Maillard reaction have proven challenging. This study was conducted to assess the formation of styrene from L-phenylalanine, employing binary mixtures of the amino acid heated together with simple C₃-sugar analogue (1-hydroxyacetone) or methylglyoxal. The formation of the corresponding vinylogous product, i.e. styrene, was measured under different moisture, pH, and temperature conditions. The formation of intermediates over time was monitored by gas chromatography-mass spectrometry (GC-MS) and liquid chromatography-mass spectrometry (LC-MS) together with the target compound styrene. Two intermediates, i.e. 1-phenethylaminopropan-2-one and 2-phenylethylamine, play a role in the formation of styrene, the latter of more importance in high-moisture systems, whilst the former favours the release of styrene in low-moisture systems. The model further showed that Strecker-type reactions are of less importance in the formation of styrene, as the yield from single immediate precursors was maximally 0.03 mol%. The low conversion rate of L-phenylalanine to the vinylogous product and existing data on the occurrence of free L-phenylalanine in food plants suggests that the amounts of styrene expected in foods subjected to thermal treatment are negligible.

Keywords:

• Maillard reaction
• Amadori rearrangement product (ARP)
• L-phenylalanine
• 2-phenylethylamine
• phenylacetaldehyde
• styrene

Acknowledgements

The authors thank Mrs Francia Arce-Vera and Dr Thierry Delatour for conducting the NMR analyses and assisting in the interpretation of the NMR spectra; to Mrs Isabelle Tavazzi for the LC-HRMS analyses; and to Elisabeth Gouézec for GC-MS analysis of phenylethylamine and methylglyoxal.