Preparation and thermal properties of Heyns compounds based on two different amino acids

This study synthesized two Heyns compounds: 2-L-tyrosine-2-deoxy-D-glucose (Glu-Tyr) and 2-L-aspartic acid-2-deoxy-D-glucose (Glu-Asp), through reactions of D-fructose with L-tyrosine or L-aspartic acid, respectively. Structural confirmation was achieved via Fourier transform infrared spectroscopy (FTIR), nuclear magnetic resonance (NMR), and high-resolution mass spectrometry (HRMS), with yields of 61.4% for Glu-Tyr and 78.2% for Glu-Asp.Thermogravimetric (TG) analysis revealed that Glu-Asp underwent thermal decomposition at a lower temperature than Glu-Tyr. Both compounds exhibited strongly linear thermal release kinetics under varying heating rates. pyrolysis gas chromatography/mass spectrometry (Py-GC/MS) analysis demonstrated distinct flavor profiles: Glu-Tyr primarily released floral phenolic esters, whereas Glu-Asp generated baking aroma substances at 350°C and Caramel aromatic substances at 900°C. Application assessments indicated that Glu-Asp showed potential for traditional cigarettes, while Glu-Tyr exhibited superior compatibility with heated tobacco products. Headspace solid-phase microextraction-GC/MS (HS-SPME-GC/MS) further revealed a time-dependent increase in both the diversity and concentration of volatile compounds during heating.These findings establish a theoretical framework for the targeted application of Heyns compounds in flavor engineering.