FOOD SCIENCE ›› 2018, Vol. 39 ›› Issue (5): 99-105.doi: 10.7506/spkx1002-6630-201805016

• Basic Research • Previous Articles     Next Articles

Synthesis and Pyrolysis of 2-L-Aspartic Acid-2-Deoxy-D-Glucose

LU Changtong1, CHEN Zhifei1, MA Yuping1,*, HOU Pei2, FU Yufeng1, ZHENG Fengyang1, LI Chenggang1, SUN Zhitao1, GAO Mingqi1, ZHANG Zhan1   

  1. 1. Technology Center, China Tobacco Henan Industrial Co. Ltd., Zhengzhou 450000, China; 2. School of Food and Biological Engineering, Zhengzhou University of Light Industry, Zhengzhou 450002, China
  • Online:2018-03-15 Published:2018-03-14

Abstract: 2-L-Aspartic acid-2-deoxy-D-glucose was synthesized from D-fructose and L-aspartic acid monopotassium salt, and it was characterized by Fourier transform infrared spectroscopy, 1H nuclear magnetic resonance (NMR), 13C NMR and high resolution mass spectroscopy. The thermogravimetric behavior, thermal pyrolysis behavior and antioxidant activity of 2-L-aspartic acid-2-deoxy-D-glucose was investigated using thermo gravimetry-derivative thermo gravimetry (TG-DTG), on-line pyrolysis-gas chromatography-mass spectrometry (Py-GC-MS), and 1-diphenyl-2-picrylhydrazyl (DPPH) scavenging and reducing capacity assays, respectively. The results showed that the synthetic product was confirmed to be the target compound. The target compound has a pyrolysis temperature of 187.8 ℃ and a total weight loss of 91.26% at 700 ℃. The number of pyrolysis products from the compound increased with reaction temperature. The pyrolysis products included heterocyclic hydrocarbons, ketones, carboxylic acids, aldehydes, phenols, olefins, alcohols and aromatic hydrocarbons and other compounds, which had baking, sweet aroma, burnt-sweet, cocoa-like incense, floral and milky aroma notes. The synthetic product possessed strong DPPH free radical scavenging and reducing capacity and could be regarded as a potential antioxidant.

Key words: 2-L-aspartic acid-2-deoxy-D-glucose, Heyns rearrangement reaction, synthesis, thermal weight loss, pyrolysis, gas chromatography-mass spectrometry, aroma notes

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