Study On The Synthesis And Thermal Degradation Properties Of New Maillard Reaction Intermediates

The Maillard reaction is widely found in nature and plays a pivotal role in the production and storage of foods such as bread,meat and tobacco.It is one of the main sources of food aroma.Amadori rearrangement products(ARPs)are important intermediates of Maillard reaction,which can produce a large amount of aroma and melanoid by degradation,plays a key role in the improvement of food color and the production of flavor and the nutritional value.Therefore,the reaction has been widely concerned and studied since its discovery,and the regulation of its degradation products has always been a hotspot and a difficult point of research.This article explores two aspects of Amadori rearrangement products.Based on the ARPs of glucose(Glu)and phenylalanine(Phe),three compounds were synthesized from D-fructose and L-phenylalanine,which are:derivatives 1with both hydroxyl and carboxyl groups.Derivative 2 with only carboxyl protection and ARPs-Glu-Phe without group protection.The three compounds were then thermally degraded under different temperature and solvent conditions.The thermal degradation products of these three compounds were analyzed by UV-Vis absorption spectroscopy and gas chromatography-mass spectrometry(GC-MS).The thermal cracking products at 350? were qualitatively and semi-quantitatively analyzed.The aim was to investigate the effects of temperature,degradation solvent system and group protection on the degradation of Amadori rearrangement products.On this basis,using derivative 1 as a template,tyrosine-glucose ARPs derivatives(Tyr-ARP)?tryptophan-glucose ARPs derivatives(Try-ARP)?a proline-glucose ARPs derivative(Pro-ARP)and an alanine-glucose ARPs derivative(Ala-ARP)were synthesized by extending the amino acid moiety.Thermal behavior and thermal stability of derivative 1(Phenylalanine-glucose ARPs derivative Phe-ARP),derivative 2 and the above four derivatives by thermogravimetry(TG-DTG)and differential scanning calorimetry(DSC)were studied.The pyrolysis products of the six derivatives were qualitatively and semi-quantitatively analyzed by Py-GC/MS at 300,600 and 900?,respectively.The purpose is to investigate the thermal properties of Amadori derivatives and the types and relative amounts of their degradation products to determine whether these new Maillard reaction intermediates have the potential to become perfume precursor.The results shows that:1.it is obvious that solvent and degradation temperature have great influence on the thermal degradation process of ARPs,and it is an effective method to adjust the type and quantity of final products.2.By protecting the group of Amadori rearrangement products,the type and quantity of degradation products are obviously controlled.The heterocyclic compounds are mainly furan,and the types and contents of harmful substances such as fused aromatic hydrocarbons are reduced.3.The six synthesized new Maillard reaction intermediates have good thermal stability at room temperature and can be pyrolyzed during heating to produce a variety of aroma substances and perfume precursors.Based on Amadori compounds,six Amadori derivatives were synthesized.The synthesis method was simple and well yield,and the effects of temperature,solvent and group protection on its degradation were explored innovatively.It not only deepens the understanding of the pyrolysis pathway of ARPs,but also provides a new idea for the precise regulation of ARPs degradation products,and verifies the possibility that these new Maillard reaction intermediates have potential as latent fragrance,providing experiments support for the development of new fragrances.