Synthesis And Character Of Glycerol Methyl Fumarate

Multi-functional food additives have become an important orientation of developing the food additives.a,β-unsaturated carbonyl is an effective group of antimicrobial activity. Di-methyl fumarate is an effective preservative containing such group, but it is banned to used in food because of its skin allergy. In order to decrease its allergy, a new preservative was designed and synthesized and its antimicrobial, emulsion activities were studied.According to the principle of organic synthesis, a synthesis route called "one pot" was determined by using maleic anhydride as reactant. Based on single factor experiment result, the synthesis technology of glycerol methyl fumarate (GMF) optimized was as follow: Monomethyl maleate was synthesized by esterification of the same quantity maleic acid and methanol,when temperature ascended to 60℃, esterify time was 0.5h, and rate of milling was 600r/min. Glycerol methyl maleate was prepared by esterification of the same quantity maleic acid and glycerol, when temperature ascended to 85℃, esterify time was 3.5h, and with toluene-p-sulfonic acid as catalyst. Glycerol methyl maleate was prepared from Glycerol methyl maleate with SOCl2 as isomerization catalyst, the quantity of catalyst was 6 % of quantity of maleic acid, when temperature descended to 65℃,isomerization time was 2h . The productive rate of GMF was approximately 78%, and DE was 1.09.Production was white solid grain, range of melting point110-130℃,no-sublimation.The synthesis product was characterized by infra-red spectrometry and LC-MS.GMF of 1.09 DE had broad-spectrum inhibition activity to bacteria, yeast and mold, which did not change with the pH value of the medium. In the medium which pH value was 3～7, antimicrobial activity of GMF approached DMF. The changes of temperature which was from 27℃to 47℃will not have a significant effect on inhibitory of GMF. GMF had poor thermal stability and polymer would have occurred at high temperature, resulting in decreased inhibitory. Skin tests showed that GMF donot stimulate skin as DMF.GMF of 1.09 DE was non-ionic W/O surfactants, which HLB value was 9.1, pH values was about 7 and did not change with the concentration .CMC 0.6g/L and surface tension 43.3mN/m of 0.3% mass concentration.The emulsion activity of GMF was poor to Distilled Monoglyceride and Span-80,and CMC was lower than Distilled Monoglyceride and Span-80. The foam activity and stability of GMF was inferior to span-80 and Distilled Monoglyceride.Summarizing the anti-microbial activity and emulsion characters, GMF was a new, potential type of emulsified food preservative.