Chemoenzymatic synthesis of feruloylated monoacyl- and diacyl-glycerols in ionic liquids.
Feruloylated monoacyl- and diacyl-glycerols (FMAGs and FDAGs) are lipophilic antioxidants and potential UV absorbers. FMAGs and FDAGs were synthesized by a novel chemoenzymatic method: firstly, ferulic acid was esterified with glycerol to synthesize glyceryl ferulate, using p-toluenesulfonic acid as chemical catalyst in 1-butyl-3-methylimidazolium tetrafluoroborate ([Bmim]BF(4)); secondly, glyceryl ferulate was esterified with oleic acid to synthesize FMAGs and FDAGs, using Novozym 435 as biocatalyst in 1-butyl-3-methylimidazolium hexafluorophosphate ([Bmim]PF(6)). The conversion of ferulic acid and yield of glyceryl ferulate in the first reaction were both 98%. The yields of FMAGs and FDAGs in the second reaction reached 34 +/- 2% and 66 +/- 3%, respectively.
Sun
Shangde
S
Lipid Technology and Engineering, School of Food Science and Engineering, Henan University of Technology, 140 Songshan South Road, 450052, Zhengzhou, Henan Province, Peoples Republic of China. sunshangde@hotmail.com
Yang
Guolong
G
Bi
Yanlan
Y
Xiao
Fugang
F
D000975:Antioxidants / Q000378:metabolism*; D001557:Benzenesulfonates / Q000378:metabolism; D003373:Coumaric Acids / Q000378:metabolism; D004800:Enzymes, Immobilized; D005656:Fungal Proteins; D007093:Imidazoles / Q000378:metabolism; D052578:Ionic Liquids / Q000378:metabolism*; D008049:Lipase / Q000378:metabolism; D050178:Monoglycerides / Q000378:metabolism*; D019301:Oleic Acid / Q000378:metabolism; D011837:Radiation-Protective Agents / Q000378:metabolism*
C412621:1-butyl-3-methylimidazolium hexafluorophosphate; C419324:1-butyl-3-methylimidazolium tetrafluoroborate; D000975:Antioxidants; D001557:Benzenesulfonates; D003373:Coumaric Acids; D004800:Enzymes, Immobilized; D005656:Fungal Proteins; D007093:Imidazoles; D052578:Ionic Liquids; D050178:Monoglycerides; D011837:Radiation-Protective Agents; C531553:glyceryl ferulate; D019301:Oleic Acid; C004999:ferulic acid; C093667:Novozyme 435; D008049:Lipase; C029501:4-toluenesulfonic acid