Preparation and Characterization of 4‐Methoxy Cinnamoyl Glycerol

Abstract

Glycerol was reacted with 4-methoxy cinnamic acid to prepare the corresponding 4-methoxy cinnamoyl glycerol. The reaction proceeded in toluene under reflux conditions with p-toluenesulfonic acid catalyst. Reaction of equimolar amounts of reactants produced the monoester in 20% yield after 2 h. The product was isolated and characterized by FTIR, mass spectrometry, and NMR techniques. Results of mass spectrometry and NMR experiments showed that the ester linkage formed between the carboxylic acid and the primary hydroxyl of glycerol. The ester displayed strong absorbance between 250 and 350 nm and shows potential as a UV filter in formulations where hydrophilic compounds are advantageous.

Kinetics of enzymatic synthesis of monoferuloyl glycerol and diferuloyl glycerol by transesterification in [BMIM]PF6

“…Owning to the elevated temperatures, non-enantioselectivity, and pollution [12,14,15], chemical synthesis of FGs was limited. Compared with chemical methods, enzymatic synthesis of FGs showed many performances, such as, mild reaction conditions, high catalytic efficiency, high enantioselectivity, and low energy consumption [7,9,10].…”

1,3-Diferuloyl-sn-glycerol from the biocatalytic transesterification of ethyl 4-hydroxy-3-methoxy cinnamic acid (ethyl ferulate) and soybean oil

“…Ferulic acid and p-coumaric acid were esterified to glycerol via the Mitsunobu protocol (Batovska et al 2005). The esterification of ferulic acid and 4-methoxy-cinnamic acid to glycerol via condensation in refluxing toluene catalyzed by p-toluene sulfanoic acid was also reported (Holser 2008;Holser et al 2008). Sun et al (2007b) detailed an analytical scale, lipase-catalyzed synthesis of the same esterification but reported the need for a tenfold excess of glycerol to ferulic acid to obtain meaningful conversions.…”

Enzymatic synthesis of 4-methoxycinnamoylglycerol Uv filter mediated by immobilized-lipase and nanoparticle formation on N-succinylchitosan

“…The chemical characterization of both samples by FTIR after purification by liquid-liquid extraction in the presence of carbonate solution (Holser et al 2008) (Figure 3a) indicates the ester formation by the presence of carbonyl (-COOR) signals at 1700cm -1 , which is shift to 1740cm -1 due to the presence of the unsaturated and aromatic carbon conjugated system (Holser, 2008) and C-O stretches in the 1300-1000cm -1 . The band at 1688cm -1 , typical of -COOH group in the cinnamic acid (Patil et al 2011;Ferenc et al 2012), disappears in the sample synthesized by the enzymatic pathway.…”