Enzymatic Synthesis, Characterization, Antioxidant Activity, and Density Functional Theory Calculation of Novel 1-O-alkylglyceryl Ferulate

To improve the lipophilicity and antioxidant potential of ferulic acid (FA), four novel 1- O -alkylglyceryl ferulates (C 8 Gly 1 F, C 12 Gly 1 F, C 16 Gly 1 F, and C 18:1 Gly 1 F) were synthesized via Novozym 435-catalyzed transesterification in n -hexane at 65 °C, achieving high conversion rates and good enzyme reusability. Crystallinity and thermal properties, analyzed by polarized light microscopy and DSC, revealed that C 12 Gly 1 F exhibited optimal crystallinity, while C 18:1 Gly 1 F, due to its unsaturated alkyl chain, was predominantly amorphous, suggesting enhanced solubility. Antioxidant assays (DPPH and ABTS) demonstrated higher radical scavenging activity compared to ethyl ferulate, with C 18:1 Gly 1 F showing the best performance. Density functional theory calculations revealed its high electron affinity, electrophilicity, and a delocalized HOMO–LUMO distribution, supporting its proposed antioxidant mechanism. These findings highlight the potential of 1- O -alkylglyceryl ferulates as effective lipophilic antioxidants for use in functional foods and lipid-based delivery systems.