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<p>To improve the lipophilicity and antioxidant potential of ferulic acid (FA), four novel 1-<i>O</i>-alkylglyceryl ferulates (C<sub>8</sub>Gly<sub>1</sub>F, C<sub>12</sub>Gly<sub>1</sub>F, C<sub>16</sub>Gly<sub>1</sub>F, and C<sub>18:1</sub>Gly<sub>1</sub>F) were synthesized via Novozym 435-catalyzed transesterification in <i>n</i>-hexane at 65&#xa0;°C, achieving high conversion rates and good enzyme reusability. Crystallinity and thermal properties, analyzed by polarized light microscopy and DSC, revealed that C<sub>12</sub>Gly<sub>1</sub>F exhibited optimal crystallinity, while C<sub>18:1</sub>Gly<sub>1</sub>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<sub>18:1</sub>Gly<sub>1</sub>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-<i>O</i>-alkylglyceryl ferulates as effective lipophilic antioxidants for use in functional foods and lipid-based delivery systems.</p>

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

  • 期刊论文

  • 发表日期：

    2026年1月29日

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  • Xinyu Zhang,
  • Yijie Li,
  • Hong Lin,
  • Junbo He,
  • Jiangtao Feng,
  • Meng Cai

摘要

To improve the lipophilicity and antioxidant potential of ferulic acid (FA), four novel 1-O-alkylglyceryl ferulates (C8Gly1F, C12Gly1F, C16Gly1F, and C18:1Gly1F) 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 C12Gly1F exhibited optimal crystallinity, while C18:1Gly1F, 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 C18:1Gly1F 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.