Octadecyl ferulate behavior in 1,2-Dioleoylphosphocholine liposomes

•Octadecyl ferulate (ODF) was synthesized using Supercritical Fluid Chromatography.•ODF has a melting transition at 67 °C.•ODF stabilized liposomes and maintained antioxidant capacity within a bilayer.•Atomic force microscopy depicted domain formation by ODF in a supported bilayer.•Experiments and modeling suggest that ODF resides deeper within the bilayer.

Octadecyl ferulate was prepared using solid acid catalyst, monitored using Supercritical Fluid Chromatography and purified to a 42% yield. Differential scanning calorimetry measurements determined octadecyl ferulate to have melting/solidification phase transitions at 67 and 39 °C, respectively. AFM imaging shows that 5-mol% present in a lipid bilayer induced domains to form. Phase behavior measurements confirmed that octadecyl ferulate increased transition temperature of phospholipids. Fluorescence measurements demonstrated that octadecyl ferulate stabilized liposomes against leakage, maintained antioxidant capacity within liposomes, and oriented such that the feruloyl moiety remained in the hydrophilic region of the bilayer. Molecular modeling calculation indicated that antioxidant activity was mostly influenced by interactions within the bilayer.

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