Enzymatic alkylsuccinylation of tyrosol: Synthesis, characterization and property evaluation as a dual-functional antioxidant

This work reports a novel approach to generate a new group of tyrosol-based amphiphilic lipid alkylsuccinylated tyrosol by lipase-catalyzed succinylation of tyrosol with alkylsuccinic anhydrides of varying alkyl chain lengths, in high yields (80–95%). The structures of the compounds were confirmed by MS, FTIR & 1H NMR; and their properties were characterized by Temperature-Ramp FTIR, DSC & CMC measurements. The synthesized compounds integrate water-soluble phenylethanoid and hydrophobic alkyl into one molecule thus are endowed with dual functions: retaining the antioxidant property of tyrosol and entailing tyrosol with new surface-active property. The DPPH activity of tyrosol (13.77%) was significantly enhanced by 2-dodecen-1-ylsuccinylated tyrosol (16.01%). Compared to tyrosol-based emulsions (76.63%), the lipid oxidation is reduced to 21.57% and 42.32% in 2-octen-1-ylsuccinylated/2-dodecen-1-ylsuccinylated tyrosol emulsions, respectively. This work brings new members to the library of functional lipid excipients and open a novel and effective synthetic pathway for derivation of phenyl alcohols.