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A dual-target strategy was designed for the application of lignin nanoparticles in the lipase mediated biosynthesis of novel 3-<i>O</i>-ethyl-L-ascorbyl-6-ferulate and 3-<i>O</i>-ethyl-L-ascorbyl-6-palmitate and in their successive solvent-shift encapsulation in order to improve stability and antioxidant activity against temperature and pH-dependent degradation. The loaded lignin nanoparticles were fully characterized in terms of kinetic release, radical scavenging activity and stability under pH 3 and thermal stress (60 °C), showing improved antioxidant activity and high efficacy in the protection of ascorbic acid esters from degradation.