Phytosterols and their derivatives have attracted much attention because of their health benefits to
humans and are widely used in food, pharmaceuticals, and cosmetics in the past decades. While most
of the research has focused on free phytosterols and phytosteryl esters of fatty acids, few researches
reported on phytosteryl phenolates, the esters of phytosterols with phenolic acids. Two novel group phytosteryl
phenolates, namely phytosteryl sinapates and vanillates, were successfully chemoenzymatically
synthesised in this work and their structures confirmed. Fourier transform infrared (FTIR) and high performance
chromatography-mass spectrometry/mass spectrometry (HPLC–MS/MS) using atmospheric
pressure chemical ionisation (APCI) under both positive and negative ion modes were employed for this
purpose. High antioxidant capacity of phytosteryl sinapates was observed using both oxygen radical
absorbance capacity (ORAC) assay and cooked ground meat model system. Although phytosteryl vanillates
showed lower antioxidant capacity than phytosteryl sinapates, they were stronger antioxidants
than vanillic acid and vinyl vanillate in both assays employed. Conjugation of phytosterols with sinapic
or vanillic acid rendered higher antioxidant capacity. Further studies on health benefits of phytosteryl
sinapates and vanillates are necessary.