The synthesis of a new-type antioxidant of feruloyl-oleylglycerol through lipase-catalyzed irreversible transesterification of vinyl ferulate (VF) and triolein (TO) was studied. Vinyl ferulate made the transesterification reaction irreversible. The structure of VF was identified by NMR and MS and the influential factors of substrate molar ratio, reaction time, reaction temperature, enzyme amount and water activity were systematically studied. Results indicated that in the toluene reaction system the optimal conditions are as follows: n(VF)∶n(TO)=1∶3, reaction time: 62 h, reaction temperature: 55℃, enzyme amount: 20 mg/mL and water activity(aw): 0.07. Under the optimal conditions, the maximum yield as high as 96.73% was obtained.