A novel bio-based epoxy monomer with conjugated double bonds, glycidyl ester of eleostearic acid (GEEA) was synthesized from tung oil fatty acids and characterized by 1H-NMR and 13C-NMR. Differential scanning calorimeter analysis (DSC) and FT-IR were utilized to investigate the curing process of GEEA with dienophiles and anhydrides. DSC indicated that GEEA could crosslink with both dienophiles and anhydrides through Diels-Alder reaction and epoxy/anhydride ring-opening reaction. Furthermore, Diels-Alder crosslink was much more active than the ring-opening of epoxy and anhydride in the curing process. FT-IR also revealed that GEEA successively reacted with dienophiles and anhydrides in both crosslinking methods. Dynamic mechanical analysis (DMA) and mechanical tensile testing were used to study the thermal and mechanical properties of GEEA cured by maleic anhydride, nadic methyl anhydride and 1,1'-(methylenedi-4,1-phenylene)bismaleimide. Due to the independence between the curing agents, dienophile and anhydride, a series of thermosetting polymers with various properties could be obtained by adjusting the composition of these two curing agents.