This paper presents a series of structural modification of soybean oil (SBO). Transesterification of SBO with different alcohols produced SBO alkyl esters (alkyl: butyl, isobutyl, 2-ehtylhexyl). After reacting points were achieved with SBO alkyl esters epoxidation, hydroxyl esters were formed through ring opening esterification of epoxy groups with hexanoic acid and dodecyl acid without solvent and catalyst. Then, esterification of hydroxy groups on hydroxyl esters produced multiple esters. The hydroxyl esters and multiple esters products were evaluated on rheological behavior and oxidation stability through measurement of viscosity at 40 ºC and 100 ºC, pour point, oxidation onset temperature. Increasing the chain length of mid-chain esters improves viscosity and low temperature property, but decreases oxidation stability. Branching in the end-chain esters can improve viscosity and low temperature property. Esterification of hydroxy groups on hydroxyl esters can increase oxidation stability but decrease viscosity and low temperature property slightly.