Acetylation and methylation semisynthesis of oleanolic acid (OA) isolated from Syzygium aromaticum L. yielded two compounds: 3-acetoxyoleanolic acid (3-AOA) and 3-acetoxy, 28-methylester oleanolic acid (3-A,28-MOA). Anti-inflammatory properties of these compounds were assessed using the serotonin and fresh egg albumin-induced inflammatory test models in male Wistar rats weighing 250-300 g. Furthermore, erythrocyte membrane-stabilizing property of these compounds was evaluated in the heat- and hypotonicity-induced in vitro hemolysis test models. The two semisynthetic compounds significantly (p < 0.05) inhibited albumin-induced inflammation better than OA and indomethacin from 1-5 h post administration. Both compounds were membrane stabilizing in heat-induced hemolysis test while only 3-AOA showed membrane-stabilizing effects in a hypotonic milieu. Semisynthesis of OA yielded two compounds which had better in vivo anti-inflammatory and in vitro membrane-stabilizing properties.