The enzymatic polymerization of 12-hydroxystearic acid (12-HSA) was carried out with Lipase $CA^{(R)}$ in benzene to produce poly(12-hydroxystearate) (PHS) with a low molecular weight. When this polymerization was continued for a long reaction time, the PHS once formed was depolymerized into a cyclic diester, 13,16-dihexyl-1,14-dioxacyclohexacosane-2,15-dione (12-HSAD). Similar polymerization and depolymerization were observed when 12-hydroxyoleic acid (12-HOA) was treated with Lipase $CA^{(R)}$, whereas only polymerization occurred when 12-hydroxydodecanoic acid (12-HDA) was treated in a similar manner. The preferential formation of cyclic diesters for 12-HSA was attributed to the structural requirements due to the bulky n-hexyl side groups stemming from the ring systems.