A series of novel lipid functionalized poly(epsilon-caprolactone)s (PCLs) were synthesized through ROP of epsilon-caprolactone in the presence of threo-9,10-dihydroxyoctadecanoic acid, synthesized from oleic acid. PCLs with different molecular weights were obtained by controlling the molar ratio of the initiator to the monomer. DSC and XRD analysis indicate that the crystallinity of PCLs decreased when compared to unfunctionalized PCL. The enzymatic degradation study shows that for samples with lower lipid derivatives content, a higher enzymatic degradation rate was observed because the lipase enzymes attack the ester bonds of the polymer; increased lipid content therefore inhibits the action of the lipase enzymes. (C) 2010 Wiley Periodicals, Inc. J Appl Polym Sci 119: 1848-1856, 2011