ln compartmentalized systems, it is generally considered advantageous for antioxidants to exhibit surface activity. Surface-activity, hence hydrophobicity, allows the antioxidant to fuse with lipid-water interfaces and membranes and to be efficiently ta ken up by living cells. Thus, hydrophobie antioxidants are supposedly more internalized within cells than their hydrophilic counterparts. As such, they are thought to more effectively deal with the many reactive oxygen species (ROS) released into the cytosol. One reliable strategy to design a surface-active antioxidant is to incorporate positioned lipophilic groups by lipophilization. To date, a multitude of lipophilized antioxidants have been synthesized to obtain multifunctional compounds called "phenolipids". To have a global picture ofthe raie of the lipophilic moiety on antioxidant activity, we tested other lipophilic moieties consisting of diacylglycerols grafted onto rosmarinic acid. Accordingly, herein is described a chemo-enzymatic route to prepare these 1,2- diacylglycerol rosmarinate conjugates with various chain lengths These phenolipids so prepared were then finally assessed for their antioxidant activity in a ROS-overexpressing cell line of human dermal fibroblasts.