Recently, dietary oil with high diacylglycerol (DAG) contents, so called DAG-oil, was introduced in Japan and the USA. It was claimed that the oil mostly composed of DAG is metabolized differently from conventional triacylglycerol oil, reducing body weight and fat mass because DAG tends to be oxidized to provide energy rather than stored as fat in the body. Monoacylglcyerol and DAG could be prepared by lipase-catalyzed reactions including hydrolysis, esterification, and glycerolysis. In this study, modified lipid containing some DAG esterified with the health-beneficial medium-chain fatty acids and conjugated linoleic acid was produced by lipase-catalyzed reactions. Many health benefits of medium-chain fatty acids (C6:0-C12:0) and conjugated linoleic acid isomers have been reported, including anticarcinogenic and antiatherogenic activities, and being rapid energy sources for humans with little or no deposition as body fat. The produced lipid molecules in this study have potential applications as functional healthy dietary fats and oils.