For developing indigestible lipids, symmetric triacylglycerol (ST) and asymmetric triacylglycerol (AT) were produced by enzymatic interesterification using high oleic sunflower oil, palmitic ethyl ester, and stearic ethyl ester in a shaking water bath. Used enzymes were Lipozyme RMIM for ST and Lipozyme TLIM for AT. To remove ethyl ester from reactants, methanol fractionation (reactant : methanol=1:5, w/v, 25°C) and florisil separation (reactant : florisil=1:8, w/w) were applied. Acetone fractionation (reactant : acetone=1:9, w/v) was implemented to separate triacylglcerol (TAG) species into ST and AT. Fractions Ⅰ (before fractionation), Ⅱ (after fractionation, liquid phase) and Ⅲ (after fractionation, solid phase) were separated from ST, whereas fractions Ⅳ (after 1st fractionation, liquid phase) and Ⅴ (after 2nd fractionation, solid phase) were from AT. From sn-2 fatty acid composition analysis, the sum of palmitic acid (C16:0) and stearic acid (C18:0) was 4.9∼6.5 area% in ST (Ⅰ, Ⅱ, Ⅲ), and 41.9∼43.9 area% in AT (Ⅳ, Ⅴ). In vitro digestion was performed for 0, 15, 30, 60, and 120 minutes at 37°C in a shaking water bath. For the digestion results, hydrolysis of Ⅴ was only 40% compared to others (Ⅰ, Ⅱ, Ⅲ, Ⅳ) at 120 minutes due to its melting point (49°C). However, initially (15 minutes), hydrolysis (%) was as follows: Ⅴ<Ⅲ<Ⅳ<Ⅰ, Ⅱ. This order was similar with that of melting point, and a higher TAG content (two saturated fatty acids) was associated with a higher melting point. On the other hand, fractions Ⅲ and Ⅳ showed similar complete melting points (32.5°C, 31.8°C) and different slip melting points (31.3°C, 19.5°C). Even though Ⅳ has a lower TAG content composed of two saturated fatty acids than Ⅲ, it had a similar melting point.