Abstract One of the current challenges of the food industry is to develop lipid bases with the desired technological performance for food application and with lower caloric value, in compliance with new legislations. In this context, the objective of this research is to compare chemical and enzymatic interesterification as methods for obtaining structured low-calorie lipids. Both processes are of commercial importance, since they can be used to modify the physical characteristics of fat without generating trans fatty acids. The lipid matrices used were olive oil, soybean oil and fully hydrogenated crambe oil, behenic acid source, presenting anti-obesogenic potential. Samples interesterified were characterized regarding the physicochemical behavior and regiospecific distribution in comparison to the simple mixture of the raw materials, in order to show the importance of the interesterification process. There was a reduction in their solid fat content after interesterification, which improved their physical properties and there was an increase in consistency, while the simple mixture did not represented a good option for industrial use. There was a 47% increase of saturated fatty acids at the sn-1,3 position after enzymatic synthesis. The results indicate that the structured lipids obtained can be a viable alternative to replace fats in foods low calorie.