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Three kinds of mycolic acids (MAs) (alpha-, keto and methoxy-MAs) extracted from several species of mycobacteria were used to prepare monolayer films on water, and the surface pressure-area (pi-A) isotherms of the monolayers have been compared, so that the monolayer characteristics of the MAs as in cell walls would be revealed, since the monolayer molecular aggregation is related to drug permeability via the molecular packing. It was expected that the limiting molecular areas of the isotherms would be changed only a little, which reflects the minor difference in chemical structure and conformation of the mycobacteria. Nevertheless, the results are largely different from the expectation, and two greatly different patterns of the limiting molecular area have been observed. In a new model for elucidation of the results, two parts in an MA molecule are separately considered, and both contributions to the molecular unfolding by the monolayer compression have been suggested. This model is found to be useful to totally understand the isotherm behaviors of MAs. The relationship between monolayer properties and chemical structures for MAs has been summarized for the first time.