New experimental data on solid liquid equilibrium (SLE) phase diagrams for binary systems {(-)-menthol or thymol + n-dodecane, or 1-dodecanol, or 2-phenylethanol} are presented. An influence of chemical structure of both terpenoid and solvent on the solubility curves is established and discussed. The new data are addressed and compared to the SLE data with a different set of solvents published previously. Modeling of SLE in the investigated mixtures with three modern thermodynamic models, namely, modified UNIFAC (Dortmund), perturbed chain statistical associating fluid theory (PC-SAFT), and conductor-like screening model for real, solvents (COSMO-RS), is presented as well. The predictive capacity of the studied approaches is confronted and compared with respect to their physical foundations for representation of components forming the systems as well as relevant intermolecular interactions governing thermodynamic behavior of the mixtures.