The mole fraction solubility data of trans-4-hydroxy-L-proline in 16 neat solvents (water, methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, sec-butanol, n-pentanol, acetone, 2-butanone, acetonitrile, dichloromethane, methyl acetate, ethyl acetate, and 1,4-dioxane) and a binary solvent mixture of water + acetonitrile were determined by the static gravimetric method from 283.15 to 333.15 K. In both neat and binary solvent systems, the solubility values increased with the increase of temperature. Analysis of the data showed that the solubility behavior was influenced by the polarity, hydrogen bond, cohesive energy density, and molecular structures. Six thermodynamic models, including the modified Apelblat, Yaws, Jouyban-Acree, Machatha, Apelblat-Jouyban-Acree, and Apelblat-Machatha models, were employed for fitting the solubility data. In addition, these models were assessed for classification by the Akaike information criterion values and Akaike weights.