This work focuses on the process development of membrane-assisted solvent extraction of hydrophobic compounds such as monoterpenes. Beginning with the choice of suitable solvents, quantum chemical calculations with the simulation tool COSMO-RS were carried out to predict the partition coefficient (logP) of (S)-(+)-carvone and terpinen-4-ol in various solvent-water systems and validated afterwards with experimental data. COSMO-RS results show good prediction accuracy for nonpolar solvents like n-hexane, ethyl acetate and n-heptane even in the presence of salts and glycerol in aqueous medium. Based on the high logP value, n-heptane was chosen for the extraction of (S)-(+)-carvone in a lab-scale hollow-fiber membrane contactor. Two operation modes are investigated where experimental and theoretical mass transfer values, based on their related partition coefficients were compared. In addition, the process is evaluated in terms of extraction efficiency and overall product recovery, and its biotechnological application potential discussed. Our work demonstrates that the combination of in-silico prediction by COSMO-RS with membrane-assisted extraction is a promising approach for the recovery of hydrophobic compounds from aqueous solutions.