Hydrophobic deep eutectic solvents (HDES) are emerging as sustainable and tunable alter natives to conventional organic solvents due to their low toxicity, environmental compat ibility, and adjustable physicochemical properties. This study investigated the influence of hydrogen-bond donor type on the structure, surface properties, antibacterial activity, and extraction performance of menthol-based HDES, assessing their potential for environmen tal remediation. Five HDES were synthesized using levulinic acid, acetic acid, lactic acid, oleic acid, and linalool as hydrogen-bond donors and characterized by nuclear magnetic resonance and infrared spectroscopy. Quantum-chemical calculations predicted donor re activity and hydrogen-bonding interactions. Surface properties, including interfacial ten sion, contact angles, drop volume, and surface energy components, were measured, and polarity was determined using a solvatochromic probe. Antibacterial activity was tested against Gram-positive and Gram-negative bacteria and Candida species. Extraction effi ciency of methylene blue and diclofenac from aqueous solutions was evaluated to assess pollutant removal. The HDES exhibited low interfacial tension and dispersive-dominated surface energy, confirming their hydrophobic nature. Polarity was tunable according to hydrogen-bond donor type, with menthol–linalool HDES showing the strongest antibac terial activity. Extraction efficiencies ranged from 65 to 84% for methylene blue and 7 to 52% for diclofenac, highlighting the importance of donor selection, polarity, and vis cosity. Greenness evaluation using BAGI and ComplexGAPI tools confirmed superior environmental performance of the synthesized HDES. Menthol-based HDES thus provide multifunctional properties, combining tunable polarity, bioactivity, and efficient pollutant extra ction. They represent a promising class of environmentally friendly solvents for water purification, analytical applications, and sustainable chemical processes. Highlights ● Menthol-based HDES were synthesized using five hydrogen bond donors. ● The HDES exhibited low interfacial tension and dispersive surface energy. ● Solvent polarity was tuned by selecting hydrogen bond donors (ENR ≈ 52–57 kcal/mol). ● Menthol–linalool HDES showed the strongest antibacterial activity. 1 3 V. Vorobyova et al. ● The HDES efficiently extracted methylene blue and diclofenac.
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