Przedstawiono badania aktywności przeciwutleniającej oraz lipofilowości octanu eugenylu (OE). Do identyfikacji OE zastosowano metody GC, FTIR/ATR, GC-MS oraz analizę widm 13C-NMR i 1H-NMR, a do oznaczeń aktywności antyoksydacyjnej wykorzystano metodę redukcji wolnego rodnika DPPH. W celu zbadania lipofilowości OE wyznaczono współczynnik podziału n-oktanol/woda (log P).
EN
Eugenol was esterified with AcOH in presence of (ClCO)₂ and pyridine (yield 100%, selectivity 100%). The ester was identified by mass IR and NMR spectroscopies and studied for antioxidant activity and lipophilicity. The antioxidant activity was detd. by the free 2,2-diphenyl-1-picrylhydrazyl radical redn. and increased from 25% up to 72% with in- creasing the ester concn. from 5 µg/mL up to 500 µg/mL. The octanol/water partition coeff. was a measure for the lipophilicity of the ester.
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In this review the current concepts of lipophilicity phenomenon are described. It especially deserves special attention in medicinal chemistry. Lipophilicity is the factor of crucial importance in biological action of chemical substances. It is the main physico-chemical determinant influencing the bioavailability, permeability and frequently the toxicity of drugs. Lipophilicity is thus one of the most important factors in research aimed at rational designing of new drugs, what is of great and still growing importance nowadays. In the present review the current definitions of lipophilicity and hydrophobicity are discussed. Next, the role of lipophilicity of drugs in living organisms is widely reviewed. The experimental methods of estimation of biological lipophilicity are described in their historical development. The most widely used method of measuring the lipophilicity of compounds is nowadays the liquid chromatography technique, especially in reversed phase mode (according to the definition of lipophilicity). RP-HPLC is a fast and very precise tool for determination of lipophilicity in a wide range of chemical compounds. In presented paper the influence of the chromatographic systems are described with special attention on novel stationary phases which closely mimic the biological environment (e.g., Immobilized Artificial Membrane phase). Next, the procedures for the determination of chromatographic lipophilicity parameters for a set of derivatives in polycratic and gradient modes are described. The importance of different retention parameters and their usefulness in assessing lipophilicity are widely examined. Finally, a brief description of calculating methods of lipophilicity estimations is presented.
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