Antioxidant phenolic esters with potential anticancer activity: solution equilibria studied by Raman spectroscopy

The solution Raman pattern of a series of structurally related hydroxycinnamic and hydroxybenzoicesters (caffeates and gallates) with potential antioxidant/anticancer activity was studied, for different biologically significant concentrations. The spectra were assigned with the help of theoretical calculations in the light of previously reported experimental data for these compounds in the solid state. Evidence of the formation of dimeric entities in solution, via (C)···O···H(O) and/or (C)O···H(C) intermolecular hydrogen bonds, was obtained. The dimer‐to‐monomer equilibrium, which influences the antioxidant activity of this kind of systems, was monitored through Raman titration experiments. Copyright © 2008 John Wiley & Sons, Ltd. The Raman pattern in solution of a series of structurally related caffeates and gallates with potential anticancer activity was studied. Evidence of the formation of dimeric entities in solution, via (C)O···H(O) and/or (C)O···H(C) intermolecular hydrogen bonds, was obtained. The dimer‐to‐monomer equilibrium, which determines the antioxidant activity of this kind of systems, was monitored through Raman titration experiments.