Theoretical Investigation for Exploring the Antioxidant Potential of Chlorogenic Acid: A Density Functional Theory Study

The main objective of this research was to conduct a theoretical investigation into the antioxidant properties of chlorogenic acid. Calculations based on the density functional theory were performed using the B3LYP exchange-correlation functional and the 6-311G standard basis set to determine the theoretical parameters, such as bond dissociation enthalpy and spin density. H atom abstraction from -OH groups was the most representative reaction pathway chosen for this study. From these calculations, it was estimated that bond dissociation enthalpies of hydroxyl groups were in the order of 3'-OH > 4'-OH > 2-OH > 1-OH. Spin densities of O-atoms of free radicals formed (after the removal of H atoms) from the hydroxyl groups of aromatic rings were lower than that of hydroxyl groups of alicyclic rings. On the basis of the calculated results, H atom abstraction from -OH groups of aromatic ring should be the main mechanism for the antioxidant potential of chlorogenic acid. Moreover, a comparison of bond dissociation enthalpy values for different phenolic acid antioxidants showed that the chlorogenic acid is a potent antioxidant. This theoretical investigation might be helpful for the future applications of chlorogenic acid in the field of the pharmacy and food industries.