Theoretical design of new very potent free radical scavengers

The importance of radical scavengers in health or as preservatives in various media is well-established. Their properties are dependant of different factors such as their ability to donate a hydrogen atom or an electron, but also their lipophilicity and chain length for the protection of membranes. This paper presents new compounds with very potent radical scavenging potencies. The improvement in the magnitude of the quantities which reflect the radical scavenging ability can reach 10 kcal/mol with respect to vitamins C or E or other good radical scavengers such as flavonoids. The lipophilicity of these compounds can be increased by adding a tail at the good position without modifying their ability of donating a hydrogen atom. In the same way, the effect of addition of a sugar which increases the solubility in water is analysed.

Graphical abstractDownload full-size imageHighlights► Design of polyphenols with high Mulliken charges on hydroxyl group oxygen atoms. ► Calculation of the corresponding BDE. ► BDE lower than 10 kcal/mol with respect to the best known antioxidants. ► Study of the effect of addition of a lipophilic chain on antioxidant properties.