Phenolic Antioxidants: Redox Properties and Antioxidant Activities

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Phenolic compounds are known for their antioxidant properties, which is important in the biological setting [1]. The cellular damage induced by reactive oxygen species, ROS, or others leads to diseases. However, foods or drugs which contain phenolic moieties are viable antioxidants which reduce ROS and minimize cell damage. Hence, greater understanding of this class of compounds will lead to an ideal antioxidant with tailored properties for applications in biology, food safety, among others. The relationship between structure-properties-function was evaluated by using voltammetric methods. We have explored redox properties of phenol-based compounds, such as tert-butylhydroxyphenol and its analogues by using Cyclic Voltammetry (CV) as well as Square-Wave Voltammetry (SWV) in order to rank order such compounds based on their redox potentials and structural parameters [2]. We have discovered that under electrochemical conditions, rather than chemical ones, such compounds may undergo cross-coupling reactions leading to photochromic products. The reactivity of such phenolic analogues was also explored by CV in the study with reactive oxygen species, specifically, superoxide anion radical [3]. More recently, we have started exploring compounds with multiple hydroxyl groups, such as flavonoids. The research findings on a variety of hydroxyl-containing aromatics will be presented and described. 1. Ingold, K. U., Pratt, D. A. Advances in radical-trapping antioxidant chemistry in the 21st century: a kinetic and mechanisms perspective. Chem. Rev. 2014, 9022-9046.2. Zabik, N., Virca, C. N., McCormick, T., Martic-Milne, S. Selective electrochemical versus chemical oxidation of bulky phenols. J. Phys. Chem. B, 2016, 120, 8914–8924.3. Zabik, N., Anwar, S., Ziu, I., Martic-Milne, S., Electrochemical reactivity of bulky-phenols with superoxide anion radical. Electrochim. Acta, 2019, 296, 174-180