Hydrocarbon autoxidation continues to challenge the development of petroleum derived products with increased longevity and high performance standards. Perhaps the most important strategy in slowing this process is via the addition of radical-trapping chain-breaking antioxidants to virtually all petroleum-derived materials, from lubricating oils and polymers, to rubbers, jet fuels and hydraulic fluids. In recent years, our group has designed and developed a new class of radical-trapping antioxidant with unprecedented activities. These so-called pyridinols and pyrimidinols, essentially heterocyclic analogs of phenols, will be introduced in the context of our efforts to use them as tools to unequivocally assess the importance of oxidative damage in vivo, from which their potential as additives to petroleum-derived products will be obvious. Furthermore, we will describe the design, synthesis and study of related aromatic amine compounds which are currently in development for various industrial applications. Finally, we will relay our efforts to unravel the fascinating radical chemistry of the key organosulfur compounds found in garlic and related plants. Our work provides unique insight into the reactivity of sulfenic acids, which have recently been identified as key participants in redox-mediated cell signaling events.

Recent advances in the chemistry of phenol, amine, and organosulfur radical-trapping antioxidants

243rd National Meeting (2012)

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