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Natural monophenols exhibit various properties including antioxidant, therapeutic action and toxicity. This review is unique in application of a unifying mechanistic theme comprising electron transfer, reactive oxygen species and oxidative stress. Representative phenols are as follows: salicylic acid, guaiacol, eugenol, (S)-tyrosine, vanillin, capsaicin, 6-gingerol, carvacrol, thymol, tocopherol, 5-hydroxytryptamine, psilocin, sesamol, estradiol, cannabinoids, etoposide, morphine and heroin, cresols, and other related phenols, such as platensimycin and polyphenols (vancomycin and tetarimycin A). This approach to mode of action may assist in improved drug design.