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Regenerable Radical-Trapping Tellurobistocopherol Antioxidants
- Poon, Jia-fei, Yan, Jiajie, Singh, Vijay P., Gates, Paul J., Engman, Lars
- Journal of organic chemistry 2016 v.81 no.24 pp. 12540-12544
- acetylcysteine, alpha-tocopherol, antioxidants, free radicals, peroxidation, phosphine, tellurium, thiols
- Tellurobistocopherols 9–11 were prepared by lithiation of the corresponding bromotocopherols, reaction with tellurium tetrachloride and reductive workup. Compounds 9–11 quenched linoleic-acid-derived peroxyl radicals much more efficiently than α-tocopherol in a chlorobenzene/water two-phase system. N-Acetylcysteine or tris(2-carboxylethyl)phosphine as co-antioxidants in the aqueous phase could regenerate the tellurobistocopherols and increase their inhibition times. Antioxidant 11 inhibited peroxidation for 7-fold longer than that recorded with α-tocopherol. Thiol consumption in the aqueous phase was monitored and found to be inversely related to the inhibition time.