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4-Hydroxy-TEMPO

Heterocyclic compound bearing a stable aminoxyl radical

Heterocyclic compound bearing a stable aminoxyl radical

4-Hydroxy-TEMPO or TEMPOL, formally 4-hydroxy-2,2,6,6-tetramethylpiperidin-1-oxyl, is a heterocyclic compound. Like the related TEMPO, it is used as a catalyst and chemical oxidant by virtue of being a stable aminoxyl radical. Its major appeal over TEMPO is that it is less expensive, being produced from triacetone amine, which is itself made via the condensation of acetone and ammonia. This makes it economically viable on an industrial scale.

In biochemical research, 4-hydroxy-TEMPO has been investigated as an agent for limiting reactive oxygen species. It catalyzes the disproportionation of superoxide, facilitates hydrogen peroxide metabolism, and inhibits Fenton chemistry. 4-Hydroxy-TEMPO, along with related nitroxides, are being studied for their potential antioxidant properties.

On an industrial-scale 4-hydroxy-TEMPO is often present as a structural element in hindered amine light stabilizers, which are commonly used stabilizers in plastics, it is also used as a polymerisation inhibitor, particularly during the purification of styrene.

It is a promising model substance to inhibit SARS-CoV-2 RNA-dependent RNA polymerase.

References

References

  1. (1 January 2011). "Reactions of Nitroxides. Part XII [1]. – 2,2,6,6-Tetramethyl-1-oxyl- 4-piperidyl Chloroformate – A New Reactive Nitroxyl Radical. A One-pot Synthesis of 2,2,6,6-Tetramethyl-1-oxyl-4-piperidyl N,N-Dialkyl-carbamates". Zeitschrift für Naturforschung B.
  2. {{Sigma-Aldrich
  3. (15 January 2010). "Industrial Oxidations with Organocatalyst TEMPO and Its Derivatives". Organic Process Research & Development.
  4. (2008). "Chemistry and Antihypertensive Effects of Tempol and Other Nitroxides". Pharmacological Reviews.
  5. (2017). "Nitroxides as Antioxidants and Anticancer Drugs". International Journal of Molecular Sciences.
  6. (2021). "Fe-S cofactors in the SARS-CoV-2 RNA-dependent RNA polymerase are potential antiviral targets". Science.
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free-radicals amine-oxides piperidines
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