4-Hydroxy-TEMPO or TEMPOL, formally 4-hydroxy-2,2,6,6-tetramethylpiperidin-1-oxyl, is a

heterocyclic compound A heterocyclic compound or ring structure is a cyclic compound that has atoms of at least two different elements as members of its ring(s). Heterocyclic chemistry is the branch of organic chemistry dealing with the synthesis, properties, and ...

. Like the related

TEMPO In musical terminology, tempo (Italian, 'time'; plural ''tempos'', or ''tempi'' from the Italian plural) is the speed or pace of a given piece. In classical music, tempo is typically indicated with an instruction at the start of a piece (often ...

, it is used as a

catalyst Catalysis () is the process of increasing the rate of a chemical reaction by adding a substance known as a catalyst (). Catalysts are not consumed in the reaction and remain unchanged after it. If the reaction is rapid and the catalyst recyc ...

and chemical

oxidant An oxidizing agent (also known as an oxidant, oxidizer, electron recipient, or electron acceptor) is a substance in a redox chemical reaction that gains or " accepts"/"receives" an electron from a (called the , , or ). In other words, an oxid ...

by virtue of being a stable

aminoxyl radical Aminoxyl denotes a Radical (chemistry), radical functional group with general structure R2N–O•. It is commonly known as a nitroxyl radical or a nitroxide, however IUPAC discourages the use of these terms, as they erroneously suggest the presenc ...

. Its major appeal over TEMPO is that is less expensive, being produced from triacetone amine, which is itself made via the condensation of

acetone Acetone (2-propanone or dimethyl ketone), is an organic compound with the formula . It is the simplest and smallest ketone (). It is a colorless, highly volatile and flammable liquid with a characteristic pungent odour. Acetone is miscib ...

and

ammonia Ammonia is an inorganic compound of nitrogen and hydrogen with the formula . A stable binary hydride, and the simplest pnictogen hydride, ammonia is a colourless gas with a distinct pungent smell. Biologically, it is a common nitrogenous was ...

. This makes it economically viable on an industrial scale. 4-Hydroxy-TEMPO synthesis01

In biochemical research, 4-hydroxy-TEMPO has been investigated as an agent for limiting

reactive oxygen species In chemistry, reactive oxygen species (ROS) are highly reactive chemicals formed from diatomic oxygen (). Examples of ROS include peroxides, superoxide, hydroxyl radical, singlet oxygen, and alpha-oxygen. The reduction of molecular oxygen () p ...

. It catalyzes the

disproportionation In chemistry, disproportionation, sometimes called dismutation, is a redox reaction in which one compound of intermediate oxidation state converts to two compounds, one of higher and one of lower oxidation states. More generally, the term can b ...

superoxide In chemistry, a superoxide is a compound that contains the superoxide ion, which has the chemical formula . The systematic name of the anion is dioxide(1−). The reactive oxygen ion superoxide is particularly important as the product of the ...

, facilitates

hydrogen peroxide Hydrogen peroxide is a chemical compound with the formula . In its pure form, it is a very pale blue liquid that is slightly more viscous than water. It is used as an oxidizer, bleaching agent, and antiseptic, usually as a dilute solution (3%� ...

metabolism, and inhibits Fenton chemistry. 4-Hydroxy-TEMPO, along with related

nitroxide Aminoxyl denotes a radical functional group with general structure R2N–O•. It is commonly known as a nitroxyl radical or a nitroxide, however IUPAC discourages the use of these terms, as they erroneously suggest the presence of a nitro group. ...

s, 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 Hindered amine light stabilizers (HALS) are chemical compounds containing an amine functional group that are used as stabilizers in plastics and polymers. These compounds are typically derivatives of tetramethylpiperidine and are primarily used t ...

, which are commonly used stabilizers in plastics, it is also used as a

polymerisation inhibitor Polymerisation inhibitors (US: polymerization inhibitors) are chemical compounds added to monomers to prevent their auto-polymerisation. Unsaturated monomers such as acrylates, vinyl chloride, butadiene and styrene require inhibitors for both proces ...

, particularly during the purification of styrene. It is a promising model substance to inhibit SARS-CoV-2 RNA-dependent RNA polymerase.

References

{{DEFAULTSORT:Hydroxy-TEMPO, 4- Free radicals Amine oxides Piperidines

See also

References