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.[3]
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.[6]
^Zakrzewski, Jerzy; Krawczyk, Maria (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. 66 (5): 493–498. doi:10.1515/znb-2011-0509. S2CID 51802316.
^Ciriminna, Rosaria; Pagliaro, Mario (15 January 2010). "Industrial Oxidations with Organocatalyst TEMPO and Its Derivatives". Organic Process Research & Development. 14 (1): 245–251. doi:10.1021/op900059x.
^Wilcox, C. S.; Pearlman, A. (2008). "Chemistry and Antihypertensive Effects of Tempol and Other Nitroxides". Pharmacological Reviews. 60 (4): 418–69. doi:10.1124/pr.108.000240. PMC2739999. PMID 19112152.
^Lewandowski, M; Gwozdzinski, K. (2017). "Nitroxides as Antioxidants and Anticancer Drugs". International Journal of Molecular Sciences. 18 (11): 2490. doi:10.3390/ijms18112490. PMC5713456. PMID 29165366.
^Maio, N.; Lafont, B.A.P.; Sil, D.; Li, Y.; Bollinger, M.; Krebs, C. (2021). "Fe-S cofactors in the SARS-CoV-2 RNA-dependent RNA polymerase are potential antiviral targets". Science. 373 (6551): 236–241. doi:10.1126/science.abi5224. PMC8892629. PMID 34083449.
January 01, 1970
hydroxy, tempo, tempol, formally, hydroxy, tetramethylpiperidin, oxyl, heterocyclic, compound, like, related, tempo, used, catalyst, chemical, oxidant, virtue, being, stable, aminoxyl, radical, major, appeal, over, tempo, that, less, expensive, being, produced. 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 3 4 Hydroxy TEMPO Names Preferred IUPAC name 4 Hydroxy 2 2 6 6 tetramethylpiperidin 1 yl oxyl Other names tempol tanol TMPN 4 Oxypiperidol nitroxyl 2 HyTEMPO Identifiers CAS Number 2226 96 2 Y 3D model JSmol Interactive image ChEBI CHEBI 180664 ChEMBL ChEMBL607023 Y ChemSpider 121639 Y ECHA InfoCard 100 017 056 PubChem CID 137994 UNII U78ZX2F65X Y CompTox Dashboard EPA DTXSID4041280 InChI InChI 1S C9H18NO2 c1 8 2 5 7 11 6 9 3 4 10 8 12 h7 11H 5 6H2 1 4H3 YKey UZFMOKQJFYMBGY UHFFFAOYSA N YInChI 1S C9H18NO2 c1 8 2 5 7 11 6 9 3 4 10 8 12 h7 11H 5 6H2 1 4H3Key UZFMOKQJFYMBGY UHFFFAOYSA N SMILES CC1 C CC O CC C C N1 O Properties Chemical formula C 9H 18N O 2 Molar mass 172 248 g mol 1 Appearance Orange crystals Melting point 71 73 C 160 163 F 344 346 K 1 Solubility in water 629 3 g L 20 C Hazards GHS labelling Pictograms 2 Signal word Warning 2 Hazard statements H302 H315 H319 H335 2 Precautionary statements P261 P305 P351 P338 2 Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Y verify what is Y N Infobox references Example synthesis of 4 Hydroxy TEMPO from phorone which is itself made from acetone and ammonia 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 4 Hydroxy TEMPO along with related nitroxides are being studied for their potential antioxidant properties 5 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 6 See also editpH neutral aqueous organic flow batteriesReferences edit Zakrzewski Jerzy Krawczyk Maria 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 fur Naturforschung B 66 5 493 498 doi 10 1515 znb 2011 0509 S2CID 51802316 a b c d Sigma Aldrich Co 4 Hydroxy TEMPO Retrieved on 2015 08 24 Ciriminna Rosaria Pagliaro Mario 15 January 2010 Industrial Oxidations with Organocatalyst TEMPO and Its Derivatives Organic Process Research amp Development 14 1 245 251 doi 10 1021 op900059x Wilcox C S Pearlman A 2008 Chemistry and Antihypertensive Effects of Tempol and Other Nitroxides Pharmacological Reviews 60 4 418 69 doi 10 1124 pr 108 000240 PMC 2739999 PMID 19112152 Lewandowski M Gwozdzinski K 2017 Nitroxides as Antioxidants and Anticancer Drugs International Journal of Molecular Sciences 18 11 2490 doi 10 3390 ijms18112490 PMC 5713456 PMID 29165366 Maio N Lafont B A P Sil D Li Y Bollinger M Krebs C 2021 Fe S cofactors in the SARS CoV 2 RNA dependent RNA polymerase are potential antiviral targets Science 373 6551 236 241 doi 10 1126 science abi5224 PMC 8892629 PMID 34083449 Retrieved from https en wikipedia org w index php title 4 Hydroxy TEMPO amp oldid 1170018867, wikipedia, wiki, book, books, library,
