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{{Chembox |
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|Watchedfields = changed |
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| verifiedrevid = 452176692 |
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|verifiedrevid = 456502836 |
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| ImageFile =4-Hydroxy-TEMPO.svg |
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|ImageFile = 4-Hydroxy-TEMPO.svg |
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| ImageSize = |
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|ImageSize = 175 |
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| ImageAlt = |
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|ImageAlt = Skeletal formula of 4-hydroxy-TEMPO |
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| IUPACName = 1-λ<sup>1</sup>-oxidanyl-2,2,6,6-tetramethylpiperidin-4-ol |
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|ImageFile1 = 4-Hydroxy-TEMPO radical ball.png |
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| OtherNames = tempol; tanol; TMPN; 4-Oxypiperidol; nitroxyl 2; HyTEMPO |
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|ImageSize1 = 175 |
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| Section1 = {{Chembox Identifiers |
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|ImageAlt1 = Ball-and-stick model of the 4-hydroxy-TEMPO molecule |
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| CASNo =2226-96-2 |
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|PIN = (4-Hydroxy-2,2,6,6-tetramethylpiperidin-1-yl)oxyl |
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| ChEMBL = 607023 |
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|OtherNames = tempol; tanol; TMPN; 4-Oxypiperidol; nitroxyl 2; HyTEMPO |
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| PubChem =137994 |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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|CASNo_Ref = {{cascite|correct|CAS}} |
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| ChemSpiderID = 121639 |
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|CASNo = 2226-96-2 |
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| SMILES = CC1(CC(CC(N1)(C)C)O)C |
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|UNII_Ref = {{fdacite|correct|FDA}} |
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| InChI = 1/C9H18NO2/c1-8(2)5-7(11)6-9(3,4)10(8)12/h7,11H,5-6H2,1-4H3 |
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|UNII = U78ZX2F65X |
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| InChIKey = UZFMOKQJFYMBGY-UHFFFAOYAG |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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|ChEMBL_Ref = {{ebicite|correct|EBI}} |
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|ChEMBL = 607023 |
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| StdInChI = 1S/C9H18NO2/c1-8(2)5-7(11)6-9(3,4)10(8)12/h7,11H,5-6H2,1-4H3 |
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|PubChem = 137994 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| StdInChIKey = UZFMOKQJFYMBGY-UHFFFAOYSA-N |
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|ChemSpiderID = 121639 |
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| SMILES = CC1(CC(CC(N1)(C)C)O)C}} |
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|ChEBI = 180664 |
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| Section2 = {{Chembox Properties |
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|SMILES = CC1(C)CC(O)CC(C)(C)N1 |
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| Formula =C<sub>9</sub>H<sub>18</sub>NO<sub>2</sub> |
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|InChI = 1S/C9H18NO2/c1-8(2)5-7(11)6-9(3,4)10(8)12/h7,11H,5-6H2,1-4H3 |
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| MolarMass =172.24 g/mol |
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|InChIKey = UZFMOKQJFYMBGY-UHFFFAOYSA-N |
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| Appearance = orange crystals |
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|StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| Density = |
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|StdInChI = 1S/C9H18NO2/c1-8(2)5-7(11)6-9(3,4)10(8)12/h7,11H,5-6H2,1-4H3 |
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| MeltingPt = |
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|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| BoilingPt = |
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|StdInChIKey = UZFMOKQJFYMBGY-UHFFFAOYSA-N |
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| Solubility = }} |
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}} |
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| Section3 = {{Chembox Hazards |
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|Section2={{Chembox Properties |
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| MainHazards = |
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|C=9|H=18|N=1|O=2 |
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| FlashPt = |
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|Appearance = Orange crystals |
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| Autoignition = }} |
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|MeltingPtC = 71–73 |
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|MeltingPt_ref = <ref>{{cite journal|last1=Zakrzewski|first1=Jerzy|last2=Krawczyk|first2=Maria|title=Reactions of Nitroxides. Part XII . – 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|journal=Zeitschrift für Naturforschung B|date=1 January 2011|volume=66|issue=5|pages=493–498 |doi=10.1515/znb-2011-0509|s2cid=51802316 |doi-access=free}}</ref> |
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|Solubility = 629.3 g/L (20 °C)}} |
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|Section3={{Chembox Hazards |
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|GHSPictograms = {{GHS07}}<ref name="sigma">{{Sigma-Aldrich|id=176141|name=4-Hydroxy-TEMPO|accessdate=2015-08-24}}</ref> |
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|GHSSignalWord = Warning<ref name="sigma" /> |
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|HPhrases = {{H-phrases|302|315|319|335}}<ref name="sigma" /> |
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|PPhrases = {{P-phrases|261|305+351+338}}<ref name="sigma" /> |
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'''4-Hydroxy-TEMPO''' or '''TEMPOL''', formally 4-hydroxy-2,2,6,6-tetramethylpiperidin-1-oxyl, is a heterocyclic compound. Like the related ], it is used as a catalyst, chemical oxidant. |
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==Biological effects== |
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This compound show radioprotective, life-prolonging properties in animal models suggesting its usefulness in human diseases treatment<ref name="Wilcox-2010">{{Cite journal | last1 = Wilcox | first1 = CS. | title = Effects of tempol and redox-cycling nitroxides in models of oxidative stress. | journal = Pharmacol Ther | volume = 126 | issue = 2 | pages = 119-45 | month = May | year = 2010 | doi = 10.1016/j.pharmthera.2010.01.003 | PMID = 20153367 }}</ref>. It has been studied in human subjects for radiation induced ] prevention.<ref name="Metz-2004">{{Cite journal | last1 = Metz | first1 = JM. | last2 = Smith | first2 = D. | last3 = Mick | first3 = R. | last4 = Lustig | first4 = R. | last5 = Mitchell | first5 = J. | last6 = Cherakuri | first6 = M. | last7 = Glatstein | first7 = E. | last8 = Hahn | first8 = SM. | title = A phase I study of topical Tempol for the prevention of alopecia induced by whole brain radiotherapy. | journal = Clin Cancer Res | volume = 10 | issue = 19 | pages = 6411-7 | month = Oct | year = 2004 | doi = 10.1158/1078-0432.CCR-04-0658 | PMID = 15475427 }}</ref> |
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'''4-Hydroxy-TEMPO''' or '''TEMPOL''', formally 4-hydroxy-2,2,6,6-tetramethylpiperidin-1-oxyl, is a ]. Like the related ], it is used as a ] and chemical ] by virtue of being a stable ]. Its major appeal over TEMPO is that it is less expensive, being produced from ], which is itself made via the condensation of ] and ]. This makes it economically viable on an industrial scale.<ref>{{cite journal|last1=Ciriminna|first1=Rosaria|last2=Pagliaro|first2=Mario|title=Industrial Oxidations with Organocatalyst TEMPO and Its Derivatives|journal=Organic Process Research & Development|date=15 January 2010|volume=14|issue=1|pages=245–251|doi=10.1021/op900059x}}</ref> |
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This nitroxide antioxidant is already undergoing prospective clinical studies for several conditions. On the contrary, it was found to '''stimulate''' calcifcation in aortic atherosclerosis model through generation of H<sub>2</sub>O<sub>2</sub>.<ref name="Liberman-2008">{{Cite journal | last1 = Liberman | first1 = M. | last2 = Bassi | first2 = E. | last3 = Martinatti | first3 = MK. | last4 = Lario | first4 = FC. | last5 = Wosniak | first5 = J. | last6 = Pomerantzeff | first6 = PM. | last7 = Laurindo | first7 = FR. | title = Oxidant generation predominates around calcifying foci and enhances progression of aortic valve calcification. | journal = Arterioscler Thromb Vasc Biol | volume = 28 | issue = 3 | pages = 463-70 | month = Mar | year = 2008 | doi = 10.1161/ATVBAHA.107.156745 | PMID = 18162610 }}</ref> |
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], which is itself made from acetone and ammonia]] |
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In biochemical research, 4-hydroxy-TEMPO has been investigated as an agent for limiting ]. It catalyzes the ] of ], facilitates ] metabolism, and inhibits ] chemistry.<ref>{{cite journal | doi = 10.1124/pr.108.000240 | title = Chemistry and Antihypertensive Effects of Tempol and Other Nitroxides | year = 2008 | last1 = Wilcox | first1 = C. S. | last2 = Pearlman | first2 = A. | journal = Pharmacological Reviews | volume = 60 | issue = 4 | pages = 418–69 | pmid = 19112152 | pmc = 2739999}}</ref> 4-Hydroxy-TEMPO, along with related ]s, are being studied for their potential antioxidant properties.<ref>{{cite journal | doi = 10.3390/ijms18112490 | title = Nitroxides as Antioxidants and Anticancer Drugs | year = 2017 | last1 = Lewandowski | first1 = M | last2 = Gwozdzinski | first2 = K. | journal = International Journal of Molecular Sciences | volume = 18 | issue = 11 | pages = 2490 | pmid = 29165366 | pmc = 5713456| doi-access = free }}</ref> |
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On an industrial-scale 4-hydroxy-TEMPO is often present as a structural element in ], which are commonly used stabilizers in plastics, it is also used as a ], particularly during the purification of styrene. |
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It is a promising model substance to inhibit SARS-CoV-2 RNA-dependent RNA polymerase.<ref>{{cite journal | doi = 10.1126/science.abi5224 | title = Fe-S cofactors in the SARS-CoV-2 RNA-dependent RNA polymerase are potential antiviral targets | year = 2021 | last1 = Maio| first1 = N. | last2 = Lafont| first2 = B.A.P. | last3 = Sil| first3 = D. | last4 = Li| first4 = Y. | last5 = Bollinger | first5 = M. | last6 = Krebs | first6 = C. | journal = Science | volume = 373 | issue = 6551 | pages = 236–241 | pmid = 34083449 | pmc = 8892629 | doi-access = free }}</ref> |
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==See also== |
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* ] |
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==References== |
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==References== |
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{{Reflist}} |
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{{Reflist}} |
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==External links== |
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* http://www.organic-chemistry.org/chemicals/oxidations/tempo-2,2,6,6-tetramethylpiperidinyloxy.shtm |
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{{DEFAULTSORT:Hydroxy-TEMPO, 4-}} |
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{{organic-compound-stub}} |
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