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176141 Aldrich

4-Hydroxy-TEMPO

97%

Synonym: 4-Hydroxy-2,2,6,6-tetramethylpiperidine 1-oxyl, TEMPOL

  • CAS Number 2226-96-2

  • Empirical Formula (Hill Notation) C9H18NO2

  • Molecular Weight 172.24

  •  Beilstein Registry Number 1422990

  •  EC Number 218-760-9

  •  MDL number MFCD00006478

  •  PubChem Substance ID 24850555

  • Popular Documents:  FTIR (PDF)  

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Description

Application

A fluorous-tagged TEMPO derivative was prepared from the derived TEMPO propargylic ether and subsequent "click" reaction with a fluorous azide. This TEMPO derivative proved to be a highly effective catalyst in the oxidation of alcohols with bleach.1

Spin label for studying biological compounds and polymers.

Spin label reagent used in the chatacterization of antagonist and agonist binding sites of NK1 receptor. Also used to measure reactive oxygen generation in heart muscle by electron spin resonance spectroscopy. Cells that overexpress CYP2E1 can be protected from arachidonic acid toxicity damage by TEMPOL.

Packaging

1, 5, 25 g in glass bottle

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Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
Hazard Codes (Europe) 
Xn
Risk Statements (Europe) 
Safety Statements (Europe) 
26-36
WGK Germany 
1
RTECS 
TN8991000

Protocols & Articles

Peer-Reviewed Papers

References

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1. Synlett, 2767, (2006)

Characterization of non-peptide antagonist and peptide agonist binding sites of the NK1 receptor with fluorescent ligands. Turcatti, G. J. Biol. Chem. 272, 21167, (1997)

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Enhanced generation of reactive oxygen species in the limb skeletal muscles from a murine infarct model of heart failure. Tsutsui, H. Circulation 104, 134, (2001)

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Effects of ACE inhibition on left ventricular failure and oxidative stress in Dahl salt-sensitive rats. Tsutsui, H. J. Cardiovasc. Pharmacol. 37, 725, (2001)

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Spin trapping agents (Tempol and POBN) protect HepG2 cells overexpressing CYP2E1 against arachidonic acid toxicity. Perez, M. J., Cederbaum, A. I. Free Radic. Biol. Med. 30, 734, (2001)

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Med. Sci. Res. 21, 401, (1993)

J. Polym. Sci. B. Polym. Phys. 31, 1885, (1993)

Detection of free radicals in the blood of animals using extracorporeal circulation. Free Radical Res. Commun. 19, S171, (1993)

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Type 5 adenylyl cyclase increases oxidative stress by transcriptional regulation of manganese superoxide dismutase via the SIRT1/FoxO3a pathway. Lai L, Yan L, Gao S, et al. Circulation 127(16), 1692-701, (2013)

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Probing the antimalarial mechanism of artemisinin and OZ277 (arterolane) with nonperoxidic isosteres and nitroxyl radicals. Matthias A Fügi et al Antimicrob. Agents Chemother. 54, 1042-6, (2010)

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Reduction of reactive oxygen species ameliorates metabolism-secretion coupling in islets of diabetic GK rats by suppressing lactate overproduction. Sasaki M, Fujimoto S, Sato Y, et al. Diabetes 62(6), 1996-2003, (2013)

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Tetrahydrobiopterin deficiency induces gastroparesis in newborn mice. Welsh C, Enomoto M, Pan J, et al. Am. J. Physiol. Gastrointest. Liver Physiol. 305(1), G47-57, (2013)

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The SIRT1 activator SRT1720 reverses vascular endothelial dysfunction, excessive superoxide production, and inflammation with aging in mice. Gano LB, Donato AJ, Pasha HM, et al. Am. J. Physiol. Heart Circ. Physiol. 307(12), H1754-63, (2014)

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Cytokine and radical inhibition in septic intestinal barrier failure. Schulz K, Sommer O, Jargon D, et al. J. Surg. Res. 193(2), 831-40, (2015)

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Angiotensin II in paraventricular nucleus contributes to sympathoexcitation in renal ischemia-reperfusion injury by AT1 receptor and oxidative stress. Seifi B, Kadkhodaee M, Bakhshi E, et al. J. Surg. Res. 193(1), 361-7, (2015)

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Effect of the addition of two superoxide dismutase analogues (Tempo and Tempol) to alpaca semen extender for cryopreservation. Acosta AS, Vargas SE, Cuya MV, et al. Theriogenology 79(5), 842-6, (2013)

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Tempol moderately extends survival in a hSOD1(G93A) ALS rat model by inhibiting neuronal cell loss, oxidative damage and levels of non-native hSOD1(G93A) forms. Linares E, Seixas LV, dos Prazeres JN, et al. PLoS ONE 8(2), e55868, (2013)

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Tempol prevents cardiac oxidative damage and left ventricular dysfunction in the PPAR-α KO mouse. Guellich A, Damy T, Conti M, et al. Am. J. Physiol. Heart Circ. Physiol. 304(11), H1505-12, (2013)

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Nephroprotective effects of TVP1022, a non-MAO inhibitor S-isomer of rasagiline, in an experimental model of diabetic renal ischemic injury. Abu-Saleh N, Awad H, Khamaisi M, et al. Am. J. Physiol. Renal Physiol. 306(1), F24-33, (2014)

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Liquid state DNP of water at 9.2 T: an experimental access to saturation. Neugebauer P, Krummenacker JG, Denysenkov VP, et al. Phys. Chem. Chem. Phys. 15(16), 6049-56, (2013)

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Systemic DNA damage accumulation under in vivo tumor growth can be inhibited by the antioxidant Tempol. Georgakilas AG, Redon CE, Ferguson NF, et al. Cancer Lett. 353(2), 248-57, (2014)

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Placental oxidative stress and decreased global DNA methylation are corrected by copper in the Cohen diabetic rat. Ergaz Z, Guillemin C, Neeman-Azulay M, et al. Toxicol. Appl. Pharmacol. 276(3), 220-30, (2014)

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Involvement of reactive oxygen species in brominated diphenyl ether-47-induced inflammatory cytokine release from human extravillous trophoblasts in vitro. Park HR, Kamau PW, and Loch-Caruso R Toxicol. Appl. Pharmacol. 274(2), 283-92, (2014)

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Mitochondria oxidative stress, connexin43 remodeling, and sudden arrhythmic death. Sovari AA, Rutledge CA, Jeong EM, et al. Circ. Arrhythm. Electrophysiol. 6(3), 623-31, (2013)

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Chronic Tempol treatment restores pharmacological preconditioning in the senescent rat heart. Zhu J, Rebecchi MJ, Wang Q, et al. Am. J. Physiol. Heart Circ. Physiol. 304(5), H649-59, (2013)

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Blood pressure has only minor influence on aldosterone-induced oxidative stress and DNA damage in vivo. Queisser N, Amann K, Hey V, et al. Free Radic. Biol. Med. 54, 17-25, (2013)

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Blunted temporal activity of microvascular perfusion heterogeneity in metabolic syndrome: a new attractor for peripheral vascular disease? Butcher JT, Goodwill AG, Stanley SC, et al. Am. J. Physiol. Heart Circ. Physiol. 304(4), H547-58, (2013)

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Stable isotope- and mass spectrometry-based metabolomics as tools in drug metabolism: a study expanding tempol pharmacology. Li F, Pang X, Krausz KW, et al. J. Proteome Res. 12(3), 1369-76, (2013)

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BRCA1 mutations drive oxidative stress and glycolysis in the tumor microenvironment: implications for breast cancer prevention with antioxidant therapies. Martinez-Outschoorn UE, Balliet R, Lin Z, et al. Cell Cycle 11(23), 4402-13, (2012)

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NADPH oxidase 2-derived superoxide downregulates endothelial KCa3.1 in preeclampsia. Choi S, Kim JA, Na HY, et al. Free Radic. Biol. Med. 57, 10-21, (2013)

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NFAT is required for spontaneous pulmonary hypertension in superoxide dismutase 1 knockout mice. Ramiro-Diaz JM, Nitta CH, Maston LD, et al. Am. J. Physiol. Lung Cell. Mol. Physiol. 304(9), L613-25, (2013)

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Oxidative stress exaggerates skeletal muscle contraction-evoked reflex sympathoexcitation in rats with hypertension induced by angiotensin II. Koba S, Watanabe R, Kano N, et al. Am. J. Physiol. Heart Circ. Physiol. 304(1), H142-53, (2013)

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The carbonylation and covalent dimerization of human superoxide dismutase 1 caused by its bicarbonate-dependent peroxidase activity is inhibited by the radical scavenger tempol. Queiroz RF, Paviani V, Coelho FR, et al. Biochem. J. 455(1), 37-46, (2013)

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Modulation of the axon-reflex response to local heat by reactive oxygen species in subjects with chronic fatigue syndrome. Medow MS, Aggarwal A, Baugham I, et al. J. Appl. Physiol. 114(1), 45-51, (2013)

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Impaired L-arginine uptake but not arginase contributes to endothelial dysfunction in rats with chronic kidney disease. Martens CR, Kuczmarski JM, Lennon-Edwards S, et al. J. Cardiovasc. Pharmacol. 63(1), 40-8, (2014)

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Insulin mediated DNA damage in mammalian colon cells and human lymphocytes in vitro. Othman EM, Leyh A, and Stopper H Mutat. Res. 745-746, 34-9, (2013)

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Inhibition of reactive oxygen species in hypothalamic paraventricular nucleus attenuates the renin-angiotensin system and proinflammatory cytokines in hypertension. Su Q, Qin DN, Wang FX, et al. Toxicol. Appl. Pharmacol. 276(2), 115-20, (2014)

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Copper transporter ATP7A protects against endothelial dysfunction in type 1 diabetic mice by regulating extracellular superoxide dismutase. Sudhahar V, Urao N, Oshikawa J, et al. Diabetes 62(11), 3839-50, (2013)

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Thromboxane-induced renal vasoconstriction is mediated by the ADP-ribosyl cyclase CD38 and superoxide anion. Moss NG, Vogel PA, Kopple TE, et al. Am. J. Physiol. Renal Physiol. 305(6), F830-8, (2013)

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Targeting HIF2α translation with Tempol in VHL-deficient clear cell renal cell carcinoma. Sourbier C, Srivastava G, Ghosh MC, et al. Oncotarget 3(11), 1472-82, (2012)

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Endothelial dysfunction in gestational hypertension induced by catechol-O-methyltransferase inhibition. Hernandez M, Hernandez I, Rodriguez F, et al. Exp. Physiol. 98(3), 856-66, (2013)

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Testosterone enhances tubuloglomerular feedback by increasing superoxide production in the macula densa. Fu Y, Lu Y, Liu EY, et al. Am. J. Physiol. Regul. Integr. Comp. Physiol. 304(9), R726-33, (2013)

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Insulin alleviates posttrauma cardiac dysfunction by inhibiting tumor necrosis factor-α-mediated reactive oxygen species production. Feng Y, Liu Y, Wang D, et al. Crit. Care Med. 41(6), e74-84, (2013)

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Synthesis and study of 2-amino-7-bromofluorenes modified with nitroxides and their precursors as dual anti-amyloid and antioxidant active compounds. Tamás Kálai et al Eur. J. Med. Chem. 46, 1348-55, (2011)

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Ambient ultrafine particles reduce endothelial nitric oxide production via S-glutathionylation of eNOS. Du Y, Navab M, Shen M, et al. Biochem. Biophys. Res. Commun. 436(3), 462-6, (2013)

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Endogenous flow-induced superoxide stimulates Na/H exchange activity via PKC in thick ascending limbs. Hong NJ and Garvin JL Am. J. Physiol. Renal Physiol. 307(7), F800-5, (2014)

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The zebrafish--Danio rerio--is a useful model for measuring the effects of small-molecule mitigators of late effects of ionizing irradiation. Epperly MW, Bahary N, Quader M, et al. In Vivo 26(6), 889-97, (2012)

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Evaluation of antioxidative effects of sesamin on the in vivo hepatic reducing abilities by a radiofrequency ESR method. Tada M, Ono Y, Nakai M, et al. Anal. Sci. 29(1), 89-94, (2013)

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Effect of free radical scavenger on c-jun activation in rats with crush syndrome. Zhai W, Xu YF, Peng B, et al. Int. J. Clin. Pharmacol. Ther. 51(7), 600-5, (2013)

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DNA double-strand break repair genes and oxidative damage in brain metastasis of breast cancer. Woditschka S, Evans L, Duchnowska R, et al. J. Natl. Cancer Inst. 106(7), doi:10.1093/jnci/dju145, (2014)

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Merck 14,9141

Beil. 21,1,161

Fieser 9,247

FT-IR 2 (3), 3983:D / FT-IR 1 (2), 908:B / IR-Spectra (3), 216:H / IR-Spectra (2), 194:H / RegBook 1 (2), 2673:K / Sigma FT-IR 1 (2), 647:B / Structure Index 1, 420:D:4

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