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| | 4-Hydroxy-2,2,6,6-tetramethyl-piperidinooxy Basic information |
| Product Name: | 4-Hydroxy-2,2,6,6-tetramethyl-piperidinooxy | | Synonyms: | HYDROXY-TEMPO;4-HYDROXY-2,2,6,6-TETRAMETHYLPIPERIDINE-N-OXYL;4-HYDROXY-2,2,6,6-TETRAMETHYL-PIPERIDINOOXY;4-HYDROXY-2,2,6,6-TETRAMETHYLPIPERIDINE 1-OXYL;4-HYDROXY-2,2,6,6-TETRAMETHYL-1-PIPERIDIN-1-YLOXY;4-HYDROXY-2,2,6,6-TETRAMETHYL-1-PIPERIDINYLOXY, FREE RADICAL;4-HYDROXY-2,2,6,6-TETRAMETHYL-PIPERIDINOOXY, FREE RADICAL;4-HYDROXY-2,2,6,6-TETRAMETHYLPIPERIDINYLOXY | | CAS: | 2226-96-2 | | MF: | C9H18NO2* | | MW: | 172.24 | | EINECS: | 218-760-9 | | Product Categories: | Inhibitors;Analytical Chemistry;ESR Spectrometry;Spin Labels;Heterocycles;Nitric Oxide Reagents;Spin Labeling Compounds;2226-96-2 | | Mol File: | 2226-96-2.mol |  |
| | 4-Hydroxy-2,2,6,6-tetramethyl-piperidinooxy Chemical Properties |
| Melting point | 69-71 °C(lit.) | | Boiling point | 302.58°C (rough estimate) | | density | 1.0402 (rough estimate) | | vapor pressure | 0.025Pa at 20℃ | | refractive index | 1.4350 (estimate) | | Fp | 146°(295°F) | | storage temp. | 2-8°C | | solubility | 1670g/l | | form | Crystals or Crystalline Powder | | pka | 5.07[at 20 ℃] | | color | Orange | | PH | 8.2 (20g/l, H2O, 20℃) | | Water Solubility | soluble | | Merck | 14,9141 | | BRN | 1422990 | | Stability: | Stable. Incompatible with strong oxidizing agents. | | InChIKey | FAPCFNWEPHTUQK-UHFFFAOYSA-N | | LogP | 0.56 at 25℃ | | CAS DataBase Reference | 2226-96-2(CAS DataBase Reference) | | NIST Chemistry Reference | 1-Piperidinyloxy, 4-hydroxy-2,2,6,6-tetramethyl-(2226-96-2) | | EPA Substance Registry System | 1-Piperidinyloxy, 4-hydroxy-2,2,6,6-tetramethyl- (2226-96-2) |
| | 4-Hydroxy-2,2,6,6-tetramethyl-piperidinooxy Usage And Synthesis |
| Description | TEMPOL is a piperidine nitroxide and spin label with superoxide dismutase (SOD) mimetic activity. It inhibits lipid peroxidation in rat liver microsomes with 50% inhibition of microsomal lipid peroxidation (IP50) values of 117, 61, and 381 μM for peroxidation induced by iron plus NADPH, iron plus ascorbate, and t-butylhydroperoxide, respectively. TEMPOL (1 mM) inhibits production of superoxide anions by 92% via a xanthine-xanthine oxidase reaction in vitro. It reduces mean arterial pressure and heart rate in spontaneously hypertensive rats (ED50s = 70 and 63 μmol/kg, respectively) when administered intravenously. TEMPOL is a cell-permeable spin label that has been used to quantify intracellular oxygen in various cell types by electron spin resonance (ESR) spectroscopy. | | Chemical Properties | solid | | Uses | A free radical scavenger | | Uses | Spin label for EPR studies; phase transfer dehydration catalyst; antioxidant; inhibitor of olefin free radical polymerization. | | Uses | Tempol, a water-soluble piperidine nitroxide derivative having nonspecific radical-scavenging and superoxide dismutase (SOD) activity, protects cultured aerobic, but not hypoxic, cells against radiation-induced killing. Protection does not depend on intracellular thiols and does not involve O2-depletion. Tempol reacts with peroxyl radicals and can also oxidize DNA-bound metal ions, thereby interfering with OH? generation. | | Application | 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. | | Synthesis Reference(s) | Synthetic Communications, 19, p. 3509, 1989 DOI: 10.1080/00397918908052760 | | General Description | 4-Hydroxy-TEMPO is a 4-substituted 2,2,6,6-tetramethylpiperidyl-1-oxy (TEMPO) derivative. It is a low-molecular weight compound and has been proposed as superoxide dismutase mimic. | | Flammability and Explosibility | Nonflammable | | Biological Activity | Superoxide scavenger that displays neuroprotective, anti-inflammatory and analgesic effects. | | storage | Store at -20°C | | References | 1) Lipman et al. (2006), Neuroprotective effects if the stable nitroxide compound Tempol in 1-methyl-4-phenylpyridinium ion-induced neurotoxicity in the Nerve Growth Factor-differentiated model of pheochromocytoma PC12? cells; Eur. J. Pharmacol., 549 50
2) Guron et al. (2006), Acute effects of the superoxide dismutase mimetic tempol on split kidney function in two-kidney one-clip hypertensive rats; J. Hypertens., 24 387
3) Samuni and Barenholz (1997), Gamma-irradiation damage to liposomes differing in composition and their protection by nitroxides; Free Radic. Biol. Med., 23 972
4) Bernardy et al. (2017), Tempol, a Superoxide Dismutase Mimetic Agent, Inhibits Superoxide Anion-Induced Inflammatory Pain in Mice; Biomed. Res. Int., 2017 9584819
5) De Blasio et al. (2017), The superoxide dismutase mimetic tempol blunts diabetes-induced upregulation of NADPH oxidase and endoplasmic reticulum stress in a rat model of diabetic nephropathy; Eur. J. Pharmacol., 807 12 |
| | 4-Hydroxy-2,2,6,6-tetramethyl-piperidinooxy Preparation Products And Raw materials |
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