| Identification | More | [Name]
4-Hydroxy-2,2,6,6-tetramethyl-piperidinooxy | [CAS]
2226-96-2 | [Synonyms]
2,2,6,6-TETRAMETHYL-4-HYDROXY-1-PIPERIDINYLOXY
2,2,6,6-TETRAMETHYL-4-PIPERIDINOL 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-TETRAMETHYLPIPERIDINE 1-OXYL
4-HYDROXY-2,2,6,6-TETRAMETHYLPIPERIDINE-N-OXYL
4-HYDROXY-2,2,6,6-TETRAMETHYL-PIPERIDINOOXY
4-HYDROXY-2,2,6,6-TETRAMETHYL-PIPERIDINOOXY, FREE RADICAL
4-HYDROXY-2,2,6,6-TETRAMETHYLPIPERIDINYLOXY
4-HYDROXY-2,2,6,6-TETRAMETHYLPIPERIDINYLOXY FREE RADICAL
4-HYDROXY-TEMPO
4-HYDROXY-TEMPO, FREE RADICAL
4-OH-TEMPO
HYDROXY-TEMPO
TEMPOL
1-Oxyl-2,2,6,6-tetramethyl-4-piperidinol
2,2,4,4-Tetramethyl-4-Piperidinol N-oxide
2,2,6,6-Tetramethyl-1,4-piperidinediol
2,2,6,6-Tetramethyl-4-hydroxypiperidin-1-oxyl
2,2,6,6-Tetramethyl-4-hydroxypiperidinooxy | [EINECS(EC#)]
218-761-4 | [Molecular Formula]
C9H18NO2 * | [MDL Number]
MFCD00006478 | [Molecular Weight]
172.24 | [MOL File]
2226-96-2.mol |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin .
R36/38:Irritating to eyes and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S37/39:Wear suitable gloves and eye/face protection .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S27:Take off immediately all contaminated clothing . | [WGK Germany ]
1
| [RTECS ]
TN8991000
| [Autoignition Temperature]
260°C (DIN 51794) | [TSCA ]
Yes | [HS Code ]
29333999 | [Hazardous Substances Data]
2226-96-2(Hazardous Substances Data) | [Toxicity]
LD50 oral in rat: 1053mg/kg |
| Hazard Information | Back Directory | [Description]
TEMPOL is a piperidine nitroxide and spin label with superoxide dismutase (SOD) mimetic activity.1,2,3 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.1 TEMPOL (1 mM) inhibits production of superoxide anions by 92% via a xanthine-xanthine oxidase reaction in vitro.2 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.3 | [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 |
| Spectrum Detail | Back Directory | [Spectrum Detail]
4-Hydroxy-2,2,6,6-tetramethyl-piperidinooxy(2226-96-2)MS
4-Hydroxy-2,2,6,6-tetramethyl-piperidinooxy(2226-96-2)IR1
4-Hydroxy-2,2,6,6-tetramethyl-piperidinooxy(2226-96-2)IR2
4-Hydroxy-2,2,6,6-tetramethyl-piperidinooxy(2226-96-2)Raman
4-Hydroxy-2,2,6,6-tetramethyl-piperidinooxy(2226-96-2)ESR
|
| Well-known Reagent Company Product Information | Back Directory | [Acros Organics]
4-Hydroxy-2,2,6,6-tetramethyl-piperidinooxy, free radical, 98%(2226-96-2) | [Alfa Aesar]
4-Hydroxy-TEMPO, free radical, 98+%(2226-96-2) | [Sigma Aldrich]
2226-96-2(sigmaaldrich) | [TCI AMERICA]
4-Hydroxy-2,2,6,6-tetramethylpiperidine 1-Oxyl Free Radical,>98.0%(GC)(2226-96-2) |
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