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ChemicalBook--->CAS DataBase List--->2226-96-2

2226-96-2

2226-96-2 Structure

2226-96-2 Structure
IdentificationMore
[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
Chemical PropertiesBack Directory
[Appearance]

solid
[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℃)
[Stability:]

Stable. Incompatible with strong oxidizing agents.
[Water Solubility ]

soluble
[Merck ]

9141
[BRN ]

1422990
[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]

2226-96-2(EPA Substance)
Safety DataBack 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
Material Safety Data Sheet(MSDS)Back Directory
[msds information]

2,2,6,6-Tetramethyl freeagaoxy-4-piperidyl(2226-96-2).msds
Hazard InformationBack Directory
[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
Spectrum DetailBack 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 InformationBack 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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