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ChemicalBook > Product Catalog >Analytical Chemistry >Standard >Spectral Standards >4-Hydroxy-2,2,6,6-tetramethyl-piperidinooxy

4-Hydroxy-2,2,6,6-tetramethyl-piperidinooxy

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CAS:2226-96-2
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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:4-HYDROXY-2,2,6,6-TETRAMETHYLPIPERIDINE-N-OXYL;4-HYDROXY-2,2,6,6-TETRAMETHYL-PIPERIDINOOXY;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-TEMPO, FREE RADICAL;2,2,6,6-Tetramethyl-4-hydroxypiperidine 1-oxyl;4-Hydroxy-2,2,6,6-tetramethyl-1-piperidin-1-yloxy, free radical
CAS:2226-96-2
MF:C9H18NO2*
MW:172.24
EINECS:218-760-9
Product Categories:Nitric Oxide Reagents;Spin Labeling Compounds;Inhibitors;Analytical Chemistry;ESR Spectrometry;Spin Labels;Heterocycles;2226-96-2
Mol File:2226-96-2.mol
4-Hydroxy-2,2,6,6-tetramethyl-piperidinooxy Structure
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
pka5.07[at 20 ℃]
color Orange
PH8.2 (20g/l, H2O, 20℃)
Water Solubility soluble
Merck 14,9141
BRN 1422990
Stability:Stable. Incompatible with strong oxidizing agents.
InChIKeyFAPCFNWEPHTUQK-UHFFFAOYSA-N
LogP0.56 at 25℃
CAS DataBase Reference2226-96-2(CAS DataBase Reference)
NIST Chemistry Reference1-Piperidinyloxy, 4-hydroxy-2,2,6,6-tetramethyl-(2226-96-2)
EPA Substance Registry System1-Piperidinyloxy, 4-hydroxy-2,2,6,6-tetramethyl- (2226-96-2)
Safety Information
Hazard Codes Xn,Xi
Risk Statements 22-36/37/38-36/38
Safety Statements 26-36-37/39-36/37/39-27
WGK Germany 1
RTECS TN8991000
Autoignition Temperature260°C (DIN 51794)
TSCA Yes
HS Code 29333999
Hazardous Substances Data2226-96-2(Hazardous Substances Data)
ToxicityLD50 oral in rat: 1053mg/kg
MSDS Information
ProviderLanguage
2,2,6,6-Tetramethyl freeagaoxy-4-piperidyl English
SigmaAldrich English
ACROS English
ALFA English
4-Hydroxy-2,2,6,6-tetramethyl-piperidinooxy Usage And Synthesis
DescriptionTEMPOL 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 Propertiessolid
UsesTempol, 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.
UsesA free radical scavenger
UsesSpin label for EPR studies; phase transfer dehydration catalyst; antioxidant; inhibitor of olefin free radical polymerization.
ApplicationIn 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 Description4-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 ExplosibilityNon flammable
Biological ActivitySuperoxide scavenger that displays neuroprotective, anti-inflammatory and analgesic effects.
storageStore at -20°C
References1) 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
Preparation Products6-Hydroxy-2-naphthaldehyde-->Bis(2,2,6,6-tetramethyl-1-piperidinyloxy-4-yl) sebacate
Tag:4-Hydroxy-2,2,6,6-tetramethyl-piperidinooxy(2226-96-2) Related Product Information
Haloperidol CHLOROPHOSPHONAZO III 1,2,2,6,6-Pentamethyl-4-piperidinol 2,2,6,6-Tetramethyl-4-piperidinol Drag-reduction agent Triacetonediamine 2,2,6,6-Tetramethylpiperidine Diethyl bis(2-hydroxyethyl)aminomethylphosphonate 9,10-Dihydro-9-oxa-10-phosphaphenanthrene 10-oxide 9,10-Dihydro-10-(2,3-dicarboxypropyl)-9-oxa-10-phosphaphenanthrene 10-oxide Octabenzone Piperazine-2-carboxylic acid dihydrochloride Tri(4-isopropylphenyl) phosphate 3-Hydroxyphenylphosphinyl-propanoic acid Triphenyl phosphate UV-1164 Tri-(4-hydroxy-TEMPO) phosphite SW606

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