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)

Flash point:

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)

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

TSCA 

Yes

HS Code 

29333999

Hazardous Substances Data

2226-96-2(Hazardous Substances Data)

Toxicity

LD50 oral in rat: 1053mg/kg

MSDS

• Language:English Provider:2,2,6,6-Tetramethyl freeagaoxy-4-piperidyl
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

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

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.

Uses

Spin label for EPR studies; phase transfer dehydration catalyst; antioxidant; inhibitor of olefin free radical polymerization.

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

Non flammable

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

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