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

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

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

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H302Harmful if swallowed

H318Causes serious eye damage

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P501Dispose of contents/container to..…

4-Hydroxy-2,2,6,6-tetramethyl-piperidinooxy Chemical Properties,Usage,Production

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