3D Mol Similar

Tempol

: CAS No.: 2226-96-2; Molecular Weight：172.24; Modify Date.: 2022-12-06 15:23

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1. Names and Identifiers

: 1.1 Name; Tempol; 1.2 Synonyms; 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, FREE RADICAL 4-HYDROXY-2,2,6,6-TETRAMETHYLPIPERIDINYLOXY HYDROXY-TEMPO; View all

1.3 CAS No.: 2226-96-2

1.4 EINECS(EC#): 218-760-9

1.5 Molecular Formula: C9H18NO2* (isomer)

1.6 Inchi: InChI=1S/C9H18NO2/c1-8(2)5-7(11)6-9(3,4)10(8)12/h7,11H,5-6H2,1-4H3

1.7 InChIkey: UZFMOKQJFYMBGY-UHFFFAOYSA-N

1.8 Canonical Smiles: CC1(C)CC(O)CC(C)(C)N1[O]

1.9 Isomers Smiles: CC1(CC(CC(N1[O])(C)C)O)C

2. Properties

2.1 Density: 1.0402 (rough estimate)

2.1 Melting point: 69-71?°C(lit.)

2.1 Boiling point: 302.58°C (rough estimate)

2.1 Flash Point: 146°(295°F)

2.1 pKa: 5.07[at 20 ℃]

2.2 Water Solubility: In water, 2.86X10+4 mg/L at 25 °C (est)

2.3 StorageTemp: 2-8°C

3. Safety and Handling

3.1 Hazard Codes: Xn,Xi

3.1 Risk Statements: 22-36/37/38-36/38

3.1 Safety Statements: 26-36-37/39-36/37/39-27

3.1 WGK Germany: 1

3.1 RTECS: TN8991000

4. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

Serious eye damage, Category 1

Specific target organ toxicity \u2013 repeated exposure, Category 2

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Danger
Hazard statement(s)	H302 Harmful if swallowed H318 Causes serious eye damage H373 May cause damage to organs through prolonged or repeated exposure
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. P280 Wear protective gloves/protective clothing/eye protection/face protection. P260 Do not breathe dust/fume/gas/mist/vapours/spray.
Response	P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell. P330 Rinse mouth. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P310 Immediately call a POISON CENTER/doctor/\u2026 P314 Get medical advice/attention if you feel unwell.
Storage	none
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

5. NMR Spectrum

ESR : PHOSPHATE TRIRADICAL, IN THF, RT

ESR : SILICATE TETRARADICAL, IN THF, RT

ESR : SPIN LABELED CROWN ETHER/KSCN/ETHANOL, 77K

ESR : SPIN LABELED CROWN ETHER/KSCN/ETHANOL, HALF FIELD

ESR : SPIN LABELED CROWN ETHER/KSCN/ETHANOL, RT

ESR : SPIN LABELED WITH CU(II) PORPHYRIN, DRIED SAMPLE

ESR : SPIN LABELED WITH CU(II) PORPHYRIN, WET SAMPLE

ESR : SPIN LABELED WITH CU(II) PORPHYRIN, WET, Q-BAND

IR : KBr disc

IR : nujol mull

Mass

Mass spectrum (electron ionization)

6. Other Information

6.0 Merck: 14,9141

6.1 BRN: 1422990

6.2 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.

6.3 Chemical Properties: solid

6.4 Uses: A free radical scavenger

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

6.6 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.

6.7 Synthesis Reference(s): Synthetic Communications, 19, p. 3509, 1989 DOI: 10.1080/00397918908052760

6.8 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.

6.9 Flammability and Explosibility: Nonflammable

6.10 Biological Activity: Superoxide scavenger that displays neuroprotective, anti-inflammatory and analgesic effects.

6.11 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

7. Question & Answer

What are the Potential Benefits of 4-Hydroxy-2,2,6,6-tetramethyl-piperidinooxy? Jul 11 2023
General Description 4-Hydroxy-2,2,6,6-tetramethyl-piperidinooxy is a heterocyclic compound that is rapidly absorbed and distributed throughout the body. It has shown potential in preventing oxidative ..
What is Tempol and its role as an inhibitor? Dec 24 2022
Tempol, also known as 4-hydroxy-1-oxypiperidine, is a free radical oxygen inhibitor that is soluble in organic solvents such as ethanol, benzene, and water. It has a good inhibitory effect on acrylic ..
What is the chemical name, appearance, and packaging of Tempol? Oct 20 2020
Tempol, also known as Nitroxyl Free Radical Piperidinol, TBP, ZJ-701, Tri-n-butyl phosphate, Phosphoric acid tri-n-butyl ester, Tri-n-butyl phosphate, Flame retardant tri-n-butyl phosphate, has excell..
What is 4-Hydroxy-2,2,6,6-tetramethyl-piperidinooxy and its Applications? Nov 08 2019
4-Hydroxy-2,2,6,6-tetramethyl-piperidinooxy, also known as TEMPO derivative, is a heterocyclic compound commonly used as a catalyst and chemical oxidant due to its stability as a radical. Unlike TEMPO..

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