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80126

N-tert-Butyl-α-phenylnitrone

for ESR-spectroscopy

Synonym(s):

N-Benzylidene-tert-butylamine N-oxide, PBN, Phenyl N-t-butylnitrone

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About This Item

Linear Formula:
C6H5CH=N(O)C(CH3)3
CAS Number:
3376-24-7
Molecular Weight:
177.24
UNSPSC Code:
23151816
NACRES:
NA.21
PubChem Substance ID:
329768721
EC Number:
222-168-6
Beilstein/REAXYS Number:
2044028
MDL number:
MFCD00008799

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Product Name

N-tert-Butyl-α-phenylnitrone, for ESR-spectroscopy

InChI

1S/C11H15NO/c1-11(2,3)12(13)9-10-7-5-4-6-8-10/h4-9H,1-3H3/b12-9-

InChI key

IYSYLWYGCWTJSG-XFXZXTDPSA-N

SMILES string

CC(C)(C)[N+](\[O-])=C\c1ccccc1

assay

≥99.5% (HPLC)

form

powder

mp

72-74 °C
73-74 °C (lit.)

solubility

chloroform: 50 mg/mL, clear, colorless

storage temp.

−20°C

Quality Level

100

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This Item
B7263215430203995
N-tert-Butyl-α-phenylnitrone for ESR-spectroscopy

Supelco

80126

N-tert-Butyl-α-phenylnitrone

N-tert-Butyl-α-phenylnitrone ≥98% (GC)

Sigma-Aldrich

B7263

N-tert-Butyl-α-phenylnitrone

α-(4-Pyridyl N-oxide)-N-tert-butylnitrone 99%

Sigma-Aldrich

215430

α-(4-Pyridyl N-oxide)-N-tert-butylnitrone

N-tert-Butyl-α-phenylnitrone Most commonly-used free radical trap.

Sigma-Aldrich

203995

N-tert-Butyl-α-phenylnitrone

assay

≥99.5% (HPLC)

assay

≥98% (GC)

assay

99%

assay

≥98% (GC)

Quality Level

100

Quality Level

100

Quality Level

-

Quality Level

100

form

powder

form

powder

form

solid

form

solid

solubility

chloroform: 50 mg/mL, clear, colorless

solubility

DMSO: soluble

solubility

water: soluble 10 mg/mL, clear, colorless to faintly yellow

solubility

DMSO: 10 mg/mL, water: 20 mg/mL, chloroform: 50 mg/mL

storage temp.

−20°C

storage temp.

−20°C

storage temp.

-

storage temp.

−20°C

mp

72-74 °C, 73-74 °C (lit.)

mp

73-74 °C (lit.)

mp

183-185 °C (lit.)

mp

-

Application

N-tert-Butyl-a-phenylnitrone was used as spin trapping agent during measurement of scavenging rate constant of carotenoid using EPR spin-trapping technique.[1] This reagent helps in obtaining a six-line ESR spectrum and hyperfine coupling constants, confirming the presence of carbon-based radical in uric acid and peroxynitrite, using electron spin resonance spectroscopy and liquid chromatography mass spectrometry.[2]

Biochem/physiol Actions

N-tert-butyl-α-phenylnitrone (PBN) is a commonly used free-radical spin trap.
N-tert-butyl-α-phenylnitrone (PBN) is a commonly used free-radical spin trap. It has been shown to reduce the number of emboli-induced cerebral microinfarctions in the rabbit cortex and prevent neoplasia by its radical scavenging activity and its ability to inhibit cyclooxygenase-2 activity. Reported to inhibit the induction of nitric oxide synthase (iNOS), thereby preventing the overproduction of nitric oxide (NO). PBN in a dose of 100 mg/kg i.p. reduced necrosis of the substantia nigra, pars reticulate in flurothyl-induced status epilepticus in rats. It protects against some types of post-trauma epileptogenic events in an animal model of epilepsy. The lethal dose of PBN in rats was found to be approximately 100 mg/100 g body weight (0.564 mmol/100Å g).

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
BCCK8009
BCCK5296
BCCH0777
BCCG4640
BCCD3805

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Radicals in the reaction between peroxynitrite and uric acid identified by electron spin resonance spectroscopy and liquid chromatography mass spectrometry.
Imaram W
Free Radical Biology & Medicine, 49(2), 275-281 (2010)
Antioxidant and redox properties of supramolecular complexes of carotenoids with beta-glycyrrhizic acid.
Polyakov NE
Free Radical Biology & Medicine, 40(10), 1804-1809 (2006)
Zhen Wang et al.
Toxicology and applied pharmacology, 259(2), 236-247 (2012-01-19)
The placenta is essential for sustaining the growth of the fetus. An increased endoplasmic reticulum (ER) stress has been associated with the impaired placental and fetal development. Cadmium (Cd) is a potent teratogen that caused fetal malformation and growth restriction.
Ritesh P Daya et al.
Brain research, 1412, 28-36 (2011-08-06)
Haloperidol (HP) is a widely prescribed antipsychotic drug used for the treatment of mental disorders. However, while providing therapeutic benefits, this drug also causes serious extrapyramidal side effects, such as tardive dyskinesia (TD). Upon chronic administration, HP causes behavioural supersensitivity
Mark C Fogarty et al.
Environmental and molecular mutagenesis, 52(1), 35-42 (2010-09-15)
Exercise-induced deoxyribonucleic acid (DNA) damage is often associated with an increase in free radicals; however, there is a lack of evidence examining the two in parallel. This study tested the hypothesis that high-intensity exercise has the ability to produce free
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