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Sigma-Aldrich

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

99%

Synonym(s):

N-(4-Pyridylmethylene)-tert-butylamine N,N′-dioxide, N-tert-Butyl-α-(4-pyridyl)nitrone N′-oxide, POBN

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About This Item

Empirical Formula (Hill Notation):
C10H14N2O2
CAS Number:
66893-81-0
Molecular Weight:
194.23
Beilstein/REAXYS Number:
1453764
EC Number:
266-512-3
MDL number:
MFCD00041022
UNSPSC Code:
12352100
PubChem Substance ID:
24852894
NACRES:
NA.22

assay

99%

form

solid

mp

183-185 °C (lit.)

solubility

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

SMILES string

CC(C)(C)\[N+]([O-])=C/c1cc[n+]([O-])cc1

InChI

1S/C10H14N2O2/c1-10(2,3)12(14)8-9-4-6-11(13)7-5-9/h4-8H,1-3H3/b12-8+

InChI key

RNRMWTCECDHNQU-XYOKQWHBSA-N

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Application

α-(4-Pyridyl N-oxide)-N-tert-butylnitrone was used as spin trapping agent to detect:
  • the formation of hydroxyl radical adducts during decomposition of hydrogen peroxide in the presence of nickel (II) oligopeptides
  • hydroxyl radicals and selenide radical anions
Spin trap reagent used to measure ethanol oxidation to 1-hydroxyethyl radical (HER) which can bind to protein. Has also been used in studies of DNA methylation, iron-mediated polyunsaturated fatty acid peroxidation, and free-radical formation by Alzheimer β-amyloid peptide. The formation of hydroxyl radical in chondrocytes and cartilage has been detected using POBN.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Measurement of hydroxyl radical activity in a soil slurry using the spin trap a-(4-pyridyl-1-oxide)-N-tert-butylnitrone.
Huling SG, et al.
Environmental Science & Technology, 32(21), 3436-3441 (1998)
J. Photochem. Photobiol., A, 56, 89-89 (1991)
Bulletin of the Chemical Society of Japan, 64, 1976-1976 (1991)
Andrew E Maclean et al.
PLoS pathogens, 17(3), e1009301-e1009301 (2021-03-03)
The mitochondrial electron transport chain (mETC) and F1Fo-ATP synthase are of central importance for energy and metabolism in eukaryotic cells. The Apicomplexa, important pathogens of humans causing diseases such as toxoplasmosis and malaria, depend on their mETC in every known
S Inoue et al.
Biochemical and biophysical research communications, 159(2), 445-451 (1989-03-15)
ESR studies using spin traps, 5,5-dimethylpyrroline-N-oxide and alpha-(4-pyridyl 1-oxide)-N-tert-butylnitrone, revealed that hydroxyl radical adducts are produced by the decomposition of hydrogen peroxide in the presence of nickel(II) oligopeptides. Order of catalytic activities of nickel(II) oligopeptides used in the production of
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