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188549

Sigma-Aldrich

2-Mercaptopyridin-N-oxid

99%

Synonym(e):

2-Pyridinthiol-1-oxid, Pyrithion

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About This Item

Empirische Formel (Hill-System):
C5H5NOS
CAS-Nummer:
1121-31-9
Molekulargewicht:
127.16
Beilstein:
109936
EG-Nummer:
214-329-4
MDL-Nummer:
MFCD00006196
UNSPSC-Code:
12352100
PubChem Substanz-ID:
24851166
NACRES:
NA.22

Assay

99%

mp (Schmelzpunkt)

69-72 °C (lit.)

SMILES String

[O-][n+]1ccccc1S

InChI

1S/C5H5NOS/c7-6-4-2-1-3-5(6)8/h1-4,8H

InChIKey

FGVVTMRZYROCTH-UHFFFAOYSA-N

Allgemeine Beschreibung

2-Mercaptopyridine N-oxide forms complexes on reaction with palladium chloride. It inhibits NADH-fumarate reductase purified from Trypanosoma cruzi. It is precursor to O-acyl thiohydroxamates. It ligates to metals to form biologically active complexes.

Anwendung

Precursor to O-acyl thiohydroxamates. Ligates to metals to form biologically active complexes.
2-Mercaptopyridine N-oxide was used to investigate the mechanism of photodegradation of mercaptopyridine-N-oxide biocides. It was used in ratiometric fluorescence imaging of intracellular zinc ions in mammalian cultures.

Piktogramme

Skull and crossbones
GHS06

Signalwort

Danger

Gefahreneinstufungen

Acute Tox. 3 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Zielorgane

Respiratory system

Lagerklassenschlüssel

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

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Analysenzertifikate (COA)

Lot/Batch Number
BGBC3720V
BGBB5606V
05015EJ
15408EH
25011LO

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Photodegradation of mercaptopyridine-N-oxide biocides.
R A Neihof et al.
Archives of environmental contamination and toxicology, 8(3), 355-368 (1979-01-01)
J. Chem. Res. Synop., 30-30 (1990)
Christopher J Chang et al.
Proceedings of the National Academy of Sciences of the United States of America, 101(5), 1129-1134 (2004-01-22)
Zinc is an essential metal ion for human growth and development, the disruption of cellular Zn(2+) homeostasis being implicated in several major disorders including Alzheimer's disease, diabetes, and cancer. The molecular mechanisms of Zn(2+) physiology and pathology are insufficiently understood
Vesna Lavtizar et al.
Ecotoxicology and environmental safety, 147, 132-138 (2017-08-26)
Copper pyrithione (CuPT) is a biocide, used worldwide to prevent biofouling on submerged surfaces. In aquatic environments it rapidly degrades, however, one of the degradation products (HPT) is known to react with cupric ion back to its parent compound. Not
J F Turrens et al.
FEMS microbiology letters, 175(2), 217-221 (1999-07-01)
The enzyme NADH-fumarate reductase is not found in mammalian cells but it is present in several parasitic protozoa including Trypanosoma cruzi, the parasite that causes Chagas' disease. This study shows that the drug 2-mercaptopyridine-N-oxide (MPNO) inhibits NADH-fumarate reductase purified from
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