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188549

Sigma-Aldrich

2-Mercaptopyridine N-oxide

99%

Sinonimo/i:

2-Pyridinethiol-1-oxide, Pyrithione

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About This Item

Formula empirica (notazione di Hill):
C5H5NOS
Numero CAS:
1121-31-9
Peso molecolare:
127.16
Beilstein:
109936
Numero CE:
214-329-4
Numero MDL:
MFCD00006196
Codice UNSPSC:
12352100
ID PubChem:
24851166
NACRES:
NA.22

Saggio

99%

Punto di fusione

69-72 °C (lit.)

Stringa SMILE

[O-][n+]1ccccc1S

InChI

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

Descrizione generale

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.

Applicazioni

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.
Precursor to O-acyl thiohydroxamates. Ligates to metals to form biologically active complexes.

Pittogrammi

Skull and crossbones
GHS06

Avvertenze

Danger

Indicazioni di pericolo

H301,H315,H319,H335

Classi di pericolo

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

Organi bersaglio

Respiratory system

Codice della classe di stoccaggio

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

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

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

Certificati d'analisi (COA)

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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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