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O1877

Sigma-Aldrich

Ochratoxin A

from Petromyces albertensis, ≥98% (HPLC), powder, mycotoxin

Synonyme(s) :

N-[(3R)-(5-Chloro-8-hydroxy-3-methyl-1-oxo-7-isochromanyl)carbonyl]-L-phenylalanine

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About This Item

Formule empirique (notation de Hill) :
C20H18ClNO6
Numéro CAS:
303-47-9
Poids moléculaire :
403.81
Beilstein:
1301486
Numéro MDL:
MFCD00078079
Code UNSPSC :
12352200
ID de substance PubChem :
24897954
Nomenclature NACRES :
NA.77

Nom du produit

Ochratoxin A, from Petromyces albertensis, ≥98% (HPLC)

Source biologique

Petromyces albertensis

Niveau de qualité

300

Essai

≥98% (HPLC)

Forme

powder

Impuretés

Benzene, free

Solubilité

ethanol: soluble

Mode d’action

enzyme | inhibits
protein synthesis | interferes

Température de stockage

2-8°C

Chaîne SMILES 

C[C@@H]1Cc2c(Cl)cc(c(O)c2C(=O)O1)C(=O)N[C@@H](Cc3ccccc3)C(O)=O

InChI

1S/C20H18ClNO6/c1-10-7-12-14(21)9-13(17(23)16(12)20(27)28-10)18(24)22-15(19(25)26)8-11-5-3-2-4-6-11/h2-6,9-10,15,23H,7-8H2,1H3,(H,22,24)(H,25,26)/t10-,15+/m1/s1

Clé InChI

RWQKHEORZBHNRI-BMIGLBTASA-N

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Catégories apparentées

Application

Ochratoxin A has been used as a mycotoxin:
  • to test its effect on metabolism and hypoxia in human embryonic kidney (HEK293) cells
  • to test its cytotoxic effects in bovine mammary epithelial cells
  • as a standard for gamma radiation studies with food products and in cytotoxic studies using Hep G2 cells

Actions biochimiques/physiologiques

Ochratoxin A (OTA), a renal toxin, is produced majorly by Aspergillus and Penicillium fungal species. It is immunotoxic, teratogenic myelotoxic, and mutagenic. It effectively interrupts the intestinal barrier functions. OTA displays a long elimination half-life and stimulates the major inflammatory cytokines release.
Ochratoxin A is a mycotoxin found in food that is nephrotoxic and carcinogenic in the kidney and induces differentiation in cloned renal cell lines. Increases endoplasmic reticulum ATP-dependent Ca2+ pump activity.

Notes préparatoires

This product is also soluble in chloroform (9.80 - 10.20 mg/ml), methanol (10 mg/ml), ethanol (50 mM), and DMSO (100 mM).

Pictogrammes

Skull and crossbonesHealth hazard
GHS06,GHS08

Mention d'avertissement

Danger

Mentions de danger

H300,H351

Classification des risques

Acute Tox. 2 Oral - Carc. 2

Code de la classe de stockage

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificats d'analyse (COA)

Lot/Batch Number
089M4145V
14190609
067M4011V
059M4100V
14181021

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Consulter la Bibliothèque de documents

J R Welborn et al.
Journal of the American Society of Nephrology : JASN, 9(11), 1973-1982 (1998-11-10)
Epifluorescence microscopy was used to study peritubular transport of the fluorescent mycotoxin ochratoxin A (OTA) into single proximal tubule segments of the rabbit. Initial rates of OTA uptake into S2 segments were saturable and adequately described by Michaelis-Menten kinetics, with
A Pfohl-Leszkowicz et al.
Molecular carcinogenesis, 23(2), 76-85 (1998-11-10)
Ochratoxin A (OTA), a nephrotoxic and carcinogenic mycotoxin, is implicated in the etiology of Balkan endemic nephropathy (BEN), a chronic disease affecting populations in the Balkans. Patients suffering from Balkan endemic nephropathy, urinary-tract tumors, or both are more frequently extensive
I Baudrimont et al.
Toxicology, 89(2), 101-111 (1994-04-18)
Ochratoxin A (OTA) is a mycotoxin produced by Aspergillus ochraceus as well as other molds. It is a natural contaminant of mouldy food and feed. OTA has a number of toxic effects, the most prominent being nephrotoxicity. Furthermore, OTA is
A Dörrenhaus et al.
Archives of toxicology, 71(11), 709-713 (1997-01-01)
In cultured rat hepatocytes the mycotoxin ochratoxin A (OTA) induced unscheduled DNA synthesis (UDS) only in a narrow concentration range. Using a culture medium supplemented with 1% fetal calf serum, at 750 nM OTA a weak induction and at 1
D Hoehler et al.
Biochimica et biophysica acta, 1357(2), 225-233 (1997-06-27)
Oxidative damage may be one of the manifestations of cellular damage in the toxicity of ochratoxin A (OA). OA; its three natural analogs, OB, OC and O alpha; and three synthetic analogs, the ethyl amide of OA (OE-OA), O-methylated OA
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