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O1877

Sigma-Aldrich

Ochratoxin A

from Petromyces albertensis, ≥98% (HPLC)

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Synonym(s):
N-[(3R)-(5-Chloro-8-hydroxy-3-methyl-1-oxo-7-isochromanyl)carbonyl]-L-phenylalanine
Empirical Formula (Hill Notation):
C20H18ClNO6
CAS Number:
Molecular Weight:
403.81
Beilstein/REAXYS Number:
1301486
MDL number:
PubChem Substance ID:
NACRES:
NA.77

biological source

Petromyces albertensis

Quality Level

assay

≥98% (HPLC)

form

powder

impurities

Benzene, free

solubility

ethanol: soluble

mode of action

enzyme | inhibits
protein synthesis | interferes

storage temp.

2-8°C

SMILES string

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

InChI key

RWQKHEORZBHNRI-BMIGLBTASA-N

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1 of 4

This Item
CRM46912O3007494128
Ochratoxin A from Petromyces albertensis, ≥98% (HPLC)

O1877

Ochratoxin A

Ochratoxin A solution certified reference material, 50 μg/mL in benzene: acetic acid (99:1), ampule of 1 mL

CRM46912

Ochratoxin A solution

Ochratoxin A Ochratoxin A (OTA) is a mycotoxin that acts through mechanisms such as the inhibition of protein synthesis, and may also be mediated by organic anion transporters (OATs).

494128

Ochratoxin A

form

powder

form

-

form

-

form

powder

Quality Level

300

Quality Level

-

Quality Level

200

Quality Level

100

storage temp.

2-8°C

storage temp.

-10 to -25°C

storage temp.

2-8°C

storage temp.

2-8°C

solubility

ethanol: soluble

solubility

-

solubility

-

solubility

DMSO: 50 mg/mL, nearly colorless

biological source

Petromyces albertensis

biological source

-

biological source

-

biological source

-

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

Biochem/physiol Actions

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.

pictograms

Skull and crossbonesHealth hazard

signalword

Danger

Hazard Classifications

Acute Tox. 2 Oral - Carc. 2

Storage Class

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

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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


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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
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
C E Groves et al.
Journal of the American Society of Nephrology : JASN, 10(1), 13-20 (1999-01-16)
Primary cultures of rabbit renal proximal tubule cells grown under improved culture conditions were used to study the transepithelial transport of the nephrotoxic mycotoxin ochratoxin A. The basal-to-apical transepithelial flux, i.e., secretion, of this fluorescence organic acid was measured in
X Chong et al.
Biochemical pharmacology, 44(7), 1401-1409 (1992-10-06)
A disruption of calcium homeostasis, leading to a sustained increase in cytosolic calcium levels, has been associated with cytotoxicity in response to a variety of agents in different cell types. We have observed that administration of a single high dose
M Gekle et al.
Toxicology and applied pharmacology, 152(1), 282-291 (1998-10-17)
Ochratoxin A (OTA) is a ubiquitous fungal metabolite with predominant nephrotoxic action. OTA impairs postproximal renal electrolyte handling and increases the incidence of renal adenoma and carcinoma. Furthermore, it is supposed to be involved in the pathogenesis of different forms

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