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O1877

Sigma-Aldrich

Ochratoxin A

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

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C20H18ClNO6
CAS Number:
303-47-9
Molecular Weight:
403.81
Beilstein:
1301486
MDL number:
MFCD00078079
UNSPSC Code:
12352200
PubChem Substance ID:
24897954
NACRES:
NA.77

product name

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

biological source

Petromyces albertensis

Quality Level

300

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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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.

Preparation Note

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

Pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

Signal Word

Danger

Hazard Statements

H300,H351

Hazard Classifications

Acute Tox. 2 Oral - Carc. 2

Storage Class Code

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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Chong-Sun Khoi et al.
International journal of molecular sciences, 22(20) (2021-10-24)
Ochratoxin A (OTA), one of the major food-borne mycotoxins, impacts the health of humans and livestock by contaminating food and feed. However, the underlying mechanism of OTA nephrotoxicity remains unknown. This study demonstrated that OTA induced apoptosis through selective endoplasmic
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
Shanel Raghubeer et al.
Toxicology in vitro : an international journal published in association with BIBRA, 57, 211-216 (2019-03-17)
Cellular adaptation to hypoxia is controlled by hypoxia-inducible factor 1α (HIF1α), a transcription factor activated in response to oxygen tension, reactive oxygen species (ROS) and inflammation. Overexpression of HIF1α and HSP90 has been associated with cancer induction. Ochratoxin A (OTA)
H Schramek et al.
The Journal of pharmacology and experimental therapeutics, 283(3), 1460-1468 (1998-02-12)
The kidneys represent one of the main targets of ochratoxin A (OTA), a secondary fungal metabolite that is produced by certain species of Aspergillus and Penicillium. OTA has the ability to disturb Madin-Darby canine kidney (MDCK) cell pH homeostasis, leading
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
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