A mycotoxin and an active metabolite of ochratoxin C
Related Products
Active Metabolite(s)
20183Ochratoxin C
Labeled Version(s)
31295Ochratoxin A-13C20
Parent Compound(s)
20183Ochratoxin C
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Ochratoxin A

Item No. 11439

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[[(3R)-5-chloro-3,4-dihydro-8-hydroxy-3-methyl-1-oxo-1H-2-benzopyran-7-yl]carbonyl]-L-phenylalanine
CAS Number
303-47-9
Synonyms
  • NSC 201422
  • NSC 221991
  • OTA
Molecular Formula
C20H18ClNO6
Formula Weight
403.8
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 10 mg/mlDMSO: 15 mg/mlEthanol: 50 mg/mlEthanol:PBS(pH 7.2) (1:1): 0.50 mg/ml
λmax
213, 331 nm
SMILES
O=C(O)C(NC(C1=CC(Cl)=C(C[C@@H](C)OC2=O)C2=C1O)=O)CC3=CC=CC=C3
InChi Code
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
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Ochratoxin A (OTA) is a mycotoxin that has been found in Penicillium and is an active metabolite of OTC (Item No. 20183).1,2,3 It is formed from OTC in vivo, however, OTC can also be formed from OTA by gut microbiota.1,4 OTA (120 μg/kg) increases renal lipid peroxide levels and the number of apoptotic cells, as well as reduces renal superoxide dismutase (SOD) activity in rats.2 Topical application of OTA (80 μg/animal) induces DNA damage, cell cycle arrest at the G0/G1 phase, and apoptosis in mouse skin cells.3 It also initiates tumor formation in a two-stage mouse skin tumorigenesis model. OTA has been found in food products and poultry feed.5,6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Fuchs, R., Hult, K., Peraica, M., et al. Conversion of ochratoxin C into ochratoxin A in vivo. Appl. Environ. Microbiol. 48(1), 41-42 (1984).

    2. Petrik, J., Zanić-Grubisić, T., Barisić, K., et al. Apoptosis and oxidative stress induced by ochratoxin A in rat kidney. Arch. Toxicol. 77(12), 685-693 (2003).

    3. Kumar, R., Ansari, K.M., Chaudhari, B.P., et al. Topical application of ochratoxin A causes DNA damage and tumor initiation in mouse skin. PLoS One 7(10), (2012).

    4. Galtier, P., and Alvinerie, M. In vitro transformation of ochratoxin A by animal microbioal floras. Ann. Rech. Vet. 7(1), 91-98 (1976).

    5. Al-Taher, F., Cappozzo, J., Zweigenbaum, J., et al. Detection and quantitation of mycotoxins in infant cereals in the U.S. market by LC-MS/MS using a stable isotope dilution assay. Food Control 72(Part A), 27-35 (2017).

    6. Ezekiel, C.N., Bandyopadhyay, R., Sulyok, M., et al. Fungal and bacterial metabolites in commercial poultry feed from Nigeria. Food Addit. Contam. Part A Chem. Anal. Control Expo. Risk Assess. 29(8), 1288-1299 (2012).