A mycotoxin and an active metabolite of ochratoxin A
Related Products
Active Metabolite(s)
11439Ochratoxin A
Labeled Version(s)
40239Ochratoxin C-13C20
Parent Compound(s)
11439Ochratoxin A
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Ochratoxin C

Item No. 20183

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, ethyl ester
CAS Number
4865-85-4
Synonyms
  • Ochratoxin A ethyl ester
  • OTA ethyl ester
  • OTC
Molecular Formula
C22H22ClNO6
Formula Weight
431.9
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: SolubleDMSO: SolubleEthanol: SolubleMethanol: Soluble
SMILES
O=C1O[C@H](C)CC2=C1C(O)=C(C(N[C@H](C(OCC)=O)CC3=CC=CC=C3)=O)C=C2Cl
InChi Code
InChI=1S/C22H22ClNO6/c1-3-29-21(27)17(10-13-7-5-4-6-8-13)24-20(26)15-11-16(23)14-9-12(2)30-22(28)18(14)19(15)25/h4-8,11-12,17,25H,3,9-10H2,1-2H3,(H,24,26)/t12-,17+/m1/s1
InChi Key
BPZZWRPHVVDAPT-PXAZEXFGSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Ochratoxin C (OTC) is a mycotoxin that has been found in Aspergillus and is an active metabolite of OTA (Item No. 11439).1,2 It is formed from OTA by gut microbiota, however, OTA can also be formed from OTC in vivo.2,3 OTC inhibits the proliferation and differentiation of THP-1 monocytes (IC50s = 126 and 91 ng/ml, respectively) and induces apoptosis in the same cells when used at concentrations of 100 or 1,000 ng/ml.1 It induces mortality in zebrafish embryos (LC50 = 0.32 nM).4 OTC has been found in red wine.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Müller, G., Rosner, H., Rohrmann, B., et al. Effects of the mycotoxin ochratoxin A and some of its metabolites on the human cell line THP-1. Toxicology 184(1), 69-82 (2003).

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

    3. 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).

    4. Csenki, Z., Garai, E., Faisal, Z., et al. The individual and combined effects of ochratoxin A with citrinin and their metabolites (ochratoxin B, ochratoxin C, and dihydrocitrinone) on 2D/3D cell cultures, and zebrafish embryo models. Food Chem. Toxicol. 158, 112674 (2021).

    5. Remiro, R., Ibáñez-Vea, M., González-Peñas, E., et al. Validation of a liquid chromatography method for the simultaneous quantification of ochratoxin A and its analogues in red wines. J. Chromatogr. A 1217(52), 8249-8256 (2010).