A bacterial metabolite with anticancer activity
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Isomer(s)
377466-epi COTC
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COTC

Item No. 36408

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-butenoic acid, [(3R,4R,5R)-3,4,5-trihydroxy-6-oxo-1-cyclohexen-1-yl]methyl ester
CAS Number
57449-30-6
Synonyms
  • 2-Crotonyloxymethyl-(4R,5R,6R)-4,5,6-trihydroxycyclohex-2-enone
Molecular Formula
C11H14O6
Formula Weight
242.2
Purity
≥90%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
DMSO: solubleMethanol: solubleWater: soluble
SMILES
CC=CC(OCC1=C[C@@H](O)[C@@H](O)[C@@H](O)C1=O)=O
InChi Code
InChI=1S/C11H14O6/c1-2-3-8(13)17-5-6-4-7(12)10(15)11(16)9(6)14/h2-4,7,10-12,15-16H,5H2,1H3/t7-,10-,11+/m1/s1
InChi Key
PSJQCAMBOYBQEU-ONOSFVFSSA-N
Origin
Bacterium/Streptomyces griseosporeus
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $556

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    Product Description

    COTC is a bacterial metabolite that has been found in S. griseosporeus and has anticancer activity.1 It inhibits glyoxalase in the presence of glutathione (GSH) in a concentration- and time-dependent manner. COTC inhibits the proliferation of HeLa cells (IC50 = 18 µg/ml), as well as reduces tumor growth and improves survival in an Ehrlich murine spontaneous adenocarcinoma model.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Takeuchi, T., Chimura, H., Hamada, M., et al. A glyoxalase I inhibitor of a new structural type produced by Streptomyces. J. Antibiot. (Tokyo) 28(1), 737-742 (1975).