An anticancer agent
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COMC

Item No. 37736

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-butenoic acid, (6-oxo-1-cyclohexen-1-yl)methyl ester
CAS Number
106281-45-2
Synonyms
  • 2-Crotonyloxymethyl-2-cyclohexenone
Molecular Formula
C11H14O3
Formula Weight
194.2
Purity
≥90%
Formulation (Request formulation change)
A neat oil
Solubility(Learn about Variance in Solubility)
Acetonitrile: SolubleChloroform: SolubleDMSO: Soluble
SMILES
O=C(C=CC)OCC1=CCCCC1=O
InChi Code
InChI=1S/C11H14O3/c1-2-5-11(13)14-8-9-6-3-4-7-10(9)12/h2,5-6H,3-4,7-8H2,1H3
InChi Key
IQAJMALOOLNRLN-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    1 mg

    $729

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    Product Description

    COMC is an anticancer agent and a derivative of the bacterial metabolite COTC (Item No. 36408).1 It forms adducts with glutathione and nucleic acids.2,3 COMC inhibits the proliferation of B16 murine melanoma cells (IC50 = 0.041 µM).1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Joseph, E., Eiseman, J.L., Hamilton, D.S., et al. Molecular basis of the antitumor activities of 2-crotonyloxymethyl-2-cycloalkenones. J. Med. Chem. 46(1), 194-196 (2003).

    2. Joseph, E., Ganem, B., Eiseman, J.L., et al. Selective inhibition of MCF-7piGST breast tumors using glutathione transferase-derived 2-methylene-cycloalkenones. J. Med. Chem. 48(21), 6549-6552 (2005).

    3. Zhang, Q., Ding, Z., Creighton, D.J., et al. Alkylation of nucleic acids by the antitumor agent COMC. Org. Lett. 4(9), 1459-1462 (2002).