An isoprenoid antibiotic and antiviral
Technical Support & Resources

Information provided in the product description is from published literature. Due to the nature of scientific experimentation, your results (e.g., selectivity and effective concentrations) or specific application for this product may differ. If you have questions about how this product fits your application, please contact our technical support staff.

Visit our FAQ

Contact Us

Toll Free Phone (USA and Canada Only): (888) 526-5351
Direct Phone: (734) 975-3888

Request Technical Support

Technical Support Request

To streamline the process attach the appropriate questionnaire to your inquiry.

Download IHC QuestionnaireDownload WB Questionnaire

View Our Privacy Statement for details on how we use and protect your data. In addition, this site is protected by hCaptcha and its Privacy Policy and Terms of Service apply.

Ascochlorin

Item No. 19437

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3-chloro-4,6-dihydroxy-2-methyl-5-[(2E,4E)-3-methyl-5-[(1R,2R,6R)-1,2,6-trimethyl-3-oxocyclohexyl]-2,4-pentadien-1-yl]-benzaldehyde
CAS Number
26166-39-2
Synonyms
  • Antibiotic LL-Z1272γ
  • Ilicicolin D
  • NSC 287492
Molecular Formula
C23H29ClO4
Formula Weight
404.9
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: SolubleDMSO: SolubleEthanol: SolubleMethanol: Soluble
SMILES
OC1=C(Cl)C(C)=C(C([H])=O)C(O)=C1C/C=C(C)/C=C/[C@]2(C)[C@@H](C)C(CC[C@H]2C)=O
InChi Code
InChI=1S/C23H29ClO4/c1-13(10-11-23(5)14(2)7-9-19(26)16(23)4)6-8-17-21(27)18(12-25)15(3)20(24)22(17)28/h6,10-12,14,16,27-28H,7-9H2,1-5H3/b11-10+,13-6+/t14-,16+,23+/m1/s1
InChi Key
SETVRSKZJJWOPA-FLDGXQSCSA-N
Origin
Fungus/Acremonium sp.
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Recommended Products
Certificates of Analysis & Batch Specific Data

Provide batch numbers separated by commas to download or request available product inserts, QC sheets, certificates of analysis, data packs, and GC-MS data.

Download most recent Certificate of Analysis for this product

    500 µg

    $317

    Add

    2.5 mg

    $1,262

    Add
    Cayman Chemical
    Visit Our Cancer Resource Center
    Find Tools & Resources to Study the Hallmarks of Cancer
    • Cancer cell signaling & regulation
    • Cancer metabolism
    • Tumor microenvironment
    EXPLORE NOW
    Product Description

    Ascochlorin is an isoprenoid antibiotic and antiviral that has diverse effects on mammalian cells.1,2 It suppresses PMA-induced invasion in renal carcinoma cells (IC50 = ~10 µM) by inhibiting the expression of matrix metalloproteinase-9.3 At 2 µM, ascochlorin profoundly increases the expression of p53 by increasing protein stability in cancer cells, and, at 50 µm, it inhibits signaling through STAT3.4,5 Ascochlorin also binds and inhibits the mitochondrial cytochrome bc1 complex, blocking reduction of cytochrome b by ubiquinone.6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Tamura, G., Suzuki, S., Takatsuki, A., et al. Ascochlorin, a new antibiotic, found by the paper-disc agar-diffusion method. I. Isolation, biological and chemical properties of ascochlorin. (Studies on antiviral and antitumor antibiotics. I). J. Antibiot. (Tokyo) 21(9), 539-544 (1968).

    2. Takatsuki, A., Tamura, G., and Arima, K. Antiviral and antitumor antibiotics. XIV. Effects of ascochlorin and other respiration inhibitors on multiplication of Newcastle disease virus in cultured cells. App. Microbiol. 17(6), 825-829 (1969).

    3. Hong, S., Park, K.K., Magae, J., et al. Ascochlorin inhibits matrix metalloproteinase-9 expression by suppressing activator protein-1-mediated gene expression through the ERK1/2 signaling pathway: Inhibitory effects of ascochlorin on the invasion of renal carcinoma cells. The Journal of Biological Chemisty 280(26), 25202-20209 (2005).

    4. Jeong, J.H., Nakajima, H., Magae, J., et al. Ascochlorin activates p53 in a manner distinct from DNA damaging agents. Int. J. Cancer 124(12), 2797-2803 (2009).

    5. Dai, X., Ahn, K.S., Kim, C., et al. Ascochlorin, an isoprenoid antibiotic inhibits growth and invasion of hepatocellular carcinoma by targeting STAT3 signaling cascade through the induction of PIAS3. Mol.Oncol. 9(4), 818-833 (2015).

    6. Berry, E.A., Huang, L.s., Lee, D.W., et al. Ascochlorin is a novel, specific inhibitor of the mitochondrial cytochrome bc1 complex. Biochim. Biophys. Acta 1797(3), 360-370 (2016).