A prenylated 4-hydroxycoumarin
Related Products
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.

Ferulenol

Item No. 19568

Technical Information
Formal Name
4-hydroxy-3-[(2E,6E)-3,7,11-trimethyl-2,6,10-dodecatrien-1-yl]-2H-1-benzopyran-2-one
CAS Number
6805-34-1
Molecular Formula
C24H30O3
Formula Weight
Purity
≥95%
A solid
DMSO: SolubleEthanol: SolubleMethanol: Soluble
SMILES
O=C1C(C/C=C(C)/CC/C=C(C)/CC/C=C(C)/C)=C(O)C2=CC=CC=C2O1
InChi Code
InChI=1S/C24H30O3/c1-17(2)9-7-10-18(3)11-8-12-19(4)15-16-21-23(25)20-13-5-6-14-22(20)27-24(21)26/h5-6,9,11,13-15,25H,7-8,10,12,16H2,1-4H3/b18-11+,19-15+
InChi Key
NJJDBBUWWOAOLD-CFBAGHHKSA-N
Origin
Plant/Ferula communis
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.

    Add

    Add

    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

    Ferulenol is a prenylated 4-hydroxycoumarin first isolated from F. communis that demonstrates potent antimycobacterial activity.1 It does not directly affect blood coagulation but at concentrations less than 100 nM has been shown to impair factor X biosynthesis.2 Ferulenol has also been shown to stimulate tubulin polymerization in vitro, rearranging cellular microtubule networks into short fibers and altering nuclear morphology, which leads to cytotoxicity in various human tumor cell lines.3 Ferulenol is reported to disrupt oxidative phosphorylation, inhibiting succinate ubiquinone reductase without altering succinate dehydrogenase activity of complex II of the electron chain transport system.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Mamoci, E., Cavoski, I., Simone, V., et alChemical composition and in vitro activity of plant extracts from Ferula communis and Dittrichia viscosa against postharvest fungi. Molecules 16(3), 2609-2625 (2011).

    2. Monti, M., Pinotti, M., Appendino, G., et alCharacterization of anti-coagulant properties of prenylated coumarin ferulenol. Biochim. Biophys. Acta 1770(10), 1437-1440 (2007).

    3. Bocca, C., Gabriel, L., Bozzo, F., et alMicrotubule-interacting activity and cytotoxicity of the prenylated coumarin ferulenol. Planta Med. 68(12), 1135-1137 (2002).

    4. Lahouel, M., Zini, R., Zellagui, A., et alFerulenol specifically inhibits succinate ubiquinone reductase at the level of the ubiquinone cycle. Biochem. Biophys. Res. Commun. 355(1), 252-257 (2007).