A germacranolide sesquiterpene lactone with diverse biological activities
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.

Cnicin

Item No. 38969

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(3R)-3,4-dihydroxy-2-methylene-butanoic acid, (3aR,4S,6E,10Z,11aR)-2,3,3a,4,5,8,9,11a-octahydro-10-(hydroxymethyl)-6-methyl-3-methylene-2-oxocyclodeca[b]furan-4-yl ester
CAS Number
24394-09-0
Synonyms
  • (+)-Cnicin
Molecular Formula
C20H26O7
Formula Weight
378.4
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Acetonitrile: SolubleMethanol: Soluble
SMILES
O=C(C1=C)O[C@@]2([H])[C@@]1([H])[C@@H](OC(C([C@@H](O)CO)=C)=O)C/C(C)=C/CC/C(CO)=C/2
InChi Code
InChI=1S/C20H26O7/c1-11-5-4-6-14(9-21)8-17-18(13(3)20(25)27-17)16(7-11)26-19(24)12(2)15(23)10-22/h5,8,15-18,21-23H,2-4,6-7,9-10H2,1H3/b11-5+,14-8-/t15-,16-,17+,18+/m0/s1
InChi Key
ZTDFZLVUIVPZDU-QGNHJMHWSA-N
Origin
Plant/Centaurea maculosa
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

    $50

    Add

    1 mg

    $95

    Add

    5 mg

    $372

    Add

    10 mg

    $545

    Add
    Lipid Resource Center
    Discover Products & Resources for Lipid Research
    • High-purity lipid standards
    • Lipid roles in biology
    • Lipids in health & disease
    • Lipids for pharmaceutical development
    • Protocols, advice, & resources
    EXPLORE NOW
    Product Description

    Cnicin is a germacranolide sesquiterpene lactone that has been found in Centaurea and has diverse biological activities.1,2,3 It irreversibly inhibits the UDP-N-acetylglucosamine (UDP-GlcNAc) 1-carboxyvinyltransferase MurA (IC50s = 16.7 and 10.3 for the E. coli and P. aeruginosa enzymes, respectively) and is active against B. cereus and M. flavus (MICs = 1.25 and 5 µg/ml, respectively).1,2 Cnicin inhibits the growth of MCF-7 breast and OVCAR-3 ovarian cancer cells (GI50s = 37.8 and 37.4 µM, respectively).2 It reduces snake venom-induced paw edema in rats when administered at doses ranging from 2.5 to 10 mg/kg.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Bachelier, A., Mayer, R., and Klein, C.D. Sesquiterpene lactones are potent and irreversible inhibitors of the antibacterial target enzyme MurA. Bioorg. Med. Chem. Lett. 16(21), 5605-5609 (2006).

    2. Saroglou, V., Karioti, A., Demetzos, C., et al. Sesquiterpene lactones from Centaurea spinosa and their antibacterial and cytotoxic activities. J. Nat. Prod. 68(9), 1404-1407 (2005).

    3. Demiroz, T., Albayrak, G., Nalbantsoy, A., et al. Anti-inflammatory properties of Centaurea calolepis Boiss. and cnicin against Macrovipera lebetina obtusa (Dwigubsky, 1832) and Montivipera xanthina (Gray, 1849) venoms in rat. Toxicon 152, 37-42 (2018).