An anti-inflammatory compound that activates Nrf2/ARE signaling
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.

CDDO

Item No. 81035

Technical Information
Formal Name
2-cyano-3,12-dioxo-oleana-1,9(11)-dien-28-oic acid
CAS Number
218600-44-3
Synonyms
  • Bardoxolone
  • RTA 401
Molecular Formula
C31H41NO4
Formula Weight
Purity
≥95%
A crystalline solid
DMF: 5 mg/mlDMSO: 5 mg/mlEthanol: 5 mg/mlEthanol:PBS(pH 7.2) (1:1): 0.5 mg/ml
λmax
240 nm
SMILES
N#CC1=C[C@@]2(C)[C@](CC[C@]([C@@]3(C)[C@@]4([H])C5[C@@](CCC(C)(C)C5)(C(O)=O)CC3)(C)C2=CC4=O)([H])C(C)(C)C1=O
InChi Code
InChI=1S/C31H41NO4/c1-26(2)10-12-31(25(35)36)13-11-30(7)23(19(31)16-26)20(33)14-22-28(5)15-18(17-32)24(34)27(3,4)21(28)8-9-29(22,30)6/h14-15,19,21,23H,8-13,16H2,1-7H3,(H,35,36)/t19?,21-,23-,28-,29+,30+,31?/m0/s1
InChi Key
TXGZJQLMVSIZEI-RPCUOREFSA-N
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

    CDDO is a synthetic oleanane triterpenoid that blocks the cellular synthesis of inducible nitric oxide synthase and inducible COX-2 in INF-γ-activated mouse macrophages with an IC50 value of 0.4 nM.1 By suppressing reactive oxygen and nitrogen species (ROS/RNS) formation, it promotes the cellular control of ROS/RNS levels that would lead to DNA damage associated with tumorigenesis.2 In various cancer cell lines, CDDO has been shown to specifically inhibit proliferation and induce apoptosis.2 Mechanism studies revealed that CDDO is a ligand for peroxisome proliferator-activated receptor γ, and also that it induces genes regulated by Nrf2, including heme oxygenase-1 and eotaxin-1, which play a role in antioxidant response element signaling activity.3,4,5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Honda, T., Rounds, B.V., Gribble, G.W., et alDesign and synthesis of 2-cyano-3,12-dioxoolean-1,9-dien-28-oic acid, a novel and highly active inhibitor of nitric oxide production in mouse macrophages. Bioorg. Med. Chem. Lett. 8, 2711-2714 (1998).

    2. Suh, N., Wang, Y., Honda, T., et alA novel synthetic oleanane triterpenoid, 2-cyano-3,12-dioxoolean-1,9-dien-28-oic acid, with potent differentiating, antiproliferative, and anti-inflammatory activity. Cancer Res. 59, 336-341 (1999).

    3. Ferguson, H.E., Kulkarni, A., Lehmann, G.M., et alElectrophilic peroxisome proliferator-activated receptor-γ ligands have potent antifibrotic effects in human lung fibroblasts. Am. J. Respir. Cell Mol. Biol. 41, 722-730 (2009).

    4. Liby, K., Hock, T., Yore, M.M., et alThe synthetic triterpenoids, CDDO and CDDO-imidazolide, are potent inducers of heme oxygenase-1 and Nrf2/ARE signaling. Cancer Res. 65(11), 4789-4798 (2005).

    5. Fourtounis, J., Wang, I.M., Mathieu, M.C., et alGene expression profiling following NRF2 and KEAP1 siRNA knockdown in human lung fibroblasts identifies CCL11/Eotaxin-1 as a novel NRF2 regulated gene. Respir. Res. 13(1), (2012).