A triterpenoid 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.

Lupenone

Item No. 35335

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
lup-20(29)-en-3-one
CAS Number
1617-70-5
Synonyms
  • NSC 281807
Molecular Formula
C30H48O
Formula Weight
424.7
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 2 mg/mLDMSO: Slightly solubleEthanol: Slightly soluble
SMILES
C[C@]12[C@@](CC[C@@]3([H])[C@]2(CC[C@]4([H])[C@@]3(CCC(C4(C)C)=O)C)C)([H])[C@]5([H])[C@@](CC1)(CC[C@H]5C(C)=C)C
InChi Code
InChI=1S/C30H48O/c1-19(2)20-11-14-27(5)17-18-29(7)21(25(20)27)9-10-23-28(6)15-13-24(31)26(3,4)22(28)12-16-30(23,29)8/h20-23,25H,1,9-18H2,2-8H3/t20-,21+,22-,23+,25+,27+,28-,29+,30+/m0/s1
InChi Key
GRBHNQFQFHLCHO-BHMAJAPKSA-N
Origin
Plant/Adenophora tetraphylla
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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

    5 mg

    $248

    Add

    10 mg

    $471

    Add

    25 mg

    $1,052

    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

    Lupenone is a triterpenoid that has been found in L. eriocalyx and has diverse biological activities.1,2,3,4 It inhibits HIV-1 reverse transcriptase (IC50 = 2.1 μM).1 Lupenone is active against the W2 and D6 strains of P. falciparum (IC50s = 208.1 and 394.7 ng/ml, respectively).2 It induces melanogenesis in (EC50 = 0.35 µM), and inhibits the growth of, B16 2F2 melanoma cells in vitro (IC50 = 25.4 µM).3 Topical application of lupenone (1 mg/ear) reduces ear edema induced by phorbol 12-myristate 13-acetate (TPA; Item No. 10008014) in mice.4 It also inhibits acetic acid-induced writhing in mice when administered at a dose of 100 mg/kg.2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Akihisa, T., Ogihara, J., Kato, J., et al. Inhibitory effects of triterpenoids and sterols on human immunodeficiency virus-1 reverse transcriptase. Lipids 36(5), 507-512 (2001).

    2. Manguro, L.O.A., Owuor, P.O., and Ochung, A.A. Isolation, characterization and biological activities of phytoconstituents from Lonchocarpus eriocalyx harms leaves. Trends Phytochem. Res. 2(3), 135-146 (2018).

    3. Hata, K., Hori, K., and Takahashi, S. Differentiation- and apoptosis-inducing activities by pentacyclic triterpenes on a mouse melanoma cell line. J. Nat. Prod. 65(5), 645-648 (2002).

    4. Yasukawa, K., Yu, S., Yamanouchi, S., et al. Some lupane-type triterpenes inhibit tumor promotion by 12-O-tetradecanoylphorbol-13-acetate in two-stage carcinogenesis in mouse skin. Phytomedicine 1(4), 309-313 (1995).