A natural prenylated chalcone
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.

Xanthohumol

Item No. 15399

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2E)-1-[2,4-dihydroxy-6-methoxy-3-(3-methyl-2-buten-1-yl)phenyl]-3-(4-hydroxyphenyl)-2-propen-1-one
CAS Number
6754-58-1
Molecular Formula
C21H22O5
Formula Weight
354.4
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 2 mg/mlDMSO: 2 mg/mlDMSO:PBS(pH 7.2) (1:3): 0.25 mg/mlEthanol: 2 mg/ml
λmax
348, 368 nm
SMILES
OC1=C(C(/C=C/C2=CC=C(O)C=C2)=O)C(OC)=CC(O)=C1C/C=C(C)/C
InChi Code
InChI=1S/C21H22O5/c1-13(2)4-10-16-18(24)12-19(26-3)20(21(16)25)17(23)11-7-14-5-8-15(22)9-6-14/h4-9,11-12,22,24-25H,10H2,1-3H3/b11-7+
InChi Key
ORXQGKIUCDPEAJ-YRNVUSSQSA-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.

Download most recent Certificate of Analysis for this product

    1 mg

    $28

    Add

    5 mg

    $83

    Add

    10 mg

    $138

    Add

    25 mg

    $241

    Add
    Kinase Resource Center
    Discover Products & Resources for Kinase Research
    • Kinase inhibitors, screening libraries, assay kits, & more
    • Tools to study kinase signaling pathways:
      • Growth factor signaling
      • PI3K/Akt/mTOR
      • MAPKs (ERK, p38, & JNK)
      • JAK/STAT signaling
    • Articles, resources, & advice
    EXPLORE NOW
    Product Description

    Xanthohumol is a natural prenylated chalcone isolated from the hop plant, H. lupulus. Xanthohumol and its metabolites induce protective detoxification enzymes, at least in part via the nuclear factor erythroid-2-related factor 2 pathway.1,2 It inhibits phosphoinositide-dependent kinase 1 (IC50 = 6.6 μM) but not PKC in an in vitro assay.3 Xanthohumol also can have anti-inflammatory, antioxidant, anti-carcinogenic, and osteogenic effects.4,5,6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Krajka-Kuzniak, V., Paluszczak, J., and Baer-Dubowska, W. Xanthohumol induces phase II enzymes via Nrf2 in human hepatocytes in vitro. Toxicol. In Vitro 27(1), 149-156 (2013).

    2. Dietz, B.M., and Bolton, J.L. Biological reactive intermediates (BRIs) formed from botanical dietary supplements. Chem. Biol. Interact. 192(1-2), 72-80 (2011).

    3. Lauro, G., Masullo, M., Piacente, S., et al. Inverse virtual screening allows the discovery of the biological activity of natural compounds. Bioorg. Med. Chem. 20(11), 3596-3602 (2012).

    4. Costa, R., Negrao, R., Valente, I., et al. Xanthohumol modulates inflammation, oxidative stress, and angiogenesis in type 1 diabetic rat skin wound healing. J. Nat. Prod. 76(11), 2047-2053 (2013).

    5. Venè, R., Benelli, R., Minghelli, S., et al. Xanthohumol impairs human prostate cancer cell growth and invasion and diminishes the incidence and progression of advanced tumors in TRAMP mice. Mol. Med. 18(1), 1292-1302 (2012).

    6. Schilling, T., Ebert, R., Raaijmakers, N., et al. Effects of phytoestrogens and other plant-derived compounds on mesenchymal stem cells, bone maintenance and regeneration. J. Steroid Biochem. Mol. Biol. 139, 252-261 (2014).