A chalcone metabolite 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.

4'-hydroxy Chalcone

Item No. 22898

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1-(4-hydroxyphenyl)-3-phenyl-2-propen-1-one
CAS Number
2657-25-2
Synonyms
  • 2-Benzal-4'-hydroxyacetophenone
  • 2-Benzylidene-4'-hydroxyacetophenone
  • p-Cinnamoylphenol
  • NSC 242264
Molecular Formula
C15H12O2
Formula Weight
224.3
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlEthanol: 30 mg/mlEthanol:PBS (pH 7.2) (1:4): 0.2 mg/ml
λmax
228, 322 nm
SMILES
O=C(C1=CC=C(O)C=C1)/C=C/C2=CC=CC=C2
InChi Code
InChI=1S/C15H12O2/c16-14-9-7-13(8-10-14)15(17)11-6-12-4-2-1-3-5-12/h1-11,16H/b11-6+
InChi Key
UAHGNXFYLAJDIN-IZZDOVSWSA-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

    5 g

    $49

    Add

    10 g

    $86

    Add

    25 g

    $178

    Add

    50 g

    $329

    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

    4'-hydroxy Chalcone is a chalcone metabolite with diverse biological activities. It is formed when chalcone is metabolized by the cytochrome (CYP) P450 isoform CYP1A1 or CYP2C6.1 4'-hydroxy Chalcone is estrogenic in MCF-7 cells and is cytotoxic at concentrations higher than 100 nM. It inhibits TNF-α-induced NF-κB signaling and the trypsin-, chymotrypsin-, and caspase-like proteolytic activities of the 26S proteasome in K562 cells in a dose-dependent manner.2 4'-hydroxy Chalcone reduces growth of K562, U937, and Jurkat cancer cell lines in a dose-dependent manner without effecting viability of peripheral blood mononuclear cells (PBMCs). It also inhibits glutathione reductase (GSH-RD; IC50 = 47.3 μM) in vitro in a reversible and non-competitive manner.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kohno, Y., Kitamura, S., Sanoh, S., et al. Metabolism of the α,β-unsaturated ketones, chalcone and trans-4-phenyl-3-buten-2-one, by rat liver microsomes and estrogenic activity of the metabolites. Drug Metab. Dispos. 33(8), 1115-1123 (2005).

    2. Orlikova, B., Tasdemir, D., Golais, F., et al. The aromatic ketone 4'-hydroxychalcone inhibits TNFα-induced NF-κB activation via proteasome inhibition. Biochem. Pharmacol. 82(6), 620-631 (2011).

    3. Zhang, K., Yang, E.-B., Tang, W.-Y., et al. Inhibition of glutathione reductase by plant polyphenols. Biochem. Pharmacol. 54(9), 1047-1053 (1997).