4/'-Hydroxychalcone

• CAT Number: R067204
• CAS Number: 2657-25-2
• Molecular Formula: C15H12O2
• Molecular Weight: 224.259
• Purity: ≥95%
• Synonyms: 2-Benzal-4/’-hydroxyacetophenone;2-Benzylidene-4/’-hydroxyacetophenone;p-Cinnamoylphenol;NSC 242264
• Target: Oxidative Phosphorylation
• Storage: -20°C
• IUPAC Name: (E)-1-(4-hydroxyphenyl)-3-phenylprop-2-en-1-one
• InChI: 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+
• InChIKey: UAHGNXFYLAJDIN-IZZDOVSWSA-N
• SMILES: C1=CC=C(C=C1)C=CC(=O)C2=CC=C(C=C2)O

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. 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. 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 (PMBCs). It also inhibits glutathione reductase (GSH-RD; IC50 = 47.3 μM) in vitro in a reversible and non-competitive manner.

Reference

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).