CAS 315204-48-9

4H-1-Benzopyran-4-one, 5,7-dihydroxy-3-(4-hydroxyphenyl-3,5-d2)-

Description:

4H-1-Benzopyran-4-one, 5,7-dihydroxy-3-(4-hydroxyphenyl-3,5-d2) is a chemical compound characterized by its complex structure, which includes a benzopyran core with multiple hydroxyl groups and a deuterated phenyl substituent. This compound belongs to the class of flavonoids, which are known for their diverse biological activities, including antioxidant, anti-inflammatory, and potential anticancer properties. The presence of hydroxyl groups enhances its reactivity and solubility in polar solvents, while the deuterated phenyl group may influence its isotopic labeling in studies. The compound's molecular structure contributes to its potential applications in pharmaceuticals and nutraceuticals. Additionally, its unique isotopic composition can be useful in tracing metabolic pathways in biological research. Overall, this compound exemplifies the intricate relationship between molecular structure and biological function, making it a subject of interest in both synthetic and natural product chemistry.

Formula: C₁₅H₈D₂O₅

InChI: InChI=1S/C15H10O5/c16-9-3-1-8(2-4-9)11-7-20-13-6-10(17)5-12(18)14(13)15(11)19/h1-7,16-18H/i3D,4D

InChI key: InChIKey=TZBJGXHYKVUXJN-NMQOAUCRSA-N

SMILES: O=C1C=2C(OC=C1C3=CC(=C(O)C(=C3)[2H])[2H])=CC(O)=CC2O

Synonyms:

• 4H-1-Benzopyran-4-one, 5,7-dihydroxy-3-(4-hydroxyphenyl-3,5-d2)-

Genistein-2’,6’-d2

Controlled Product

CAS: 315204-48-9

Applications Exhibits specific inhibitory activity against tyrosine kinases,including autophosphorylation of epidermal growth factor receptor kinase (IC50 - 2.6uM). Also inhibits other protein kinases through competitive inhibition of ATP. Inhibits tumor cell proliferation and induces tumor cell differentiation. Produces cell-cycle arrest and apoptosis in Jurat T-leukemia cells. However, it prevents anti-CD3 monoclonal antibody-induced thymic apoptosis. Genistein also inhibits topoisomerase II activity in vitro. Genistein has also been shown to inhibit the action of GABA on recombinant GABAA receptors2. uv(max)ethanol: 262.5 nm (e= 138). moderately sol. in hot alcohol
References Akiyama, T., et al.: J. Biol. Chem., 262, 5592 (1987), O'Dell, T.J., et al.: Nature, 353, 588 (1991), Aharonovits, O., et al.: Biochim Biophys. Acta, 1112, 181 (1992), Platanias, L.C., et al.: J. Biol. Chem., 267, 24053 (1992), Yoshida, H., et al.: Biochim. Biophys. Acta, 1137, 321 (1992), Uckun, F.M., et al.: Science, 267, 886 (1995)Merck Index 12th ed. 43952. Huang, R.Q.; Fang, M.J.; Dillon, G.H., Mol. Brain Res. 67: 177-183 (1999)

Formula: C₁₅₂H₂H₈O₅

Color and Shape: Neat

Molecular weight: 272.25

Ref: TR-G350005