3-(3,4-dihydroxyphenyl)-7-hydroxy-4H-chromen-4-one

• ChemBase ID: 156804
• Molecular Formular: C15H10O5
• Molecular Mass: 270.2369
• Monoisotopic Mass: 270.05282342
• SMILES: c1cc(c(cc1c1coc2cc(ccc2c1=O)O)O)O
• Canonical SMILES: Oc1ccc2c(c1)occ(c2=O)c1ccc(c(c1)O)O
• InChI: InChI=1S/C15H10O5/c16-9-2-3-10-14(6-9)20-7-11(15(10)19)8-1-4-12(17)13(18)5-8/h1-7,16-18H
• InChIKey: DDKGKOOLFLYZDL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(3,4-dihydroxyphenyl)-7-hydroxy-4H-chromen-4-one
• IUPAC Traditional name: 3',4',7-trihydroxyisoflavone
• Synonyms: 3',4',7-Trihydroxyisoflavone; 3′,4′,7-Trihydroxyisoflavone; 3-(3,4-Dihydroxyphenyl)-7-hydroxy-4H-1-benzopyran-4-one; 3',4',7-Trihydroxyisoflavone; 3',4',7-三羟基异黄酮

Database IDs

• CAS Number: 485-63-2
• MDL Number: MFCD00143002
• Beilstein Number: 251800
• PubChem SID: 162250941
• PubChem CID: 5284648

CALCULATED PROPERTIES

• Acid pKa: 6.475111
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 2.383449
• LogD (pH = 7.4): 1.4578047
• Log P: 2.4268725
• Molar Refractivity: 71.6829 cm^3
• Polarizability: 27.107475 Å^3
• Polar Surface Area: 86.99 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMF; Ethanol; Methanol
• Apperance: Off-White Solid
• Melting Point: 278-281°C dec.; 280-282°C

Safety Information

• Storage Condition: -20°C Freezer
• Storage Warning: Store in Freezer
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-37
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥97.0% (TLC); 97%
• Empirical Formula (Hill Notation): C15H10O5

DETAILS

Sigma Aldrich - 91953

General description
Major metabolite of daidzein in bacteria.1 Inhibits EGF-induced neoplastic transformation and proliferation of cultured mouse epidermal cells, acting through cyclin-dependent kinases and phosphatidylinositol 3-kinase (PI3K) inhibition.2

Toronto Research Chemicals - T795200

Inhibits β-galactosidase enzyme.

REFERENCES

• Biosci. Biotechnol. Biochem., 57(1)
• 107 (1993)