2-(3,4-dimethoxyphenyl)-4H-chromen-4-one

• ChemBase ID: 154775
• Molecular Formular: C17H14O4
• Molecular Mass: 282.29066
• Monoisotopic Mass: 282.08920893
• SMILES: COc1ccc(cc1OC)c1cc(=O)c2ccccc2o1
• Canonical SMILES: COc1cc(ccc1OC)c1cc(=O)c2c(o1)cccc2
• InChI: InChI=1S/C17H14O4/c1-19-15-8-7-11(9-17(15)20-2)16-10-13(18)12-5-3-4-6-14(12)21-16/h3-10H,1-2H3
• InChIKey: ZGHORMOOTZTQFL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(3,4-dimethoxyphenyl)-4H-chromen-4-one
• IUPAC Traditional name: 2-(3,4-dimethoxyphenyl)chromen-4-one
• Synonyms: 3',4'-Dimethoxyflavone; 2-(3,4-Dimethoxyphenyl)chromen-4-one; 3′,4′-DMF; 3′,4′-Dimethoxyflavone; 3',4'-二甲氧基黄酮

Database IDs

• CAS Number: 4143-62-8
• MDL Number: MFCD00143009
• Beilstein Number: 236749
• PubChem SID: 162248913
• PubChem CID: 688674

CALCULATED PROPERTIES

• Acid pKa: 15.675329
• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 2.6520426
• LogD (pH = 7.4): 2.6520426
• Log P: 2.6520426
• Molar Refractivity: 79.8976 cm^3
• Polarizability: 30.30054 Å^3
• Polar Surface Area: 44.76 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ≥20 mg/mL
• Apperance: white to off-white powder
• Melting Point: 154-155°C

Safety Information

• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 25
• Safety Statements: 45
• TSCA Listed: 否
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301
• GHS Precautionary statements: P301 + P310
• Storage Temperature: room temp

Product Information

• Purity: ≥98% (HPLC); 97%
• Empirical Formula (Hill Notation): C17H14O4
• Classification: Derivatives & analogs of Natural Compounds

DETAILS

Sigma Aldrich - D6571

Biochem/physiol Actions
3′,4′-dimethoxyflavone is a competitive antagonist of the AhR that inhibits AhR-mediated induction of CYP1A1, and also displays antiestrogen activity in breast tumor cell lines. The compound blocks transformation of the cytosolic AhR complex, and formation of nuclear AhR complexes.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. D6571.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.