2-(3,4-dimethoxyphenyl)-4H-benzo[h]chromen-4-one

• ChemBase ID: 155044
• Molecular Formular: C21H16O4
• Molecular Mass: 332.34934
• Monoisotopic Mass: 332.10485899
• SMILES: COc1ccc(cc1OC)c1cc(=O)c2ccc3ccccc3c2o1
• Canonical SMILES: COc1ccc(cc1OC)c1cc(=O)c2c(o1)c1ccccc1cc2
• InChI: InChI=1S/C21H16O4/c1-23-18-10-8-14(11-20(18)24-2)19-12-17(22)16-9-7-13-5-3-4-6-15(13)21(16)25-19/h3-12H,1-2H3
• InChIKey: QDZQDIUUJDAORK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(3,4-dimethoxyphenyl)-4H-benzo[h]chromen-4-one
• IUPAC Traditional name: 2-(3,4-dimethoxyphenyl)benzo[h]chromen-4-one
• Synonyms: 2-(3,4-Dimethoxyphenyl)-benzo[h]chromen-4-one; NSC 123391; DiMNF

Database IDs

• CAS Number: 14756-24-2
• MDL Number: MFCD00143008
• PubChem SID: 162249182
• PubChem CID: 276138

CALCULATED PROPERTIES

• Acid pKa: 15.59853
• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 3.6415193
• LogD (pH = 7.4): 3.6415193
• Log P: 3.6415193
• Molar Refractivity: 96.3478 cm^3
• Polarizability: 37.829536 Å^3
• Polar Surface Area: 44.76 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ≥13 mg/mL
• Apperance: white to tan powder

Safety Information

• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 25
• Safety Statements: 45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301
• GHS Precautionary statements: P301 + P310
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C21H16O4

DETAILS

Sigma Aldrich - SML0079

Biochem/physiol Actions
DiMNF is a naphthoflavone derivative, selective aryl hydrocarbon receptor modulator (SAhRM). DiMNF is an AHR ligand that does not induce the expression of AHR dependent genes, such as CYP1A1, but inhibits the expression of cytokine-induced acute phase response proteins such as serum amyloid A and complement C3.