5,7-dihydroxy-2-(4-methoxyphenyl)-4H-chromen-4-one

• ChemBase ID: 105757
• Molecular Formular: C16H12O5
• Molecular Mass: 284.26348
• Monoisotopic Mass: 284.06847348
• SMILES: COc1ccc(cc1)c1cc(=O)c2c(o1)cc(O)cc2O
• Canonical SMILES: COc1ccc(cc1)c1cc(=O)c2c(o1)cc(cc2O)O
• InChI: InChI=1S/C16H12O5/c1-20-11-4-2-9(3-5-11)14-8-13(19)16-12(18)6-10(17)7-15(16)21-14/h2-8,17-18H,1H3
• InChIKey: DANYIYRPLHHOCZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5,7-dihydroxy-2-(4-methoxyphenyl)-4H-chromen-4-one
• IUPAC Traditional name: acacetin
• Synonyms: 5,7-DIHYDROXY-4'-METHOXY FLAVONE; 5,7-dihydroxy-4′-methoxyflavone; 4'-methoxy-5,7-dihydroxyflavone; Linarigenin; Acacetine; Buddleoflavonol; Linarisenin; 4'-Methoxyapigenin; Apigenin 4'-methyl ether; 5,7-Dioxy-4'-methoxyflavone; 5,7-Dihydroxy-2-(4-methoxyphenyl)-4H-chromen-4-one; 5,7-Dihydroxy-4'-methoxyflavone; ACACETIN; Acacetin; 2-(4-Methoxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-one; 4'-O-Methylapigenin; LY 064233; NSC 76061

Database IDs

• CAS Number: 480-44-4
• EC Number: 207-552-3
• MDL Number: MFCD00016936
• Beilstein Number: 277879
• PubChem SID: 162092578
• PubChem CID: 5280442
• CHEBI ID: 15335
• CHEMBL: 243664
• Chemspider ID: 4444099
• Wikipedia Title: Acacetin

CALCULATED PROPERTIES

• Acid pKa: 6.577781
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 2.8179076
• LogD (pH = 7.4): 1.9315174
• Log P: 2.8525832
• Molar Refractivity: 77.3962 cm^3
• Polarizability: 29.011778 Å^3
• Polar Surface Area: 75.99 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Pale Yellow Solid; Yellow powder
• Melting Point: 260-265 °C(lit.); 262-264°C (dec.); 263°C

Safety Information

• Storage Condition: -20°C Freezer; Room Temperature (15-30°C)
• RTECS: DJ3002000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

DETAILS

MP Biomedicals - 02193972

Possesses antioxidant properties and an inhibitor of rat liver glutathione S-transferase.

MP Biomedicals - 05212415

MP Biomedicals Rare Chemical collection

Sigma Aldrich - A8206

Biochem/physiol Actions
A flavonoid derivative possessing antioxidant properties.2 Induces cell cycle arrest and apoptosis in a time- and dose-dependent manner in several cancer cell lines in vitro.
Flavonoid with anti-peroxidative and anti-inflammatory properties. Used in traditional Chinese medicine. It has been recognized as an antiproliferative agent on cancer cell lines by inducing apoptosis and blocking cell cycle progression in the G1 phase.1

Toronto Research Chemicals - A123580

VEGF expression inhibitor and tumor angiogenesis. A flavonoid with antiaggregatory activity in human blood.

REFERENCES

• Zhang, K. and Das, N.P., Biochem. Pharmacol. , 47 : 2063 (1994).
• Liu, L. et al.: Biochem. Bioph. Res. Co. 413, 299 (2011)
• Bojic, M. et al.: Nutrition J. 10, 73 (2011)