3-phenyl-1H-benzo[f]chromen-1-one

• ChemBase ID: 4463
• Molecular Formular: C19H12O2
• Molecular Mass: 272.29738
• Monoisotopic Mass: 272.08372962
• SMILES: o1c2c(c3c(cc2)cccc3)c(=O)cc1c1ccccc1
• Canonical SMILES: O=c1cc(oc2c1c1ccccc1cc2)c1ccccc1
• InChI: InChI=1S/C19H12O2/c20-16-12-18(14-7-2-1-3-8-14)21-17-11-10-13-6-4-5-9-15(13)19(16)17/h1-12H
• InChIKey: OUGIDAPQYNCXRA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-phenyl-1H-benzo[f]chromen-1-one
• IUPAC Traditional name: β-naphthoflavone; β-NF
• Synonyms: 5,6-benzoflavone; beta-NF; 1H-Naphtho(2,1-b)pyran-1-one, 3-phenyl-; 1H-Naphtho[2,1-b]pyran-1-one, 3-phenyl-; 3-Phenyl-1H-benzo[f]chromen-1-one; 3-Phenyl-1H-naphtho(2,1-b)pyran-1-one; 3-Phenyl-1H-naphtho[2,1-b]pyran-1-one; 3-Phenyl-benzo[f]chromen-1-one; 3-phenyl-1H-benzo[f]chromen-1-one (ACD/Name 4.0); 5,6 Benzoflavone; BIDD:ER0570; BNF; N3633_SIGMA; WLN: T B666 CV FOJ ER; {1H-Naphtho[2,} 1-b\]pyran-1-one, 3-phenyl-; {3-Phenyl-1H-naphtho[2,} 1-b\]pyran-1-one; beta-Naphthoflavone; beta-Naphthoflavone; β-Naphthoflavone; beta-Naphthoflavone; β-NAPHTHOFLAVONE; 5,6-苯并黄酮; β-萘黄酮; β-萘基黄酮

Database IDs

• CAS Number: 6051-87-2
• EC Number: 227-958-4
• MDL Number: MFCD00004986
• Beilstein Number: 18991
• PubChem SID: 24886080; 24897657; 160967895; 99443278
• PubChem CID: 2361
• CHEMBL: 26260
• Chemspider ID: 2271
• DrugBank ID: DB06732
• Wikipedia Title: Beta-Naphthoflavone

CALCULATED PROPERTIES

• Acid pKa: 15.421028
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 3.956862
• LogD (pH = 7.4): 3.9568617
• Log P: 3.956862
• Molar Refractivity: 83.4214 cm^3
• Polarizability: 32.867867 Å^3
• Polar Surface Area: 26.3 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: yellow to tan
• Melting Point: 162-166°C; 164-166 °C; 164-166 °C(lit.); 164-166°C

Safety Information

• Storage Condition: 2-8°C
• Storage Warning: Irritant
• RTECS: QL6200000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: rat ... Gabra2(29706)

Product Information

• Purity: 92-95%; 98+%
• Grade: purum
• Empirical Formula (Hill Notation): C19H12O2

DETAILS

MP Biomedicals - 02195339

Yellow/tan crystals
Purity: 92-95%
Inhibitor of aryl hydrocarbon hydroxylase.

MP Biomedicals - 05216787

MP Biomedicals Rare Chemical collection

DrugBank - DB06732

• Drug Groups: experimental
• Description: beta-Naphthoflavone, also known as 5,6-benzoflavone, is a potent agonist of the aryl hydrocarbon receptor and as such is an inducer of such detoxification enzymes as cytochromes P450 (CYPs) and uridine 5'-diphospho-glucuronosyltransferases (UGTs). β-Naphthoflavone is a putative chemopreventive agent.
• References: Chlouchi A, Girard C, Bonet A, Viollon-Abadie C, Heyd B, Mantion G, Martin H, Richert L: Effect of chrysin and natural coumarins on UGT1A1 and 1A6 activities in rat and human hepatocytes in primary culture. Planta Med. 2007 Jul;73(8):742-7. Epub 2007 Jun 28. [Pubmed] ; Izzotti A, Bagnasco M, Cartiglia C, Longobardi M, Camoirano A, Tampa E, Lubet RA, De Flora S: Modulation of multigene expression and proteome profiles by chemopreventive agents. Mutat Res. 2005 Dec 11;591(1-2):212-23. Epub 2005 Aug 3. [Pubmed]
• External Links: Wikipedia

Sigma Aldrich - N3633

包装
1, 5 g in poly bottle

REFERENCES

• Cancer Res. , 32 : 731, 1329 (1972).
• Chlouchi A, Girard C, Bonet A, Viollon-Abadie C, Heyd B, Mantion G, Martin H, Richert L: Effect of chrysin and natural coumarins on UGT1A1 and 1A6 activities in rat and human hepatocytes in primary culture. Planta Med. 2007 Jul;73(8):742-7. Epub 2007 Jun 28. Pubmed
• Izzotti A, Bagnasco M, Cartiglia C, Longobardi M, Camoirano A, Tampa E, Lubet RA, De Flora S: Modulation of multigene expression and proteome profiles by chemopreventive agents. Mutat Res. 2005 Dec 11;591(1-2):212-23. Epub 2005 Aug 3. Pubmed