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α-Naphthoflavone

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Products Intro: Product Name:α-Naphthoflavone
CAS:604-59-1
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  • α-Naphthoflavone
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α-Naphthoflavone Basic information
Product Name:α-Naphthoflavone
Synonyms:7,8-BENZOFLAVONE;ALPHA-NAPHTHOFLAVONE;A-NAPHTHOFLAVANONE;A-NAPHTHOFLAVONE;BENZOFLAVONE;NAPHTHOFLAVANONE, A-;NAPHTHOFLAVONE, A-;2-b)pyran-4-one,2-phenyl-4h-naphtho(
CAS:604-59-1
MF:C19H12O2
MW:272.3
EINECS:210-071-1
Product Categories:Flavones;Analytical Reagents;Aryl Hydrocarbon Receptor Antagonist;Cancer Research;Chemopreventive Agents;Redox Indicators;Analytical/Chromatography;Benzopyrans;Bioactive Small Molecules;Building Blocks;Cell Biology;Chemical Synthesis;Heterocyclic Building Blocks;Indicators;N;Titration;Industrial/Fine Chemicals
Mol File:604-59-1.mol
α-Naphthoflavone Structure
α-Naphthoflavone Chemical Properties
Melting point 153-157 °C (lit.)
Boiling point 375.35°C (rough estimate)
density 1.1382 (rough estimate)
refractive index 1.5510 (estimate)
storage temp. 2-8°C
solubility Chloroform (Slightly), Ethyl Acetate (Slightly)
form Crystalline Powder or Crystals
color yellow
BRN 210862
Stability:Stable. Incompatible with strong oxidizing agents.
InChIInChI=1S/C19H12O2/c20-17-12-18(14-7-2-1-3-8-14)21-19-15-9-5-4-6-13(15)10-11-16(17)19/h1-12H
InChIKeyVFMMPHCGEFXGIP-UHFFFAOYSA-N
SMILESC12=C3C(C=CC=C3)=CC=C1C(=O)C=C(C1=CC=CC=C1)O2
LogP5.003 (est)
CAS DataBase Reference604-59-1(CAS DataBase Reference)
EPA Substance Registry System4H-Naphtho[1,2-b]pyran-4-one, 2-phenyl- (604-59-1)
Safety Information
Hazard Codes Xi,Xn,C,F
Risk Statements 68-34-11
Safety Statements 24/25-36/37-45-36/37/39-26-16
WGK Germany 3
RTECS QL6250000
8
Hazard Note Irritant
TSCA TSCA listed
HS Code 29143990
MSDS Information
ProviderLanguage
SigmaAldrich English
ACROS English
ALFA English
α-Naphthoflavone Usage And Synthesis
Chemical Propertiesyellow powder
UsesThe aryl hydrocarbon receptor (AhR) is a ligand-activated transcription factor that promotes the expression of phase I and II xenobiotic chemical metabolizing enzyme genes, including the cytochrome P450 (CYP) isoforms CYP1A1 and CYP1A2. α-Naphthoflavone is a flavone that modulates xenobiotic metabolism at several points. It antagonizes AhR, blocking the expression of phase I and II genes at nanomolar concentrations, although it can agonize AhR at higher concentrations (10 μM). α-Naphthoflavone inhibits CYP19 (aromatase), CYP1A1, CYP1A2, and CYP1B1 (IC50s = 500, 60, 6, and 5 nM, respectively), whereas it activates CYP3A4 (Kd = 7.4 μM). Dietary α-naphthoflavone can contribute to carcinogenesis in the presence of synthetic estrogens.[Cayman Chemical]
Usesα-Naphthylflavone is a flavenoid compound that acts on μ-opioid receptors in the treatment of pain. Also acts as a non-steroidal aromatase inhibitor used in breast cancer therapy.
DefinitionChEBI: An extended flavonoid resulting from the formal fusion of a benzene ring with the h side of flavone. A synthetic compound, it is an inhibitor of aromatase (EC 1.14.14.14).
in vivo

Alpha-Naphthoflavone (80, 160 mg/kg/day, gavage for 4 weeks) has protective effects on NAFLD mice induced by high-fat diet (HFD)[4].

Animal Model:HFD-induced mice model[4]
Dosage:80, 160 mg/kg
Administration:i.g.
Result:Decreased the levels of AST, TG and TC.
IC 50Aromatase
Purification MethodsRecrystallise the flavone from EtOH or aqueous EtOH. [IR: Cramer & Windel Chem Ber 89 354 1956, UV Pillon & Massicot Bull Soc Chim Fr 26 1954, Smith J Chem Soc 542
α-Naphthoflavone Preparation Products And Raw materials
Raw materialsFLAVONE-->FLAVANONE-->trans-Chalcone
Tag:α-Naphthoflavone(604-59-1) Related Product Information
3,5-DIHYDROXY-4'-METHOXYSTILBENE 3-O-BETA-D-GLUCOSIDE PONCIRIN RHAPONTIN MOSLOFLAVONE Quercetin-7-O-β-D-glucopyranoside GARDENIN B Naringenin Fluconazole Dextromethorphan α-Naphthoflavone A-NAPHTHOFLAVONOL 4'-HYDROXY-ALPHA-NAPHTHOFLAVONE 2'-HYDROXY-ALPHA-NAPHTHOFLAVONE 4'-METHOXY-ALPHA-NAPHTHOFLAVONE 2'-METHOXY-ALPHA-NAPHTHOFLAVONE 3',4'-DIHYDROXY-ALPHA-NAPHTHOFLAVONE 3'-HYDROXY-A-NAPHTHOFLAVONE 3',4'-DIMETHOXY-ALPHA-NAPHTHOFLAVONE

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