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.

LogP

5.003 (est)

CAS DataBase Reference

604-59-1(CAS DataBase Reference)

EPA Substance Registry System

4H-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

F 

8

Hazard Note 

Irritant

TSCA 

Yes

HS Code 

29143990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

α-Naphthoflavone Usage And Synthesis

Chemical Properties

yellow powder

Uses

The 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]

Uses

α-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.

Definition

ChEBI: 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).

Purification Methods

Recrystallise 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

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