α-Naphthoflavone

Synonym(s):7,8-Benzoflavone;alpha-Naphthoflavone

CAS NO.：604-59-1
Empirical Formula: C19H12O2
Molecular Weight: 272.3
MDL number: MFCD00004985
EINECS: 210-071-1
SAFETY DATA SHEET (SDS)
Update Date: 2023-11-14 14:35:52

What is α-Naphthoflavone?

Chemical properties

yellow powder

The Uses of α-Naphthoflavone

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]

The Uses of α-Naphthoflavone

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.

What are the applications of Application

α-Naphthoflavone is an aryl hydrocarbon receptor inhibitor

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

Properties of α-Naphthoflavone

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.
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 for α-Naphthoflavone

Signal word	Warning
Pictogram(s)	Exclamation Mark Irritant GHS07
GHS Hazard Statements	H302:Acute toxicity,oral H413:Hazardous to the aquatic environment, long-term hazard
Precautionary Statement Codes	P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P270:Do not eat, drink or smoke when using this product. P273:Avoid release to the environment. P330:Rinse mouth. P301+P312:IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.