ChemicalBook CAS DataBase List 604-59-1

604-59-1

Name	ALPHA-NAPHTHOFLAVONE
CAS	604-59-1
EINECS(EC#)	210-071-1
Molecular Formula	C19H12O2
MDL Number	MFCD00004985
Molecular Weight	272.3
MOL File	604-59-1.mol

Synonyms

7,8-BENZOFLAVONE ALPHA-NAPHTHOFLAVONE A-NAPHTHOFLAVANONE A-NAPHTHOFLAVONE BENZOFLAVONE NAPHTHOFLAVANONE, A- NAPHTHOFLAVONE, A- 2-b)pyran-4-one,2-phenyl-4h-naphtho( 2-b]pyran-4-one,2-phenyl-4h-naphtho[ 2-phenyl-4h-naphtho(1,2-b)pyran-4-one 2-Phenyl-4H-naphtho[1,2-b]pyran-4-one alpha-naphthylflavone benzo(h)flavone -Naphthoflavone 2-phenylbenzo(h)chromen-4-one alfa-Naphthoflavone ALPHA-NAPHTHOFLAVONE REDOX INDICATOR 1-Naphthoflavone alpha-Naphthoflavone,97% à-naphthoflavone

Chemical Properties

Appearance	yellow powder
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
Stability:	Stable. Incompatible with strong oxidizing agents.
BRN	210862
InChI	InChI=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
InChIKey	VFMMPHCGEFXGIP-UHFFFAOYSA-N
SMILES	C12=C3C(C=CC=C3)=CC=C1C(=O)C=C(C1=CC=CC=C1)O2
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 Data

Symbol(GHS)	GHS07
Signal word	Warning
Hazard statements	H302-H413
Precautionary statements	P264-P270-P273-P301+P312-P330
Hazard Codes	Xi,Xn,C,F
Risk Statements	R68:Possible risk of irreversible effects. R34:Causes burns. R11:Highly Flammable. less more
Safety Statements	S24/25:Avoid contact with skin and eyes . S36/37:Wear suitable protective clothing and gloves . S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) . S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . S16:Keep away from sources of ignition-No smoking . less more
WGK Germany	3
RTECS	QL6250000
F	8
Hazard Note	Irritant
TSCA	Yes
HS Code	29143990

Raw materials And Preparation Products

Hazard Information

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).

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 50

Aromatase

storage

4°C, protect from light

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

Spectrum Detail

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