604-59-1

Basic information

• Product Name: α-Naphthoflavone
• Synonyms: ALPHA-NAPHTHOFLAVONE;A-NAPHTHOFLAVANONE;A-NAPHTHOFLAVONE;7,8-BENZOFLAVONE;BENZOFLAVONE;NAPHTHOFLAVANONE, A-;NAPHTHOFLAVONE, A-;2-b)pyran-4-one,2-phenyl-4h-naphtho(
• CAS NO: 604-59-1
• Molecular Formula: C₁₉H₁₂O₂
• Molecular Weight: 272.3
• EINECS: 210-071-1
• Product Categories: Industrial/Fine Chemicals;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
• Mol File: 604-59-1.mol
• Article Data: 14

Chemical Properties

• Melting Point: 153-157 °C(lit.)
• Boiling Point: 375.35°C (rough estimate)
• Flash Point: 215.8 °C
• Appearance: yellow/Crystalline Powder or Crystals
• Density: 1.1382 (rough estimate)
• Vapor Pressure: 1.12E-08mmHg at 25°C
• Refractive Index: 1.5510 (estimate)
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• Stability: Stable. Incompatible with strong oxidizing agents.
• BRN: 210862
• CAS DataBase Reference: α-Naphthoflavone(CAS DataBase Reference)
• NIST Chemistry Reference: α-Naphthoflavone(604-59-1)
• EPA Substance Registry System: α-Naphthoflavone(604-59-1)

Safety Data

• Hazard Codes: Xi,Xn,C,F
• Statements: 68-34-11
• Safety Statements: 24/25-36/37-45-36/37/39-26-16
• WGK Germany: 3
• RTECS: QL6250000
• F: 8
• TSCA: Yes
• Hazardous Substances Data: 604-59-1(Hazardous Substances Data)

Usage

Description

α-Naphthoflavone is an extended flavonoid resulting from the formal fusion of a benzene ring with the h side of flavone. It is a synthetic compound that exhibits various biological activities, including modulation of xenobiotic metabolism and interaction with specific receptors.

Uses

Used in Xenobiotic Metabolism Regulation:
α-Naphthoflavone is used as a modulator of xenobiotic metabolism for its ability to antagonize the aryl hydrocarbon receptor (AhR) at nanomolar concentrations, thereby blocking the expression of phase I and II genes involved in xenobiotic chemical metabolizing enzyme genes, such as CYP1A1 and CYP1A2.
Used in Aromatase Inhibition:
α-Naphthoflavone is used as a non-steroidal aromatase inhibitor for its role in breast cancer therapy, where it inhibits the enzyme CYP19, which is involved in the synthesis of estrogen.
Used in Pain Management:
α-Naphthoflavone is used as an agonist of μ-opioid receptors in the treatment of pain, providing an alternative approach to pain management.
Used in Drug Development:
α-Naphthoflavone is used as a chemical probe in drug development due to its inhibitory effects on various cytochrome P450 isoforms, such as CYP1A1, CYP1A2, CYP1B1, and its activating effect on CYP3A4.
Chemical Properties:
α-Naphthoflavone is a yellow powder with a molecular structure that allows it to interact with specific biological targets and modulate various cellular processes.

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

InChI:InChI=1/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

Upstream product

• 711-79-5 1-hydroxy-2-acetonaphthone 
• 93-97-0 benzoic acid anhydride 
• 90-15-3 α-naphthol 
• 63888-21-1 benzyl 3-phenyl-2-propynoate 
• 100-52-7 benzaldehyde 
• 135-19-3 β-naphthol 
• 1621629-28-4 C₁₉H₁₄O₃ 
• 125574-15-4 (E)-1-(1-hydroxynaphthalen-2-yl)-3-phenylprop-2-en-1-one 
• 108-86-1 bromobenzene 
• 201230-82-2 carbon monoxide 
• 536-74-3 phenylacetylene 
• 574-96-9 1-hydroxy-2-naphthaldehyde 
• 129986-83-0 (E)-1-(1-Methoxymethoxy-naphthalen-2-yl)-3-phenyl-prop-2-en-1-ol 
• 129986-92-1 (E)-1-(1-Methoxymethoxy-naphthalen-2-yl)-3-phenyl-propenone 

Downstream Products

• 86126-12-7 C₁₉H₁₄O₄ 
• 98166-67-7 UCCF 355 
• 1201199-67-8 C₁₉H₁₄⁽²⁾H₂O₂ 
• 1201199-66-7 C₁₉H₁₄⁽²⁾H₂O₂ 
• 131720-55-3 2-phenyl-4H-benzo[h]chromene 
• 22812-50-6 3-hydroxy-2-phenyl-4H-benzo[h]chromen-4-one 
• 65-85-0 benzoic acid 
• 139448-83-2 1-Phenyl-1-(phenylthio)-3-(2-naphthyl)-prop-1-ene-3-thione 
• 103402-93-3 2-Hydroxy-3,4-benzo-ω-phenyl-ω-<2,7-dibrom-fluorenyliden-(9)>-propiophenon 
• 103267-01-2 2-Hydroxy-3,4-benzo-ω-phenyl-ω--propiophenon 
• 14882-98-5 2-phenyl-4H-benzo[h]chromene-4-thione 

Relevant articles and documents

An efficient tandem synthesis of chromones from: O -bromoaryl ynones and benzaldehyde oxime

An effective transition-metal-free strategy was developed for the preparation of chromones from o-bromoaryl ynones and benzaldehyde oxime through sequential C-O bond formation. This cyclization reaction could well tolerate a wide range of functional groups, and the corresponding chromones were given in moderate to excellent yields. Mechanistically, benzaldehyde oxime as a hydroxide source and 1,3-diketone derivatives as reaction intermediates were involved in this transformation.

Application of α- and β-naphthoflavones as monooxygenase inhibitors of Absidia coerulea KCh 93, Syncephalastrum racemosum KCh 105 and Chaetomium sp. KCh 6651 in transformation of 17α-methyltestosterone

In this work, 17α-methyltestosterone was effectively hydroxylated by Absidia coerulea KCh 93, Syncephalastrum racemosum KCh 105 and Chaetomium sp. KCh 6651. A. coerulea KCh 93 afforded 6β-, 12β-, 7α-, 11α-, 15α-hydroxy derivatives with 44%, 29%, 6%, 5% and 9% yields, respectively. S. racemosum KCh 105 afforded 7α-, 15α- and 11α-hydroxy derivatives with yields of 45%, 19% and 17%, respectively. Chaetomium sp. KCh 6651 afforded 15α-, 11α-, 7α-, 6β-, 9α-, 14α-hydroxy and 6β,14α-dihydroxy derivatives with yields of 31%, 20%, 16%, 7%, 5%, 7% and 4%, respectively. 14α-Hydroxy and 6β,14α-dihydroxy derivatives were determined as new compounds. Effect of various sources of nitrogen and carbon in the media on biotransformations were tested, however did not affect the degree of substrate conversion or the composition of the products formed. The addition of α- or β-naphthoflavones inhibited 17α-methyltestosterone hydroxylation but did not change the percentage composition of the resulting products.

FeCl3 and ether mediated direct intramolecular acylation of esters and their application in efficient preparation of xanthone and chromone derivatives

The direct intramolecular acylation of esters was developed by using the combined system of FeCl3 with Cl2CHOCH3. This unique cooperative system offered a new and efficient approach to biologically important xanthone and chromone derivatives with regioselectivity. Examples were reported, and control experiments were carried out to examine the effect of the benzyl esters and Cl2CHOCH3.