alpha-Naphthoflavone

Base Information

• Chemical Name: alpha-Naphthoflavone
• CAS No.: 604-59-1
• Molecular Formula: C19H12O2
• Molecular Weight: 272.303
• Hs Code.: 29143990
• European Community (EC) Number: 210-071-1
• NSC Number: 407011
• UNII: FML65D8PY5
• DSSTox Substance ID: DTXSID2040650
• Nikkaji Number: J46.330B
• Wikipedia: Alpha-Naphthoflavone
• Wikidata: Q4734915
• Pharos Ligand ID: CL4Q45WU3SB6
• Metabolomics Workbench ID: 74448
• ChEMBL ID: CHEMBL283196
• Mol file: 604-59-1.mol

Synonyms:7,8-benzoflavone;alpha-naphthoflavone

Chemical Property of alpha-Naphthoflavone

Chemical Property:

• Appearance/Colour: yellow powder
• Vapor Pressure: 1.12E-08mmHg at 25°C
• Melting Point: 153-157 °C(lit.)
• Refractive Index: 1.695
• Boiling Point: 460.9 °C at 760 mmHg
• Flash Point: 215.8 °C
• PSA: 30.21000
• Density: 1.276 g/cm³
• LogP: 4.61320
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)
• XLogP3: 4.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 272.083729621
• Heavy Atom Count: 21
• Complexity: 433

Purity/Quality:

99% ^*data from raw suppliers

α-Naphthylflavone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn,C,F
• Hazard Codes: Xi,Xn,C,F
• Statements: 68-34-11
• Safety Statements: 24/25-36/37-45-36/37/39-26-16

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Uses -> Biochemical Research
• Canonical SMILES: C1=CC=C(C=C1)C2=CC(=O)C3=C(O2)C4=CC=CC=C4C=C3
• 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] 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.

Technology Process of alpha-Naphthoflavone

There total 31 articles about alpha-Naphthoflavone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

2-phenyl-2H-benzo[h]chromen-4(3H)-one (6051-86-1) → α-naphtoflavone (604-59-1)

Guidance literature:

With thallium(III) acetate; In acetic acid; for 3h; Heating;

Reference yield: 93.0%

1-(1-hydroxy-2-naphthalenyl)-3-phenyl-2-propyn-1-one → α-naphtoflavone (604-59-1)

Guidance literature:

With dmap; In N,N-dimethyl-formamide; at 0 - 30 ℃; for 2h; regioselective reaction; Inert atmosphere;

DOI:10.1016/j.tet.2011.09.063

Reference yield: 89.0%

1-(1-hydroxynaphthalen-2-yl)-3-phenylpropane-1,3-dione (63450-45-3) → α-naphtoflavone (604-59-1)

Guidance literature:

With sulfuric acid; In acetic acid; for 1h; Reflux;

DOI:10.1016/j.bmcl.2017.01.020

upstream raw materials:

1-hydroxy-2-naphthyl styryl ketone

2-acetyl-1-benzoyloxynaphthalene

1-(1-hydroxynaphthalen-2-yl)-3-phenylpropane-1,3-dione

α-naphthol

Downstream raw materials:

2-phenyl-4H-benzo[h]chromene-4-thione

1-Phenyl-1-(phenylthio)-3-(2-naphthyl)-prop-1-ene-3-thione

benzoic acid

2-phenyl-4H-benzo[h]chromene

Refernces

• 1、 Zhang, Jing-Wen,Yang, Wan-Wan,Chen, Lu-Lu,Chen, Pei,Wang, Yan-Bo,Chen, Dan-Yun. "An efficient tandem synthesis of chromones from: O -bromoaryl ynones and benzaldehyde oxime". . p. 7461 - 7467. Retrieved 2019/08/20.
• 2、 Singh, Harbinder,Singh, Jatinder Vir,Gupta, Manish K.,Singh, Palwinder,Sharma, Sahil,Nepali, Kunal,Bedi, Preet Mohinder S.. "Benzoflavones as cholesterol esterase inhibitors: Synthesis, biological evaluation and docking studies". . p. 850 - 854. Retrieved 2017/02/12.