beta-Naphthoflavone

Base Information

• Chemical Name: beta-Naphthoflavone
• CAS No.: 6051-87-2
• Molecular Formula: C19H12 O2
• Molecular Weight: 272.303
• Hs Code.: 2914399090
• European Community (EC) Number: 227-958-4
• NSC Number: 136015
• UNII: 1BT0256Y8O
• DSSTox Substance ID: DTXSID8030423
• Nikkaji Number: J1.840F
• Wikipedia: Beta-Naphthoflavone
• Wikidata: Q4897188
• NCI Thesaurus Code: C29812
• Pharos Ligand ID: J2TVLBPD9DJ4
• Metabolomics Workbench ID: 74447
• ChEMBL ID: CHEMBL26260
• Mol file: 6051-87-2.mol

Synonyms:5,6 Benzoflavone;5,6-Benzoflavone;beta Naphthoflavone;beta-Naphthoflavone

Chemical Property of beta-Naphthoflavone

Chemical Property:

• Appearance/Colour: SLIGHTLY BEIGE CRYSTALLINE POWDER
• Vapor Pressure: 1.12E-08mmHg at 25°C
• Melting Point: 185-189 °C
• Refractive Index: 1.5510 (estimate)
• Boiling Point: 275-280 °C (1 mmHg)
• Flash Point: 215.8°C
• PSA: 30.21000
• Density: 1.276g/cm³
• LogP: 4.61320
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly, Heated)
• XLogP3: 4.4
• 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:

≥98% ^*data from raw suppliers

β-Naphthoflavone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi,C,F
• Hazard Codes: Xn,Xi,C,F
• Statements: 22-34-11
• Safety Statements: 24/25-45-36/37/39-26-16

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C2=CC(=O)C3=C(O2)C=CC4=CC=CC=C43
• General Description: Dulcitol (also known as β-naphthoflavone or BNF) is an aryl hydrocarbon receptor (AhR) agonist whose molecular planarity contributes to its limited solubility. Structural modifications, such as introducing ortho-substituents to disrupt planarity, have been shown to enhance both solubility and AhR-agonistic activity, as demonstrated by analogs like the difluoro derivative (1e), which significantly outperforms the parent compound in potency and solubility. This approach highlights the potential for optimizing AhR ligands through strategic molecular design.

Technology Process of beta-Naphthoflavone

There total 24 articles about beta-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: 100.0%

1-(2-hydroxynaphthalen-1-yl)-3-phenylpropane-1,3-dione (58483-57-1) → 3-phenyl-1H-naphtho[2,1-b]pyran-1-one (6051-87-2)

Guidance literature:

With iodine; In methanol; for 2.5h; Irradiation;

Reference yield: 78.0%

1-(2-tert-butyldimethylsilyloxynaphthalen-1-yl)-3-(4-methylpiperazin-1-yl)-3-phenyl-2-propen-1-one (1219684-05-5) → 3-phenyl-1H-naphtho[2,1-b]pyran-1-one (6051-87-2)

Guidance literature:

With water; In dimethyl sulfoxide; at 90 ℃; for 9.5h; Inert atmosphere;

DOI:10.1016/j.bmc.2009.12.036

Reference yield: 75.0%

(2-hydroxy-[1]naphthyl)-glyoxylic acid + phenylpropyolic acid (637-44-5) → 3-phenyl-1H-naphtho[2,1-b]pyran-1-one (6051-87-2)

Guidance literature:

With dipotassium peroxodisulfate; silver nitrate; In water; acetonitrile; at 80 ℃; for 3h;

DOI:10.1002/adsc.201701469

upstream raw materials:

3-phenyl-2,3-dihydro-1H-benzo[f]chromen-1-one

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

ethyl 3-oxo-3-phenylpropionate

β-naphthol

Downstream raw materials:

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

3-phenyl-1H-naphtho<2,1-b>pyran-1-thione

3-(2-hydroxy-1-naphthyl)-5-(phenyl)-2-isoxazoline

4'-Hydroxy-beta-naphthoflavone

Refernces

β-Naphthoflavone analogs as potent and soluble aryl hydrocarbon receptor agonists: Improvement of solubility by disruption of molecular planarity

10.1016/j.bmc.2009.12.036

The research aimed to develop more potent and soluble aryl hydrocarbon receptor (AhR) agonists by modifying the molecular structure of b-naphthoflavone to disrupt its planarity. The study focused on introducing various substituents at the ortho-positions of the phenyl group to increase the dihedral angle, thereby reducing crystal packing energy and improving aqueous solubility. The most successful analog was the difluoro analog (1e), which exhibited seven times greater AhR-agonistic activity and three times greater solubility compared to b-naphthoflavone. The study concluded that disrupting molecular planarity is an effective strategy for improving the solubility of AhR agonists, offering a novel approach to developing more potent and soluble ligands for AhR research.

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