2-(3,4-Dimethoxyphenyl)benzo[h]chromen-4-one

Base Information

• Chemical Name: 2-(3,4-Dimethoxyphenyl)benzo[h]chromen-4-one
• CAS No.: 14756-24-2
• Molecular Formula: C21H16O4
• Molecular Weight: 332.356
• European Community (EC) Number: 694-564-0
• NSC Number: 123391
• DSSTox Substance ID: DTXSID5058690
• Nikkaji Number: J1.221.712I
• Wikidata: Q81976907
• Metabolomics Workbench ID: 74548
• ChEMBL ID: CHEMBL2420083
• Mol file: 14756-24-2.mol

Synonyms:3',4'-dimethoxy-alpha-naphthoflavone

Chemical Property of 2-(3,4-Dimethoxyphenyl)benzo[h]chromen-4-one

Chemical Property:

• Vapor Pressure: 1.15E-10mmHg at 25°C
• Boiling Point: 513.8oC at 760 mmHg
• Flash Point: 227.3oC
• PSA: 48.67000
• Density: 1.271g/cm3
• LogP: 4.63040
• Storage Temp.: 2-8°C
• Solubility.: DMSO: ≥13mg/mL
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 332.10485899
• Heavy Atom Count: 25
• Complexity: 528

Purity/Quality:

98.5% ^*data from raw suppliers

DiMNF ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T
• Statements: 25
• Safety Statements: 45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C(C=C1)C2=CC(=O)C3=C(O2)C4=CC=CC=C4C=C3)OC
• Description: DiMNF (14756-24-2) is a selective aryl hydrocarbon receptor (AHR) modulator (SAhRM). It exhibits antiinflammatory activity including suppression of cytokine-mediated acute phase genes through dissociation of non-dioxin-response element (DRE) AHR activity from DRE-dependent xenobiotic gene expression.1?DiMNF represses the cytokine-mediated induction of CD55 and therefore may have therapeutic potential in regulating the immune response to tumor formation.2?Represses estrogen-inducible transcription.3
• Uses: 3',4'-Dimethoxy-α-naphthoflavone (DiMNF) is a potent and selective aryl hydrocarbon receptor (AHR) modulator (SAhRM). Studies show that DiMNF suppresseses cytokine-mediated complement factor gene expression through selective activation of the Ah receptor. DiMNF has therapeutic potential in regulating the immune response to tumor formation. 3'',4''-Dimethoxy-α-naphthoflavone (DiMNF) is a potent and selective aryl hydrocarbon receptor (AHR) modulator (SAhRM). Studies show that DiMNF suppresseses cytokine-mediated complement factor gene expression through selective activation of the Ah receptor. DiMNF has therapeutic potential in regulating the immune response to tumor formation.

Technology Process of 2-(3,4-Dimethoxyphenyl)benzo[h]chromen-4-one

There total 6 articles about 2-(3,4-Dimethoxyphenyl)benzo[h]chromen-4-one 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: 64.0%

(E)-3-(3,4-dimethoxyphenyl)-1-(1-hydroxynaphthalen-2-yl)prop-2-en-1-one (125574-13-2) → 3',4'-Dimethoxy-alpha-naphathoflavone (14756-24-2)

Guidance literature:

With iodine; In dimethyl sulfoxide; Reflux;

DOI:10.1016/j.ejmech.2013.06.035

Reference yield:

3,4-dimethoxy-benzaldehyde (120-14-9) → 3',4'-Dimethoxy-alpha-naphathoflavone (14756-24-2)

Guidance literature:

Multi-step reaction with 2 steps

1: ethanol / 20 °C / Alkaline conditions

2: iodine / dimethyl sulfoxide / Reflux

With iodine; In ethanol; dimethyl sulfoxide; 1: |Claisen-Schmidt Condensation;

DOI:10.1016/j.ejmech.2013.06.035

Reference yield:

1-hydroxy-2-acetonaphthone (711-79-5) → 3',4'-Dimethoxy-alpha-naphathoflavone (14756-24-2)

Guidance literature:

Multi-step reaction with 2 steps

1: ethanol / 20 °C / Alkaline conditions

2: iodine / dimethyl sulfoxide / Reflux

With iodine; In ethanol; dimethyl sulfoxide; 1: |Claisen-Schmidt Condensation;

DOI:10.1016/j.ejmech.2013.06.035

upstream raw materials:

methyl iodide

(E)-3-(3,4-dimethoxyphenyl)-1-(1-hydroxynaphthalen-2-yl)prop-2-en-1-one

3,4-dimethoxy-benzaldehyde

1-hydroxy-2-acetonaphthone

Refernces