Visnagin

Base Information

• Chemical Name: Visnagin
• CAS No.: 82-57-5
• Molecular Formula: C13H10O4
• Molecular Weight: 230.22
• Hs Code.: 29162000
• European Community (EC) Number: 201-430-3
• NSC Number: 100593
• UNII: P64438MLBW
• DSSTox Substance ID: DTXSID50231509
• Nikkaji Number: J4.613B
• Wikipedia: Visnagin
• Wikidata: Q7936365
• Pharos Ligand ID: 2GT5V397ZWUD
• Metabolomics Workbench ID: 27988
• ChEMBL ID: CHEMBL45176
• Mol file: 82-57-5.mol

Synonyms:visnagin

Chemical Property of Visnagin

Chemical Property:

• Appearance/Colour: beige fine crystalline powder
• Vapor Pressure: 6.4E-06mmHg at 25°C
• Melting Point: 139-142 °C
• Refractive Index: 1.613
• Boiling Point: 378.2 °C at 760 mmHg
• Flash Point: 182.5 °C
• PSA: 52.58000
• Density: 1.308 g/cm³
• LogP: 2.85620
• Storage Temp.: 2-8°C
• Solubility.: Soluble in DMSO (up to 25 mg/ml) or in Ethanol (up to 25 mg/ml).
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 230.05790880
• Heavy Atom Count: 17
• Complexity: 362

Purity/Quality:

98%, ^*data from raw suppliers

Visnagin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=O)C2=C(O1)C=C3C(=C2OC)C=CO3
• Description: Visnagin (82-57-5) is a natural product isolated from the plant Ammi visnaga.? It displays protective effects against doxorubicin-induced cardiomyopathy via inhibition of mitochondrial malate dehydrogenase resulting in a decrease in cardiomyocyte apoptosis.1
• Uses: antiinflammatory, neuroprotective

Technology Process of Visnagin

There total 22 articles about Visnagin 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: 60.0%

4-Methoxy-7-methyl-9-methylsulfanyl-furo[3,2-g]chromen-5-one (122822-92-8) → visnagin (82-57-5)

Guidance literature:

With nickel; In ethanol;

DOI:10.1021/jo00280a002

Reference yield:

6-Ethoxy-4-methoxy-7-methylsulfanyl-5-vinyl-benzofuran (122822-89-3) → visnagin (82-57-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 75 percent / O₂ gas / PdCl₂, CuCl₂ / dimethylformamide; H₂O / 25 °C

2: 70 percent / BF₃*Et₂O / CH₂Cl₂ / 0 - 25 °C

3: 1.) NaH, 2.) 1N HCl / 1.) THF, reflux, 5 h, 2.) MeOH, 25 deg C

4: 60 percent / Raney Ni / ethanol

With hydrogenchloride; boron trifluoride diethyl etherate; oxygen; nickel; sodium hydride; copper dichloride; palladium dichloride; In ethanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jo00280a002

Reference yield:

Acetic acid 6-ethoxy-7-methylsulfanyl-5-vinyl-benzofuran-4-yl ester (122822-88-2) → visnagin (82-57-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 86 percent / NaH / tetrahydrofuran / 0 - 25 °C

2: 75 percent / O₂ gas / PdCl₂, CuCl₂ / dimethylformamide; H₂O / 25 °C

3: 70 percent / BF₃*Et₂O / CH₂Cl₂ / 0 - 25 °C

4: 1.) NaH, 2.) 1N HCl / 1.) THF, reflux, 5 h, 2.) MeOH, 25 deg C

5: 60 percent / Raney Ni / ethanol

With hydrogenchloride; boron trifluoride diethyl etherate; oxygen; nickel; sodium hydride; copper dichloride; palladium dichloride; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jo00280a002

upstream raw materials:

tetrahydrovisnagin

6-hydroxy-4-methoxy-5-acetoacetylbenzofuran

(7-hydroxy-5-methoxy-2-methyl-4-oxo-4H-chromen-6-yl)-acetaldehyde

7-chloromethyl-4-methoxy-furo[3,2-g]chromen-5-one

Downstream raw materials:

MRS 1065

Norisovisnagin

5-acetyl-4-methoxybenzofuran-6-ol

6-hydroxy-4-methoxybenzofuran-5-carboxylic acid

Refernces

Concise synthesis of 5-methoxy-6-hydroxy-2-methylchromone-7-O- and 5-hydroxy-2-methylchromone-7-O-rutinosides. Investigation of their cytotoxic activities against several human tumor cell lines

10.1021/jo102325s

The research aimed to develop a concise synthetic strategy for the production of two novel 2-methylchromone-7-O-rutinosides, which are flavonoid glycosides with potential cytotoxic activities against human tumor cell lines. The study was driven by the bioactivities of these compounds, particularly their potential as antitumor agents with low side effects on normal cells. The synthesis process involved the use of various chemicals, including Visnagin, chromic acid, hydrogen peroxide, 2,3,4,6-tetra-O-acetyl-R-D-glucosyl bromide, Bu4NBr, K2CO3, 1,4-diazabicyclo[2.2.2]octane (DABCO), trityl chloride, bismuth trichloride, and trichloroacetimidate derivatives. The researchers successfully synthesized the target compounds and evaluated their in vitro cytotoxicity against several human cancer cell lines.

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