Ampelopsin F

Base Information

• Chemical Name: Ampelopsin F
• CAS No.: 151487-08-0
• Molecular Formula: C₂₈H₂₂O₆
• Molecular Weight: 454.479

Synonyms:(+)-AmpelopsinF; Ampelopsin F

Chemical Property of Ampelopsin F

Chemical Property:

• PSA: 121.38000
• LogP: 5.07860

Purity/Quality:

≥98% ^*data from raw suppliers

AmpelopsinF ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• General Description: Ampelopsin F is a stilbene dimer with notable antioxidant and anti-inflammatory properties, synthesized through a practical route involving triethylsilane-mediated reduction and BBr3-mediated demethylation and cyclization, achieving a 10% yield, which facilitates further study and application of this bioactive compound and its analogues.

Technology Process of Ampelopsin F

There total 13 articles about Ampelopsin F 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: 90.0%

permethyl ampelopsin F → (+)-ampelopsin F (151487-08-0)

Guidance literature:

permethyl ampelopsin F; With boron tribromide; In dichloromethane; at 0 - 25 ℃; for 19h;

With water; In dichloromethane;

Reference yield: 90.0%

C34H34O6 → (+)-isoampelopsin F (354528-90-8,151487-08-0)

Guidance literature:

With boron tribromide; In dichloromethane; at 0 - 25 ℃; for 19h; Inert atmosphere;

Reference yield: 83.0%

C34H34O6 → (+/-)-ampelopsin F (151487-08-0)

Guidance literature:

With boron tribromide; In dichloromethane; at 0 - 25 ℃; for 19h;

DOI:10.1002/anie.200703333

upstream raw materials:

5-{6-hydroxy-2-(4-hydroxyphenyl)-4-[2-(4-hydroxyphenyl)vinyl]-2,3-dihydrobenzofuran-3-yl}benzene-1,3-diol

C₃₂H₃₀O₆

Refernces

A facile and practical total synthetic route for ampelopsin F and permethylated ?-viniferin

10.1055/s-0035-1561419

The research aims to develop a practical and efficient synthetic route for the production of stilbene dimers, specifically (±)-ampelopsin F and permethylated (±)-εviniferin, which are known for their antioxidant, anti-inflammatory, and other biological activities. The study addresses the scarcity of these compounds, which are typically obtained through extraction from natural sources, by offering a synthetic approach that involves triethylsilane-mediated reduction of the 2,3-diarylbenzofuran and BBr3-mediated one-pot demethylation and cascade intramolecular cyclization reaction. The conclusions of the research highlight the successful synthesis of the target compounds with overall yields of 10% and 27%, respectively, through a concise and practical route that could be useful for the synthesis of these compounds and their analogues, although the synthesis of (±)-ε-viniferin (2) is still in progress.

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