111394-45-7

Basic information

• Product Name: Combretastatin A-3
• Synonyms: Combretastatin A-3
• CAS NO: 111394-45-7
• Molecular Formula: C₁₇H₁₈O₅
• Molecular Weight: 302.324
• Product Categories: Combretastatin
• Mol File: 111394-45-7.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 524.2°Cat760mmHg
• Flash Point: 270.8°C
• Appearance: /
• Density: 1.251g/cm³
• Vapor Pressure: 1.32E-11mmHg at 25°C
• Refractive Index: 1.644
• CAS DataBase Reference: Combretastatin A-3(CAS DataBase Reference)
• NIST Chemistry Reference: Combretastatin A-3(111394-45-7)
• EPA Substance Registry System: Combretastatin A-3(111394-45-7)

Safety Data

• Hazardous Substances Data: 111394-45-7(Hazardous Substances Data)

Usage

General Description

Combretastatin A-3 is a naturally occurring stilbenoid derived from the African tree Combretum caffrum. It is known for its antineoplastic activity and has been widely studied for its potential applications in cancer treatment. Combretastatin A-3 primarily acts by disrupting angiogenesis, that is the formation of new blood vessels, therefore inhibiting the growth and spread of tumor. The molecule exhibits high cytotoxicity towards vascular endothelial cells. It's also been investigated as a possible treatment for age-related macular degeneration. In the medical industry, Combretastatin A-3 has been used as a lead compound for the development of several drugs, including combretastatin A-4 phosphate which has entered clinical trials for various cancers.

InChI:InChI=1/C17H18O5/c1-20-15-7-6-11(8-13(15)18)4-5-12-9-14(19)17(22-3)16(10-12)21-2/h4-10,18-19H,1-3H3/b5-4-

Synthetic route

3,3'-bis-(tert-butyldimethylsilyloxy)-4',4,5-trimethoxy-(Z)-stilbene (111394-58-2) → combretastatin A-3 (111394-45-7)

Conditions	Yield
With tetrabutyl ammonium fluoride In tetrahydrofuran	91%

acetic anhydride (108-24-7) + combretastatin A-3 (111394-45-7) → combretastatin A-3 diacetate (111394-48-0)

Conditions	Yield
With pyridine for 72h; Ambient temperature;

combretastatin A-3 (111394-45-7) → combretastatin B2 (111394-46-8)

Conditions	Yield
With hydrogen; palladium on activated charcoal In methanol Ambient temperature;

Upstream product

• 111394-58-2 3,3'-bis-(tert-butyldimethylsilyloxy)-4',4,5-trimethoxy-(Z)-stilbene 

Downstream Products

• 111394-46-8 combretastatin B₂ 
• 111394-48-0 combretastatin A-3 diacetate 

Relevant articles and documents

Isolation, structure, and synthesis of combretastatin A-2, A-3, and B-2

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