82855-09-2

Basic information

• Product Name: COMBRETASTATIN
• Synonyms: COMBRETASTATIN;(R)-(-)-Combretastatin;(R)-3-Hydroxy-4-methoxy-α-(3,4,5-trimethoxyphenyl)benzeneethanol;2-Methoxy-5-[(βR)-β-hydroxy-3,4,5-trimethoxyphenethyl]phenol;5-[(R)-2-Hydroxy-2-(3,4,5-trimethoxyphenyl)ethyl]-2-methoxyphenol
• CAS NO: 82855-09-2
• Molecular Formula: C₁₈H₂₂O₆
• Molecular Weight: 334.36
• Mol File: 82855-09-2.mol
• Article Data: 9

Chemical Properties

• Melting Point: 130-131°
• Boiling Point: 485.3°C at 760 mmHg
• Flash Point: 247.3°C
• Appearance: /
• Density: 1.33
• Vapor Pressure: 3.14E-10mmHg at 25°C
• Refractive Index: 1.569
• CAS DataBase Reference: COMBRETASTATIN(CAS DataBase Reference)
• NIST Chemistry Reference: COMBRETASTATIN(82855-09-2)
• EPA Substance Registry System: COMBRETASTATIN(82855-09-2)

Safety Data

• Hazardous Substances Data: 82855-09-2(Hazardous Substances Data)

Usage

General Description

Combretastatin is a family of natural organic compounds that have demonstrated potent anti-cancer and anti-angiogenic properties. Derived from Combretum caffrum, also known as the bushwillow, combretastatins have been found to disrupt the formation of new blood vessels in tumors, thereby inhibiting their growth and spread. They function by binding to and destabilizing the cytoskeleton of endothelial cells, leading to their death and preventing the formation of new blood vessels. Combretastatins have shown promise in clinical trials for the treatment of various types of cancer, and are being developed as potential therapeutic agents for fighting the disease.

InChI:InChI=1/C18H22O6/c1-21-15-6-5-11(8-14(15)20)7-13(19)12-9-16(22-2)18(24-4)17(10-12)23-3/h5-6,8-10,13,19-20H,7H2,1-4H3/t13-/m0/s1

Upstream product

• 388566-85-6 (E)-5-(2-bromoethenyl)-2-methoxyphenol 
• 388566-84-5 (Z)-5-(2'-bromoethenyl)-2-methoxyphenol 
• 108-95-2 phenol 
• 177329-70-3 (S)-1-(3,4,5-trimethoxyphenyl)-2-(p-toluenesulfonyloxy)ethanol 
• 177329-69-0 (S)-1-(3,4,5-trimethoxyphenyl)-1,2-ethanediol 
• 177472-80-9 (2S)-2-(3,4,5-trimethoxyphenyl)oxirane 
• 177329-71-4 5-Bromo-1-(tert-butyldimethylsilyloxy)-2-methoxybenzene 
• 86-81-7 3,4,5-trimethoxy-benzaldehyde 
• 37942-01-1 5-bromo-2-methoxyphenol 
• 13400-02-7 3,4,5-trimethoxy styrene 
• 97315-21-4 (R)-2-(3-tert-butyldimethylsilyloxy-4-methoxy)phenyl-1-(3,4,5-trimethoxyphenyl)ethanol 
• 97315-17-8 5-<(tert-butyldimethylsilyl)oxy>-(+/-)-combretastatin 
• 97315-18-9 p-methoxy-m-(tert-butyldimethylsilyloxy)-benzaldehyde 
• 97315-20-3 3-<(tert-butyldimethylsilyl)oxy>-4-methoxybenzyl bromide 

Relevant articles and documents

Catalytic conjunctive cross-coupling enabled by metal-induced metallate rearrangement

Transition metal catalysis plays a central role in contemporary organic synthesis. Considering the tremendously broad array of transition metal-catalyzed transformations, it is remarkable that the underlying elementary reaction steps are relatively few in

Combrestatin a-1 phosphate and combrestatin b-1 phosphate prodrugs

The present invention relates to the syntheses and structural elucidation of Combretastatin A1-Phosphate Prodrugs and Combretastatin B1-Phosphate Prodrugs and the utilization of those prodrugs in the treatment of neoplastic diseases. The prodrugs described herein have the structure: Combretastin A-1 Phosphate Prodrug (I) and Combretastin B-1 Phosphate Prodrug (II).

Enantioselective synthesis of natural combretastatin

In a process which appears to be general for the enantioselective synthesis of oxysubstituted 1,2-diarylethanols, a 4-methoxy-3-silyloxyphenyllithium, obtained by bromine-lithium exchange from the corresponding aryl bromide and t-butyllithium, added selectively at the b-carbon of (S)-2,3,4-trimethoxyphenyloxirane, elaborated from the corresponding styrene via Sharpless asymmetric dihydroxylation, to afford an adduct from which natural (-)-combretastatin was obtained by desilylation.