Combretastatin A-1

Base Information

• Chemical Name: Combretastatin A-1
• CAS No.: 109971-63-3
• Molecular Formula: C18H20O6
• Molecular Weight: 332.353
• Hs Code.: 2909499000
• NSC Number: 600032
• UNII: 2222ATS339
• DSSTox Substance ID: DTXSID701028842
• Nikkaji Number: J435.579B
• Wikipedia: Combretastatin_A-1
• NCI Thesaurus Code: C162344
• Metabolomics Workbench ID: 132875
• ChEMBL ID: CHEMBL36255
• Mol file: 109971-63-3.mol

Synonyms:combretastatin A-1;Combretastatin A1;NSC 600032;NSC-600032

Chemical Property of Combretastatin A-1

Chemical Property:

• Vapor Pressure: 8.82E-12mmHg at 25°C
• Melting Point: 113-115 °C(Solv: chloroform (67-66-3); hexane (110-54-3))
• Refractive Index: 1.627
• Boiling Point: 528.4 °C at 760 mmHg
• PKA: 8.89±0.45(Predicted)
• Flash Point: 273.3 °C
• PSA: 77.38000
• Density: 1.251 g/cm³
• LogP: 3.30260
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 332.12598835
• Heavy Atom Count: 24
• Complexity: 387

Purity/Quality:

99% ^*data from raw suppliers

(Z)-3-Methoxy-6-(3,4,5-trimethoxystyryl)benzene-1,2-diol 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C(=C(C=C1)C=CC2=CC(=C(C(=C2)OC)OC)OC)O)O
• Isomeric SMILES: COC1=C(C(=C(C=C1)/C=C\C2=CC(=C(C(=C2)OC)OC)OC)O)O

Technology Process of Combretastatin A-1

There total 20 articles about Combretastatin A-1 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: 100.0%

(Z)-1-[3',4',5'-trimethoxyphenyl]-2-[(2'',3''-di[(tert-butyldimethylsilyl)oxy]-4''-methoxy)phenyl]ethene (109971-68-8) → (Z)-3-methoxy-6-(3,4,5-trimethoxystyryl)benzene-1,2-diol (109971-63-3)

Guidance literature:

With potassium fluoride; hydrogen bromide; In N,N-dimethyl-formamide; for 2h; Sonication;

DOI:10.1021/np800661r

Reference yield: 77.0%

C22H28O8 (444992-85-2) → (Z)-3-methoxy-6-(3,4,5-trimethoxystyryl)benzene-1,2-diol (109971-63-3)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran;

DOI:10.1016/S0040-4039(02)00389-1

Reference yield: 74.0%

1-methoxy-2,3-bis(methoxymethoxy)-4-((3,4,5-trimethoxyphenyl)-ethynyl)benzene (444992-83-0) → (Z)-3-methoxy-6-(3,4,5-trimethoxystyryl)benzene-1,2-diol (109971-63-3)

Guidance literature:

1-methoxy-2,3-bis(methoxymethoxy)-4-((3,4,5-trimethoxyphenyl)-ethynyl)benzene; With bis(cyclohexanyl)borane; In tetrahydrofuran; at 0 ℃;

With hydrogenchloride; In tetrahydrofuran; water;

DOI:10.1016/j.tetlet.2005.12.037

upstream raw materials:

(Z)-1-[3',4',5'-trimethoxyphenyl]-2-[(2'',3''-di[(tert-butyldimethylsilyl)oxy]-4''-methoxy)phenyl]ethene

C₂₂H₂₈O₈

1-methoxy-2,3-bis(methoxymethoxy)-4-((3,4,5-trimethoxyphenyl)-ethynyl)benzene

1-iodo-4-methoxy-2,3-bis(methoxymethoxy)benzene

Downstream raw materials:

(Z)-1-[3',4',5'-trimethoxyphenyl]-2-[2'',3''-di[([bis[(benzyl)oxy]]phosphoryl)oxy]-4''-methoxyphenyl]ethene

(Z)-3'-hydroxy-3,4,4',5-tetramethoxy-2'-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)stilbene

(Z)-2'-hydroxy-3,4,4',5-tetramethoxy-3'-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)stilbene

3-methoxy-6-[2-(3,4,5-trimethoxyphenyl)-Z-ethylene]-[1,2]benzoquinone

Refernces

• 1、 Coccetti, Paola,Montano, Giuseppe,Lombardo, Alessandro,Tripodi, Farida,Orsini, Fulvia,Pagliarin, Roberto. "Synthesis and biological evaluation of combretastatin analogs as cell cycle inhibitors of the G1 to S transition in Saccharomyces cerevisiae". scheme or table. p. 2780 - 2784. Retrieved 2010/08/19.
• 2、 Odlo, Kristin,Klaveness, Jo,Rongved, P?l,Hansen, Trond Vidar. "Synthesis of combretastatins A-1 and B-1". . p. 1101 - 1103. Retrieved 2007/10/03.