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:

97% ^*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
• General Description: Combretastatin A1 (CA1) is a naturally derived compound from the African bush willow tree, known for its potent antitubulin and vascular-disrupting properties, making it valuable in cancer therapy. It functions by inhibiting tubulin polymerization, thereby disrupting tumor vasculature. COMBRETASTATIN A1 can be synthesized with carbon-14 labeling for research purposes, and its phosphate prodrug (CA1P) enhances bioavailability. The synthesis involves methylation, deprotection, and phosphorylation steps, yielding a product with high radiochemical purity and specific activity.

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)-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

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

Refernces

Carbon-14 radiosynthesis of combretastatin A-1 (CA1) and its corresponding phosphate prodrug (CA1P)

10.1002/JLCR.1676

The research focuses on the carbon-14 radiosynthesis of combretastatin A-1 (CA1) and its phosphate prodrug CA1P, which are derived from the African bush willow tree and have significant medicinal value due to their ability to inhibit tubulin assembly and act as vascular disrupting agents in cancer treatment. The study details a four-step synthesis process to incorporate carbon-14 into CA1 and CA1P with high specific activity. Key reactants include the CA1 precursor, [14C]methyl iodide for radiolabeling, TiCl4 for deprotection, and dibenzyl phosphite for phosphorylation. The methodology involves methylation of the C-4 protected phenolic moiety, de-isopropylation with TiCl4, and conversion to the phosphate prodrug. Analyses were performed using 1H NMR, analytical HPLC, and radio-TLC to ensure chemical and radiochemical purities, with the final product achieving a specific activity of 55 mCi/mmol.

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