Edelfosine

Base Information

• Chemical Name: Edelfosine
• CAS No.: 70641-51-9
• Deprecated CAS: 122130-64-7,119225-10-4,65492-82-2,195154-26-8
• Molecular Formula: C₂₇H₅₈NO₆P
• Molecular Weight: 523.734
• NSC Number: 343649,324368
• UNII: 1Y6SNA8L5S
• DSSTox Substance ID: DTXSID9045766
• Wikipedia: Edelfosine
• Wikidata: Q3579094
• NCI Thesaurus Code: C956
• ChEMBL ID: CHEMBL28509
• Mol file: 70641-51-9.mol

Synonyms:1-O-octadecyl-2-methyl-3-phosphatidylcholine;1-O-octadecyl-2-O-methyl-glycero-phosphocholine;1-O-octadecyl-2-O-methyl-rac-glycero-3-phosphocholine;1-O-octadecyl-2-O-methylglycerophosphocholine;1-octadecyl-2-methoxy-sn-glycero-3-phosphorylcholine;1-octadecyl-2-methoxyglycero-3-phosphorylcholine;1-octadecyl-2-methyl-sn-glycero-3-phosphocholine;1-octadecyl-2-methylglycero-3-phosphocholine;2-methoxy-PAF;edelfosine;edelfosine, (+-)-isomer;edelfosine, (R)-isomer;edelfosine, (S)-isomer;ET-18-O-methyl;ET-18-OCH(3);ET-18-OCH3;ET18-OCH3;ET18-OMe;L-ET-18-OCH3;TLC ELL-12

Chemical Property of Edelfosine

Chemical Property:

• Appearance/Colour: waxy solid
• PSA: 86.86000
• LogP: 7.55750
• Storage Temp.: −20°C
• Solubility.: ethanol: 15 mg/mL at 45 °C, soluble
• XLogP3: 7.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 27
• Exact Mass: 523.40017557
• Heavy Atom Count: 35
• Complexity: 492

Purity/Quality:

98%,99%, ^*data from raw suppliers

ET-18-OCH3 ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCCCCCCCCOCC(COP(=O)([O-])OCC[N+](C)(C)C)OC
• Uses: Edelfosine has been used to treat human lung carcinoma A549 cells and study its effects on tuftelin 1 (TUFT1) expression. It is also used to evaluate the cell growth of MCF-7/M cells.

Technology Process of Edelfosine

There total 6 articles about Edelfosine 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:

2-methoxy-3-octadecyloxy-1-propanol (84337-43-9) → Edelfosine (70641-51-9,65492-82-2,77286-66-9)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine / benzene / 2 h / O deg C to room temp.

2: H₂O / 1.5 h / Heating

3: 2.) Ag₂CO₃ / 1.) toluene, 3 d, room temp., 2.) methanol, 1.5 h reflux

With pyridine; silver carbonate; In water; benzene;

DOI:10.1248/cpb.30.3260

Reference yield:

Phosphorochloridic acid 2-bromo-ethyl ester 2-methoxy-3-octadecyloxy-propyl ester → Edelfosine (70641-51-9,65492-82-2,77286-66-9)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂O / 1.5 h / Heating

2: 2.) Ag₂CO₃ / 1.) toluene, 3 d, room temp., 2.) methanol, 1.5 h reflux

With silver carbonate; In water;

DOI:10.1248/cpb.30.3260

Reference yield:

1-Bromooctadecane (112-89-0) → Edelfosine (70641-51-9,65492-82-2,77286-66-9)

Guidance literature:

Multi-step reaction with 4 steps

1: KOH / tetrahydrofuran; dimethylsulfoxide / 2 h / Ambient temperature

2: pyridine / benzene / 2 h / O deg C to room temp.

3: H₂O / 1.5 h / Heating

4: 2.) Ag₂CO₃ / 1.) toluene, 3 d, room temp., 2.) methanol, 1.5 h reflux

With pyridine; potassium hydroxide; silver carbonate; In tetrahydrofuran; water; dimethyl sulfoxide; benzene;

DOI:10.1248/cpb.30.3260

upstream raw materials:

2-(2-Methoxy-3-octadecyloxy-propoxy)-[1,3,2]dioxaphospholane 2-oxide

trimethylamine

Phosphoric acid 2-bromo-ethyl ester 2-methoxy-3-octadecyloxy-propyl ester

2-methoxy-3-octadecyloxy-1-propanol

Refernces

In Vitro Evaluation of Phosphocholine and Quaternary Ammonium Containing Lipids as Novel Anti-HIV Agents

10.1021/jm00108a021

The research evaluates a series of synthetic lipids containing a two- or three-carbon backbone substituted with a thio, oxy, or amidoalkyl functionality and either a phosphocholine or quaternary ammonium moiety as potential anti-HIV-1 agents. The most promising compound identified is rac-3-octadecanamido-2-etholrypropylphosphocholine (8), which exhibited an ICso for the inhibition of plaque formation of 0.16 pM, significantly lower than the ICw value determined for CEM-SS cell growth inhibition. Unlike AZT, these compounds appear to inhibit a late step in HIV replication involving virus assembly and infectious virus production. Key chemicals involved in the research include AZT as a reference compound, various phospholipid analogues such as ET-18-OMe, ET-18-OEt, and compound 8, as well as nonphosphorus-containing analogues like compounds 20, 22, and 27. The study also involved the synthesis of several compounds, including 2, 3, 17, 24, 26, and 37, using starting materials like 1,2-dimethylethylene phosphorochloridate (CEP-Cl), 2-(isopropylamino)ethanol, 2-(tert-butylamino)ethanol, and other reagents such as p-toluenesulfonyl chloride and dicyclohexylcarbodiimide (DCC).

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