Lyso-PAF c-18

Base Information

• Chemical Name: Lyso-PAF c-18
• CAS No.: 72490-82-5
• Deprecated CAS: 34240-68-1
• Molecular Formula: C26H56NO6P
• Molecular Weight: 509.707
• DSSTox Substance ID: DTXSID20955785
• Wikidata: Q27163081
• Metabolomics Workbench ID: 127872
• ChEMBL ID: CHEMBL229361
• Mol file: 72490-82-5.mol

Synonyms:Lyso-PAF c-18;72490-82-5;(2-hydroxy-3-octadecoxypropyl) 2-(trimethylazaniumyl)ethyl phosphate;1-octadecylglycero-3-phosphocholine;Ro 14-0859;LPC O-18:0;2-hydroxy-3-(octadecyloxy)propyl 2-(trimethylazaniumyl)ethyl phosphate;4,7-DihydroXY-N,N,N-trimethyl-2,5,9-trioxa-4-phosphaheptacosan-1-aminium hydroxide, inner salt, 4-oxide, (+-)-;CHEMBL229361;SCHEMBL7592842;CHEBI:91144;DTXSID20955785;lyso-PC (O-18:0/0:0);Choline hydroxide, 2-hydroxy-3-(octadecyloxy)propyl hydrogen phosphate, inner salt;LS-53243;rac-1-Octadecyl-lyso-glycerophosphocholine;FT-0641518;O-0260;O-0262;Q27163081;(2-Hydroxy-3-octadecoxypropyl)2-(trimethylazaniumyl)ethyl phosphate;2,5,9-Trioxa-4-phosphaheptacosan-1-aminium, 4,7-dihydroXY-N,N,N-trimethyl-, hydroxide, inner salt, 4-oxide, (+-)-;3,5,9-Trioxa-4-phosphaheptacosan-1-aminium, 4,7-dihydroxy-N,N,N-trimethyl-, hydroxide, inner salt, 4-oxide, (+-)-;34240-68-1

Chemical Property of Lyso-PAF c-18

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Density: g/cm³
• XLogP3: 7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 26
• Exact Mass: 509.38452550
• Heavy Atom Count: 34
• Complexity: 478

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCCCCCCCCOCC(COP(=O)([O-])OCC[N+](C)(C)C)O

Technology Process of Lyso-PAF c-18

There total 13 articles about Lyso-PAF c-18 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: 71.8%

choline phosphate (645-84-1) + octadecyl glycidyl ether (16245-97-9) → 2-hydroxy-3-(octadecyloxy)propyl 2-(trimethylammonio)ethyl phosphate (72490-82-5,34240-68-1)

Guidance literature:

With phosphocholine sodium salt; In methanol; for 20h; Heating;

DOI:10.1007/BF02333883

Reference yield:

C33H62NO6P (43043-61-4) → 2-hydroxy-3-(octadecyloxy)propyl 2-(trimethylammonio)ethyl phosphate (72490-82-5,34240-68-1)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; at 50 ℃; for 5h; Yield given;

DOI:10.1016/S0040-4039(00)99049-X

Reference yield:

2-(benzyloxy)-3-(octadecyloxy)-1-propanol (86008-21-1,89104-47-2) → 2-hydroxy-3-(octadecyloxy)propyl 2-(trimethylammonio)ethyl phosphate (72490-82-5,34240-68-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) Et₃N, 2.) Et₃N, water / 1.) diethyl ether, RT, 5 h, 2.) diethyl ether, reflux, 2 h

2: CHCl₃; propan-2-ol; dimethylformamide / 12 h / 50 °C

3: H₂ / 10percent Pd/C / ethanol / 12 h / 40 °C / 1034.3 Torr

With water; hydrogen; triethylamine; palladium on activated charcoal; In ethanol; chloroform; N,N-dimethyl-formamide; isopropyl alcohol;

DOI:10.1021/jm00388a008

upstream raw materials:

C₃₃H₆₂NO₆P

choline phosphate

octadecyl glycidyl ether

batyl alcohol

Downstream raw materials:

1-O-octadecyl-2-acetyl-sn-glycero-3-phosphocholine

Refernces

• 1、 Noskov,Shishkov,Kruglyak,Kiselevskii,Dobryanskii,Maksimtseva,Sokal'skii. "Synthesis and antihypertensive activity of some 1-O-alkylglycero-3-phosphocholine derivatives". . p. 607 - 610. Retrieved 2007/10/03.
• 2、 Marx,Wiley. "Synthesis of platelet activating factor (PAF) via a cyclic tin intermediate". . p. 1379 - 1380. Retrieved 2007/10/02.