2-hydroxy-3-(hexadecyloxy)-propyl 2-trimethylammonioethyl phosphate

Base Information

• Chemical Name: 2-hydroxy-3-(hexadecyloxy)-propyl 2-trimethylammonioethyl phosphate
• CAS No.: 78119-19-4
• Molecular Formula: C₂₄H₅₂NO₆P
• Molecular Weight: 481.654
• DSSTox Substance ID: DTXSID601297165
• Wikidata: Q27115820
• Mol file: 78119-19-4.mol

Synonyms:2-hydroxy-3-(hexadecyloxy)-propyl 2-trimethylammonioethyl phosphate

Chemical Property of 2-hydroxy-3-(hexadecyloxy)-propyl 2-trimethylammonioethyl phosphate

Chemical Property:

• XLogP3: 5.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 24
• Exact Mass: 481.35322538
• Heavy Atom Count: 32
• Complexity: 450

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

Technology Process of 2-hydroxy-3-(hexadecyloxy)-propyl 2-trimethylammonioethyl phosphate

There total 29 articles about 2-hydroxy-3-(hexadecyloxy)-propyl 2-trimethylammonioethyl phosphate 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%

Rac. 1-O-Hexadecyl-2-O-benzylglycero-3-phosphocholin (18678-98-3) → 2-hydroxy-3-(hexadecyloxy)-propyl 2-trimethylammonioethyl phosphate (78119-19-4,17364-21-5)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; Ambient temperature;

DOI:10.1016/0009-3084(94)02405-T

Reference yield: 100.0%

3-O-hexadecyl-2-O-benzyl-sn-glycero-1-phosphocholine (96998-53-7) → 2-hydroxy-3-(hexadecyloxy)-propyl 2-trimethylammonioethyl phosphate (78119-19-4,17364-21-5)

Guidance literature:

With hydrogen; palladium; In ethanol; at 50 ℃; for 72h; under 760 Torr;

DOI:10.1248/cpb.33.572

Reference yield: 73.4%

choline phosphate (645-84-1) + cetyl glycidyl ether (117606-92-5,121403-67-6,123483-78-3,15965-99-8) → 2-hydroxy-3-(hexadecyloxy)-propyl 2-trimethylammonioethyl phosphate (78119-19-4,17364-21-5)

Guidance literature:

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

DOI:10.1007/BF02333883

upstream raw materials:

Rac_. 1-O-Hexadecyl-2-O-benzylglycero-3-phosphocholin

cetyl glycidyl ether

3-O-hexadecyl-2-O-benzyl-sn-glycero-1-phosphocholine

trimethylamine

Downstream raw materials:

1-O-hexadecyl-2-O-methylglycero-3-phosphocholine

PAF

carbamyl-PAF

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

Refernces

• 1、 Malekin,Khromova,Kisin,Kruglyak,Kurochkin. "Synthesis and chemical transformations of 4-hexadecyloxymethyl-2-oxo-2-chloro-1,3,2-dioxaphospholane". . p. 677 - 682. Retrieved 2007/10/03.
• 2、 Rattay, Bernd,Brezesinski, Gerald,Dobner, Bodo,Foerster, Guenter,Nuhn, Peter. "Influence of α-branched fatty acid chains on the thermotropic behaviour of racemic 1-O-hexadecyl-2-acyl-glycero-3-phosphocholines". . p. 81 - 92. Retrieved 2007/10/02.