2,3-Bis(hexadecyloxy)propyl 2-(trimethylammonio)ethyl phosphate

Base Information

• Chemical Name: 2,3-Bis(hexadecyloxy)propyl 2-(trimethylammonio)ethyl phosphate
• CAS No.: 69483-37-0
• Molecular Formula: C40H84 N O6 P
• Molecular Weight: 706.084
• European Community (EC) Number: 274-018-4
• NSC Number: 606171
• DSSTox Substance ID: DTXSID10957677
• ChEMBL ID: CHEMBL1973829
• Mol file: 69483-37-0.mol

Synonyms:1,2-di-O-hexadecyl-rac-glycero-3-phosphocholine;1,2-dihexadecyl-sn-glycero-3-phosphocholine;1,2-dihexadecylphosphatidylcholine;DHPC;dihexadecyl-GPC

Chemical Property of 2,3-Bis(hexadecyloxy)propyl 2-(trimethylammonio)ethyl phosphate

Chemical Property:

• PSA: 86.86000
• LogP: 12.62880
• Storage Temp.: −20°C
• XLogP3: 14.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 40
• Exact Mass: 705.60362640
• Heavy Atom Count: 48
• Complexity: 681

Purity/Quality:

98%min ^*data from raw suppliers

1,2-DIHEXADECYL-RAC-GLYCERO-3-PHOSPHOCHOLINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 2,3-Bis(hexadecyloxy)propyl 2-(trimethylammonio)ethyl phosphate

There total 11 articles about 2,3-Bis(hexadecyloxy)propyl 2-(trimethylammonio)ethyl 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:

1,2-dihexadecylglycerol (6076-35-3) → 1,2-di-O-hexadecyl-3-O-<<2-(trimethylamino)ethyl>phosphoryl>-rac-glycerol (69483-37-0)

Guidance literature:

Multi-step reaction with 3 steps

1: NEt₃ / diethyl ether / 22 h / 20 - 35 °C

2: NEt₃; H₂O / diethyl ether / 2 h

3: acetonitrile; CHCl₃ / 14 h / 50 °C

With water; triethylamine; In diethyl ether; chloroform; acetonitrile; 1: Esterification / 2: Hydrolysis / 3: Amination;

DOI:10.1039/a910266n

Reference yield:

Phosphoric acid 2,3-bis-hexadecyloxy-propyl ester diphenyl ester (64599-78-6) → 1,2-di-O-hexadecyl-3-O-<<2-(trimethylamino)ethyl>phosphoryl>-rac-glycerol (69483-37-0)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂ / PtO₂ / ethyl acetate / 3000.2 Torr

2: CCl₃CN, pyridine / 48 h / 50 °C

With pyridine; hydrogen; trichloroacetonitrile; platinum(IV) oxide; In ethyl acetate;

DOI:10.1248/cpb.40.318

Reference yield:

1,2-di-O-hexadecyl-rac-glycero-3-phosphoric acid dichloride (74123-29-8) → 1,2-di-O-hexadecyl-3-O-<<2-(trimethylamino)ethyl>phosphoryl>-rac-glycerol (69483-37-0)

Guidance literature:

Multi-step reaction with 2 steps

1: Et₃N / toluene / 2 h / Ambient temperature

2: acetonitrile; propan-2-ol; H₂O / 12 h / 60 °C

With triethylamine; In water; isopropyl alcohol; toluene; acetonitrile;

DOI:10.1248/cpb.40.318

upstream raw materials:

2-bromoethylphosphoric acid dichloride

1,2-dihexadecylglycerol

trimethylamine

1,2-di-O-hexadecyl-rac-glycerol phosphoric acid

Refernces

• 1、 Akita,Umezawa,Matsukura,Oishi. "A lipid-lipase aggregate with ether linkage as a new type of immobilized enzyme for enantio-selective hydrolysis in organic solvents". . p. 318 - 324. Retrieved 2007/10/02.