2-[2,3-bis[[(E)-octadec-9-enoyl]oxy]propoxy-hydroxyphosphoryl]oxyethyl-trimethylazanium

Base Information

• Chemical Name: 2-[2,3-bis[[(E)-octadec-9-enoyl]oxy]propoxy-hydroxyphosphoryl]oxyethyl-trimethylazanium
• CAS No.: 56782-46-8
• Molecular Formula: C₄₄H₈₄NO₈P
• Molecular Weight: 786.127
• European Community (EC) Number: 637-214-4
• Nikkaji Number: J2.012.319B
• ChEMBL ID: CHEMBL4081726
• Mol file: 56782-46-8.mol

Synonyms:56782-46-8;1,2-Di[trans-9-octadecenoyl]-sn-glycero-3-phosphocholine;trimethyl(2-{[3-[octadec-11-enoyloxy]-2-[octadec-9-enoyloxy]propyl phosphonato]oxy}ethyl)azanium;2-[2,3-bis[[(E)-octadec-9-enoyl]oxy]propoxy-hydroxyphosphoryl]oxyethyl-trimethylazanium;CHEMBL4081726;SCHEMBL20494173;1,2-Dielaidoyl-sn-glycero-3-phosphocholine, >=98% (GLC, TLC);2-[[[2,3-Bis[(1-oxo-9-octadecenyl)oxy]propoxy]phosphonyl]oxy]ethyltrimethylaminium

Chemical Property of 2-[2,3-bis[[(E)-octadec-9-enoyl]oxy]propoxy-hydroxyphosphoryl]oxyethyl-trimethylazanium

Chemical Property:

• PSA: 121.00000
• LogP: 12.79440
• Storage Temp.: −20°C
• XLogP3: 13.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 42
• Exact Mass: 786.60128067
• Heavy Atom Count: 54
• Complexity: 980

Purity/Quality:

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

1,2-DI-ELAIDOYL-SN-GLYCERO-3-PHOSPHOCHOLINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCC=CCCCCCCCC(=O)OCC(COP(=O)(O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC
• Isomeric SMILES: CCCCCCCC/C=C/CCCCCCCC(=O)OCC(COP(=O)(O)OCC[N+](C)(C)C)OC(=O)CCCCCCC/C=C/CCCCCCCC
• Uses: 18:1 (Δ9-Trans) PC is suitable for use as a synthetic lipid to study its effects on sarcoplasmic reticulum (SR) Ca2+-ATPase (SERCA) activity.

Technology Process of 2-[2,3-bis[[(E)-octadec-9-enoyl]oxy]propoxy-hydroxyphosphoryl]oxyethyl-trimethylazanium

There total 2 articles about 2-[2,3-bis[[(E)-octadec-9-enoyl]oxy]propoxy-hydroxyphosphoryl]oxyethyl-trimethylazanium 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:

dioleoylphosphatidylcholine (4235-95-4) → 1,2-dioleoyl-sn-glycero-3-phosphocholine (4235-95-4,7768-08-3,10015-85-7,52088-89-8,56648-95-4,68737-67-7,74493-34-8,84366-67-6,56782-46-8)

Guidance literature:

With azobis(dimethylvaleronitrile); 2-hydroxyethanethiol; In tert-butyl alcohol; at 54 ℃; for 4h; Further Variations:; Reagents; Temperatures; Reaction partners; Product distribution;

DOI:10.1021/ja994169s

Reference yield:

L-glycero-3-phosphorylcholine (28319-77-9,563-24-6) + Tras-Elaidate sodium salt (18175-45-6) → 1,2-dioleoyl-sn-glycero-3-phosphocholine (4235-95-4,7768-08-3,10015-85-7,52088-89-8,56648-95-4,68737-67-7,74493-34-8,84366-67-6,56782-46-8)

Guidance literature:

DOI:10.1021/ja00422a003

Reference yield: 66.0%

L-homoserine (672-15-1,119736-88-8) + 1,2-dioleoyl-sn-glycero-3-phosphocholine (4235-95-4,7768-08-3,10015-85-7,52088-89-8,56648-95-4,68737-67-7,74493-34-8,84366-67-6,56782-46-8) → choline (62-49-7) + (E)-Octadec-9-enoic acid (R)-2-[((S)-3-amino-3-carboxy-propoxy)-hydroxy-phosphoryloxy]-1-((E)-octadec-9-enoyloxymethyl)-ethyl ester (108824-18-6,119067-15-1)

Guidance literature:

With acetate buffer; phospholipase D; In chloroform; water; at 45 ℃; for 2h;

DOI:10.1248/cpb.35.447

upstream raw materials:

L-glycero-3-phosphorylcholine

Tras-Elaidate sodium salt

dioleoylphosphatidylcholine

Downstream raw materials:

choline

(E)-Octadec-9-enoic acid (R)-2-[((S)-3-amino-3-carboxy-propoxy)-hydroxy-phosphoryloxy]-1-((E)-octadec-9-enoyloxymethyl)-ethyl ester

Refernces