1,2-Dilinoleoyl-SN-glycero-3-phosphocholine

Base Information

• Chemical Name: 1,2-Dilinoleoyl-SN-glycero-3-phosphocholine
• CAS No.: 998-06-1
• Molecular Formula: C44H80 N O8 P
• Molecular Weight: 782.095
• Hs Code.: 2923200000
• European Community (EC) Number: 213-647-0
• UNII: 7L874P1M1O
• DSSTox Substance ID: DTXSID201260902
• Metabolomics Workbench ID: 13567
• Mol file: 998-06-1.mol

Synonyms:1,2-dilinoleoyl-3-glycerophosphocholine;1,2-linoleoyl-sn-glycero-3-phosphocholine;1,2-linoleoylphosphatidylcholine;1,2-linoleoylphosphatidylcholine, (R-(all Z))-isomer;1,2-linoleoylphosphatidylcholine, 14C-labeled cpd, (R-(all Z))-isomer;dilinoleoyl phosphatidylcholine;dilinoleoyllecithin;dilinoleoylphosphatidylcholine;DLPC lipid

Chemical Property of 1,2-Dilinoleoyl-SN-glycero-3-phosphocholine

Chemical Property:

• Appearance/Colour: lyophilized powder
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 121.00000
• Density: g/cm³
• LogP: 12.34640
• Storage Temp.: −20°C
• XLogP3: 12.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 40
• Exact Mass: 781.56215551
• Heavy Atom Count: 54
• Complexity: 1060

Purity/Quality:

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

1,2-Dilinoleoyl-sn-glycero-3-phosphocholine ≥99% (TLC), lyophilized powder ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Lipids -> Unambiguous Lipids
• Canonical SMILES: CCCCCC=CCC=CCCCCCCCC(=O)OCC(COP(=O)([O-])OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCC=CCCCCC
• Isomeric SMILES: CCCCC/C=C\C/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)([O-])OCC[N+](C)(C)C)OC(=O)CCCCCCC/C=C\C/C=C\CCCCC
• Uses: 18:2 (Cis) PC (DLPC) has been used for liposome preparation.

Technology Process of 1,2-Dilinoleoyl-SN-glycero-3-phosphocholine

There total 6 articles about 1,2-Dilinoleoyl-SN-glycero-3-phosphocholine 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: 84.0%

linoleic acid (60-33-3,116745-32-5,26085-09-6,64080-88-2,7049-66-3,949900-18-9,60476-23-5,6144-28-1,67922-65-0,89718-18-3) + sn-glycero-3-phosphocholine cadmium chloride complex → (R)-2,3-bis(((9Z,12Z)-octadeca-9,12-dienoyl)oxy)propyl (2-(trimethylammonio)ethyl) phosphate (998-06-1)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃; for 40h; Inert atmosphere;

DOI:10.1071/CH12404

Reference yield:

1-α-glycerophosphocholine cadmium chloride salt + linoleic acid (60-33-3,116745-32-5,26085-09-6,64080-88-2,7049-66-3,949900-18-9,60476-23-5,6144-28-1,67922-65-0,89718-18-3) → (R)-2,3-bis(((9Z,12Z)-octadeca-9,12-dienoyl)oxy)propyl (2-(trimethylammonio)ethyl) phosphate (998-06-1)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃; for 40h;

DOI:10.1071/CH14606

Reference yield:

linoleyl chloride (7459-33-8) + 2C8H20NO6P*CdCl2 → (R)-2,3-bis(((9Z,12Z)-octadeca-9,12-dienoyl)oxy)propyl (2-(trimethylammonio)ethyl) phosphate (998-06-1)

Guidance literature:

With pyridine; In chloroform;

upstream raw materials:

linoleyl chloride

choline chloride

(2S)-1-hydroxy-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propan-2-yl-(9Z,12Z)-octadeca-9,12-dienoate

(S)-(+)-(2,2-dimethyl-[1,3]dioxolan-4-yl)methanol

Downstream raw materials:

L-γ-linoleoyl-α-lysolecithin

(R,S)-coriolic acid

(10E,12Z)-9-hydroxy-10,12-octadecadienoic acid

9-Hode

Refernces

• 1、 Niezgoda, Natalia,Gliszczyńska, Anna,G?adkowski, Witold,Kempińska, Katarzyna,Wietrzyk, Joanna,Wawrzeńczyk, Czes?aw. "Phosphatidylcholine with cis-9,trans-11 and trans-10,cis-12 Conjugated Linoleic Acid Isomers: Synthesis and Cytotoxic Studies". . p. 1065 - 1075. Retrieved 2016/01/15.
• 2、 Baba, Naomichi,Akiyama, Takeshi,Tahara, Shoichi,Nakajima, Shuhei. "Short-route Synthesis of a Glycerophospholipid Bearing an Unsaturated Acyl Group at the sn-1 Position". . p. 353 - 354. Retrieved 2007/10/02.