1,2-Dioleoyl-sn-Glycero-3-Phosphocholine

Base Information

• Chemical Name: 1,2-Dioleoyl-sn-Glycero-3-Phosphocholine
• CAS No.: 4235-95-4
• Molecular Formula: C44H84NO8P
• Molecular Weight: 786.127
• Hs Code.: 29232000
• European Community (EC) Number: 224-193-8
• UNII: H026DM5V6U
• DSSTox Substance ID: DTXSID101274283
• Wikidata: Q27144815
• Metabolomics Workbench ID: 13545
• Mol file: 4235-95-4.mol

Synonyms:1,2-dioleoyl glycerophosphocholine;1,2-dioleoyl-sn-glycero-3-phosphocholine;1,2-dioleoyl-sn-glycerol-3-ethylphosphocholine;1,2-dioleoylglycerophosphocholine;1,2-DOCPC;1,2-oleoyl-sn-glycero-3-phosphocholine;1,2-oleoylphosphatidylcholine;1,2-oleoylphosphatidylcholine, (E,E)-isomer;1,2-oleoylphosphatidylcholine, (L-alpha)-(R-(Z,Z))-isomer;1,2-oleoylphosphatidylcholine, (R-(E,E))-isomer;1,2-oleoylphosphatidylcholine, (Z,Z)-(+-)-isomer;1,2-oleoylphosphatidylcholine, 14C-labeled, (R-(Z,Z))-isomer;dielaidinoyl lecithin;dielaidoylphosphatidylcholine;dioleoyl lecithin;dioleoyl phosphatidylcholine;dioleoylphosphatidylcholine;dioleoylphosphatidylcholine, DL-;dioleylphosphatidylcholine;DOPC

Chemical Property of 1,2-Dioleoyl-sn-Glycero-3-Phosphocholine

Chemical Property:

• Appearance/Colour: white solid
• Melting Point: -21 °C
• PSA: 121.00000
• LogP: 12.79440
• Storage Temp.: −20°C
• Solubility.: Chloroform (Slightly, Sonicated), Methanol (Slightly)
• XLogP3: 13.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 42
• Exact Mass: 785.59345564
• Heavy Atom Count: 54
• Complexity: 972

Purity/Quality:

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

1,2-Dioleoyl-sn-glycero-3-phosphocholine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-38-40-48/20/22-36/38-20/22-63
• Safety Statements: 36/37-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Lipids -> Unambiguous Lipids,Biological Agents -> Plant Oils and Extracts
• 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)OC[C@H](COP(=O)([O-])OCC[N+](C)(C)C)OC(=O)CCCCCCC/C=C\CCCCCCCC
• Description: DOPC, also known as 18:1 (?9-Cis) PC, is a phospholipid containing the unsaturated long-chain (18:1) oleic acid inserted at the sn-1 and sn-2 positions. It is commonly used alone, or with other components, in the generation of micelles, liposomes, and other types of artificial membranes.
• Uses: 1,2-Dioleoyl-sn-glycero-3-phosphocholine is a phospholipid containing the unsaturated long-chain (18:1) oleic acid inserted at the sn-1 and sn-2 positions. It is commonly used alone, or with other components, in the generation of micelles, liposomes, and other types of artificial membranes. 1,2-Dioleoyl-sn-glycero-3-phosphocholine has been used for the reconstitution of proteoliposome (PL). It has also been used in the preparation of lipid vesicles. 18:1 (Δ9-Cis) PC (DOPC) has been used for reproducing the supramolecular structure of the synovial fluid. It may also be used in the liposome preparation and in the preparation of planar supported membranes.

Technology Process of 1,2-Dioleoyl-sn-Glycero-3-Phosphocholine

There total 14 articles about 1,2-Dioleoyl-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: 90.3%

cis-Octadecenoic acid (112-80-1,2027-47-6) + L-glycero-3-phosphorylcholine (28319-77-9,563-24-6) → dioleoylphosphatidylcholine (4235-95-4)

Guidance literature:

With dmap; Hyflo Super-Cel; dicyclohexyl-carbodiimide; In chloroform; at 30 ℃;

DOI:10.1016/j.chemphyslip.2005.06.001

Reference yield: 80.0%

choline (62-49-7) + 1,2-dioleoyl-sn-glycero-3-phosphate sodium salt (108392-02-5) → dioleoylphosphatidylcholine (4235-95-4)

Guidance literature:

DOI:10.1080/10426509608545147

Reference yield: 64.0%

2-(1',2'-dioleoyl-sn-glycero)-2-oxo-1,3,2-dioxaphospholane + trimethylamine (75-50-3) → dioleoylphosphatidylcholine (4235-95-4)

Guidance literature:

With triethylamine; In acetonitrile; at 20 ℃; for 16h;

DOI:10.1021/jo990414e

upstream raw materials:

(Z)-9-octadecenoyl chloride

L-glycero-3-phosphorylcholine

oleic anhydride

choline tosylate

Downstream raw materials:

1,2-dioleoyl-sn-glycero-3-[phospho-rac-(1-glycerol)]

1,2-dioleoyl-sn-glycero-3-phosphocholine

1-oleoyl-L-lysophosphatidylcholine

2-(octadec-cis-9-enoyl)-sn-glycero-3-phosphocholine

Refernces

• 1、 -. "Preparation method of dioleoyl phosphatidylcholine". Paragraph 0030-0046. . Retrieved 2020/08/07.
• 2、 Roodsari, Farzaneh S.,Wu, Dongpei,Pum, Gregory S.,Hajdu, Joseph. "A new approach to the stereospecific synthesis of phospholipids. The use of L-glyceric acid for the preparation of diacylglycerols, phosphatidylcholines, and related derivatives". . p. 7727 - 7737. Retrieved 2007/10/03.