1,2-Dioleoyl-sn-glycero-3-phosphoethanolamine

Base Information

• Chemical Name: 1,2-Dioleoyl-sn-glycero-3-phosphoethanolamine
• CAS No.: 4004-05-1
• Molecular Formula: C41H78NO8P
• Molecular Weight: 744.046
• Hs Code.: 29232000
• UNII: JNP6V6AI0U
• DSSTox Substance ID: DTXSID601029609
• Wikipedia: 1,2-Dioleoyl-sn-glycerophosphoethanolamine
• Wikidata: Q21079469
• Metabolomics Workbench ID: 15168
• Mol file: 4004-05-1.mol

Synonyms:1,2-dielaidoylphosphatidylethanolamine;1,2-dioleoyl-sn-glycero-3-phosphoethanolamine;1,2-dioleoylglycero-3-phosphoethanolamine;1,2-dioleoylphosphatidylethanolamine;1,2-DOPE;1-2-di-(9-octadecenoyl)-sn-glycero-3-phosphoethethanolamine;1-2-DOPE;dioleoyl cephalin;Lipofectin

Chemical Property of 1,2-Dioleoyl-sn-glycero-3-phosphoethanolamine

Chemical Property:

• Appearance/Colour: lyophilized powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 200°C(lit.)
• Refractive Index: 1.484
• Boiling Point: 759.2 °C at 760 mmHg
• PKA: 1.17±0.50(Predicted)
• Flash Point: 413 °C
• PSA: 144.19000
• Density: 1.008 g/cm³
• LogP: 12.30900
• Storage Temp.: −20°C
• XLogP3: 10.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 41
• Exact Mass: 743.54650544
• Heavy Atom Count: 51
• Complexity: 897

Purity/Quality:

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

1,2-Dioleoyl-sn-glycero-3-phosphatidylethanolamine(DOPE) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xn
• Statements: 22-38-40-48/20/22-67-36/38-20-63
• Safety Statements: 36/37-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Lipids -> Unambiguous Lipids
• Canonical SMILES: CCCCCCCCC=CCCCCCCCC(=O)OCC(COP(=O)(O)OCCN)OC(=O)CCCCCCCC=CCCCCCCCC
• Isomeric SMILES: CCCCCCCC/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(O)OCCN)OC(=O)CCCCCCC/C=C\CCCCCCCC
• Description: 1,2-Dioleoyl-sn-glycero-3-phosphoethanolamine (DOPE) is a neutral phospholipid and displays sensitivity towards pH change and has been used in the preparation of liposome and giant unilamellar vesicles (GUVs).Phosphatidylethanolamine (PE) is formed primarily in the reaction of CDP-ethanolamine and diacylglycerol. PE is one of the major components of cell membranes in bacteria and in nervous system.
• Uses: 1,2-Dioleoyl-sn-glycero-3-phosphoethanolamine (DOPE) forms heterogenous liposomes with N-[1-(2,3-dioleoyloxy)propyl]-N,N,N-trimethylammonium methylsulfate (DOTAP), which are used as delivery vehicles for therapeutic agents. 1,2-Dioleoyl-sn-glycero-3-phosphatidylethanolamine (DOPE) is a synthetic analog of naturally-occurring PE containing 18:1 fatty acids at the sn-1 and sn-2 positions. DOPE can be used as an emulsifier to facilitate DNA-liposome complex transport across membranes. It is used in combination with cationic phospholipids to increase efficiency during DNA transfection studies as a non-viral method of gene delivery. 18:1 (Δ9-Cis) PE (DOPE) has been used in the preparation of liposome for human uncoupling protein 1 (UCP1) reconstitution and for Caenorhabditis elegans autophagy related cysteine protease protein conjugation studies. It has also been used for the generation of giant unilamellar vesicles (GUVs) for septin induced deformation studies.

Technology Process of 1,2-Dioleoyl-sn-glycero-3-phosphoethanolamine

There total 17 articles about 1,2-Dioleoyl-sn-glycero-3-phosphoethanolamine 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: 90.0%

dioleoylphosphatidylcholine (4235-95-4) + ethanolamine (141-43-5) → 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (4004-05-1)

Guidance literature:

With PLD;

DOI:10.1080/10426509608545147

Reference yield:

(Z)-Octadec-9-enoic acid 2-{hydroxy-[2-(trityl-amino)-ethoxy]-phosphoryloxy}-1-((Z)-octadec-9-enoyloxymethyl)-ethyl ester (69747-56-4,71327-40-7) → dioleoylphosphatidylethanolamine (2462-63-7,4004-05-1,5683-50-1,5683-54-5,7768-07-2,16777-83-6,16810-06-3,19805-18-6)

Guidance literature:

With silica gel;

Reference yield:

1,2-dioleoylglycerol (2442-61-7,3738-74-7,22202-42-2,24529-88-2,26540-69-2,33735-55-6,38738-56-6,98719-67-6) → dioleoylphosphatidylethanolamine (2462-63-7,4004-05-1,5683-50-1,5683-54-5,7768-07-2,16777-83-6,16810-06-3,19805-18-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 1-methyl-imidazole

2: isopentyl nitrite, Py

3: 2,4,6-triisopropylbenzenesulfonyl chloride, Py

4: Zn, Py, AcOH

5: SiO₂

With pyridine; 1-methyl-1H-imidazole; 2,4,6-triisopropylphenylsulfonyl chloride; silica gel; acetic acid; zinc; isopentyl nitrite;

upstream raw materials:

1,2-dioleoyl-sn-glycerol

ethanolamine

dioleoylphosphatidylcholine

oleic anhydride

Downstream raw materials:

1,2-distearoyl-sn-glycero-3-phosphoethanolamine

C₆₁H₁₀₄NO₁₀P

Refernces

• 1、 Harris,Marshall,Lee,Siegel,Mcneilly,Yew,Nietupski,Nichols,Cherry,Wan,Jiang,Lane,Rowe,Scheule,Smith,Cheng. "The development of improved cationic lipids for gene transfer into cystic fibrosis airway epithelial cells". . p. 289 - 292. Retrieved 2007/10/03.
• 2、 Billimoria,Lewis. "The synthesis of phospholipids. I. Phosphatidyl and lysophosphatidyl ethanolamines.". . p. 1404 - 1412. Retrieved 2007/10/12.