(2-aminoethoxy)[(2R)-2,3-bis(octadec-9-enoyloxy)propoxy]phosphinic acid

• ChemBase ID: 154493
• Molecular Formular: C41H78NO8P
• Molecular Mass: 744.033681
• Monoisotopic Mass: 743.54650509
• SMILES: CCCCCCCC/C=C/CCCCCCCC(=O)OC[C@H](COP(=O)(O)OCCN)OC(=O)CCCCCCC/C=C/CCCCCCCC
• Canonical SMILES: CCCCCCCC/C=C/CCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCC/C=C/CCCCCCCC)COP(=O)(OCCN)O
• InChI: InChI=1S/C41H78NO8P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-40(43)47-37-39(38-49-51(45,46)48-36-35-42)50-41(44)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h17-20,39H,3-16,21-38,42H2,1-2H3,(H,45,46)/t39-/m1/s1
• InChIKey: MWRBNPKJOOWZPW-LDLOPFEMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2-aminoethoxy)[(2R)-2,3-bis(octadec-9-enoyloxy)propoxy]phosphinic acid; (2-aminoethoxy)[(2R)-2,3-bis[(9E)-octadec-9-enoyloxy]propoxy]phosphinic acid
• IUPAC Traditional name: 2-aminoethoxy(2R)-2,3-bis(octadec-9-enoyloxy)propoxyphosphinic acid; 1,2-dielaidoyl-sn-gl
• Synonyms: 1,2-Dioleoyl-sn-glycero-3-phosphoethanolamine; L-α-Phosphatidylethanolamine, dioleoyl; (9Z)-9-Octadecenoic acid (1R)-1-[[[(2-aminoethoxy)hydroxyphosphinyl]oxy]methyl]-1,2-ethanediyl ester; 1,2-Di(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine; 3-sn-Phosphatidylethanolamine, 1,2-dideoyl; L-β,γ-Dioleoyl-α-cephalin; DOPE; Dioleoyl phosphatidylethanolamine; PE(18:1(9Z)/18:1(9Z)); 1,2-Dioleoyl-sn-glycero-3-phosphoethanolamine; 1,2-二油酰-sn-甘油-3-磷酸乙醇胺; 二油酰基 L-α-磷脂酰乙醇胺; 1,2-二油酰-sn-甘油-3-磷酸乙醇胺

Database IDs

• CAS Number: 4004-05-1
• EC Number: 200-663-8
• MDL Number: MFCD00057986
• Beilstein Number: 1718431
• PubChem SID: 162248632; 24898174; 24866597; 24878438
• PubChem CID: 9546744

CALCULATED PROPERTIES

• Acid pKa: 1.8688003
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 11.505306
• LogD (pH = 7.4): 11.504376
• Log P: 11.505346
• Molar Refractivity: 211.6411 cm^3
• Polarizability: 83.91477 Å^3
• Polar Surface Area: 134.38 Å^2
• Rotatable Bonds: 41
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: lyophilized powder

Safety Information

• European Hazard Symbols: Harmful (Xn)
• UN Number: 1888
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 22-38-40-48/20/22
• Safety Statements: 36/37
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H315-H351-H373
• GHS Precautionary statements: P281
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US); Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• RID/ADR: UN 1888 6.1/PG 3
• Storage Temperature: -20°C

Product Information

• Purity: ≥97.0% (TLC); ≥98% (TLC); ≥98.0% (TLC); ≥99% (GC); ≥99.0% (10 mg phospholipid per ml CHCl3, TLC)
• Biological Source: from synthetic
• Empirical Formula (Hill Notation): C41H78NO8P
• Classification: Genuine Natural Compounds

DETAILS

Sigma Aldrich - 54008

Application
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.

Sigma Aldrich - P1223

Application
Forms liposomes with DC-cholesterol that can be used to efficiently transfect several mammalian cell lines.
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.
Packaging
Packaged under Argon.

Sigma Aldrich - 42490

Application
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.

Sigma Aldrich - 76548

Application
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.
Biochem/physiol Actions
DOPE in mixed membranes have been found to decrease fluorescence lifetime and increase acyl-chain order.2 DOPE is an essential component of cationic liposomes designed to deliver DNA into gliosarcoma3 and kidney4 cell lines (gene therapy).