1,2-Dioleoyl-sn-glycero-3-phosphoethanolamine （DOPE） - ≥98% , CAS No.4004-05-1

CAS: 4004-05-1 Cat. No.: D155634 Molecular Weight: 744.05

GRADE & PURITY ≥98%

Synonyms

GPEtn(18:1w9/18:1w9) | 1,2-Dioleoyl-sn-gl | AMY10805 | DOPE, l- | SCHEMBL25038 | Ethanol, 2-amino-, dihydrogen phosphate (ester), monoester with 1,2-diolein, L- | 1,2-Dioleoyl-sn-glycero-3-phosphoethanolamine | AS-74734 | PE(18:1/18:1) | 1,2-dioleoyl-sn-g

Storage

Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

Overview

Application

DOPE in mixed membranes have been found to decrease fluorescence lifetime and increase acyl-chain order. DOPE is an essential component of cationic liposomes designed to deliver DNA into gliosarcoma and kidney cell lines (gene therapy).
1,2-Dioleoyl-tin-glycerol-3-phosphate ethanolamine (DOPE) forms heterogeneous liposomes with N-[1-(2,3-dioleoyloxy)propyl]-N,N,N-trimethylammonium sulfate (DOTAP) as a drug delivery carrier for therapeutics. It also forms liposomes with DC-cholesterol (which can be used to effectively transfect several mammalian cell lines).

Specifications

Synonyms

GPEtn(18:1w9/18:1w9) | 1, 2-Dioleoyl-sn-gl | AMY10805 | DOPE, l- | SCHEMBL25038 | Ethanol, 2-amino-, dihydrogen phosphate (ester), monoester with 1, 2-diolein, L- | 1, 2-Dioleoyl-sn-glycero-3-phosphoethanolamine | AS-74734 | PE(18:1/18:1) | 1, 2-dioleoyl-sn-g

Specifications & Purity

≥98%

Biochemical and Physiological Mechanisms

It has been found that DOPE in the mixed film reduces the fluorescence lifetime and increases the acyl chain sequence. DOPE is an important component of cationic liposomes, specifically designed to deliver DNA to glioblastoma and kidney cell lines (gene t

Storage

Store at -20°C, Argon charged

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 504764803
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504764803
• Canonical Smiles: CCCCCCCCC=CCCCCCCCC(=O)OCC(COP(=O)(O)OCCN)OC(=O)CCCCCCCC=CCCCCCCCC
• IUPAC Name: [(2R)-3-[2-aminoethoxy(hydroxy)phosphoryl]oxy-2-[(Z)-octadec-9-enoyl]oxypropyl] (Z)-octadec-9-enoate
• InChIKey: MWRBNPKJOOWZPW-NYVOMTAGSA-N
• 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)/b19-17-,20-18-/t39-/m1/s1
• Isomeric SMILES: CCCCCCCC/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(O)OCCN)OC(=O)CCCCCCC/C=C\CCCCCCCC
• Molecular Weight: 744.05
• Reaxy-Rn: 2343401
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=2343401&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Glycerophospholipids
      • Subclass Glycerophosphoethanolamines

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Glycerophospholipids
• Subclass: Glycerophosphoethanolamines
• Intermediate Tree Nodes: Not available
• Direct Parent: Phosphatidylethanolamines
• Alternative Parents: Phosphoethanolamines Fatty acid esters Dialkyl phosphates Dicarboxylic acids and derivatives Carboxylic acid esters Amino acids and derivatives Organopnictogen compounds Organic oxides Monoalkylamines Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Diacylglycero-3-phosphoethanolamine - Phosphoethanolamine - Fatty acid ester - Dialkyl phosphate - Dicarboxylic acid or derivatives - Organic phosphoric acid derivative - Phosphoric acid ester - Alkyl phosphate - Fatty acyl - Amino acid or derivatives - Carboxylic acid ester - Carboxylic acid derivative - Organopnictogen compound - Organic oxygen compound - Organooxygen compound - Organonitrogen compound - Amine - Primary aliphatic amine - Organic nitrogen compound - Primary amine - Carbonyl group - Organic oxide - Hydrocarbon derivative - Aliphatic acyclic compound
• Description: This compound belongs to the class of organic compounds known as phosphatidylethanolamines. These are glycerophosphoetahnolamines in which two fatty acids are bonded to the glycerol moiety through ester linkages.
• External Descriptors: Diacylglycerophosphoethanolamines

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Sensitivity: light & air & heat & Moisture sensitive
• Specific Rotation[α]: +5.0 to +7.0 deg(C=2, CHCl3)
• Melt Point(°C): 200°C(lit.)
• Molecular Weight: 744.000 g/mol
• XLogP3: 10.600
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 41
• Exact Mass: 743.547 Da
• Monoisotopic Mass: 743.547 Da
• Topological Polar Surface Area: 134.000 Ų
• Heavy Atom Count: 51
• Formal Charge: 0
• Complexity: 897.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 1
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 2
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 2
• Covalently-Bonded Unit Count: 1

References

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