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

Melting point:

200°C(lit.)

Boiling point:

759.2±70.0 °C(Predicted)

Density 

1.008±0.06 g/cm3(Predicted)

storage temp. 

-20°C

solubility 

DMSO: 31.25 mg/mL (42.00 mM)

pka

1.17±0.50(Predicted)

form 

lyophilized powder

color 

White to Light yellow

BRN 

1718431

InChIKey

MWRBNPKJOOWZPW-XFBMKQTANA-N

SMILES

[C@H](COP(O)(=O)OCCN)(COC(=O)CCCCCCC/C=C\CCCCCCCC)OC(=O)CCCCCCC/C=C\CCCCCCCC |&1:0,r|

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-38-40-48/20/22-67-36/38-20-63

Safety Statements 

36/37-26

RIDADR 

UN 1888 6.1/PG 3

WGK Germany 

3

F 

8-10-23

HS Code 

29232000

MSDS

• Language:English Provider:SigmaAldrich

1,2-Dioleoyl-sn-glycero-3-phosphoethanolamine Usage And Synthesis

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.

Chemical Properties

Yellowish wax

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.

Uses

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.

Uses

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.

Definition

ChEBI: Dioleoyl phosphatidylethanolamine is a phosphatidylethanolamine in which the phosphatidyl acyl groups are both oleoyl.

General Description

1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (18:1 (Δ9-Cis) PE (DOPE)) is a neutral phospholipid and displays sensitivity towards pH change. At acidic it is an inverted hexagonal micelle and transforms to spherical micelle at alkaline pH.

Biological Activity

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).

Biochem/physiol Actions

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).

storage

Store at -20°C

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