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Merck

42490

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

≥99.0% (10 mg phospholipid per ml CHCl3, TLC)

Synonym(s):

(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))

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About This Item

Empirical Formula (Hill Notation):
C41H78NO8P
CAS Number:
4004-05-1
Molecular Weight:
744.03
UNSPSC Code:
12352211
NACRES:
NA.25
PubChem Substance ID:
57650115
EC Number:
200-663-8
Beilstein/REAXYS Number:
1718431
MDL number:
MFCD00057986

Key Documents

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Product Name

1,2-Dioleoyl-sn-glycero-3-phosphoethanolamine, ≥99.0% (10 mg phospholipid per ml CHCl3, TLC)

InChI key

MWRBNPKJOOWZPW-CLFAGFIQSA-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-

SMILES string

CCCCCCCC\C=C/CCCCCCCC(=O)OCC(COP(O)(=O)OCCN)OC(=O)CCCCCCC\C=C/CCCCCCCC

assay

≥99.0% (10 mg phospholipid per ml CHCl3, TLC)

form

liquid

functional group

phospholipid

lipid type

phosphoglycerides

storage temp.

−20°C

Quality Level

100

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Related Categories

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 .

pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

signalword

Danger

Hazard Classifications

Acute Tox. 3 Inhalation - Acute Tox. 4 Oral - Aquatic Chronic 3 - Carc. 2 - Eye Irrit. 2 - Repr. 2 - Skin Irrit. 2 - STOT RE 1 - STOT SE 3

target_organs

Central nervous system, Liver,Kidney

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCJ6871
BCCB6052
BCBV0250
BCBM1838V
BCBJ3088V

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Antonio A M Gasperini et al.
Langmuir : the ACS journal of surfaces and colloids, 31(11), 3308-3317 (2015-03-03)
This work presents a study of the association between low molecular weight hyaluronic acid (16 kDa HA) and cationic liposomes composed of egg phosphatidylcholine (EPC), 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (DOPE), and 1,2-dioleoyl-3-trimethylammonium-propane (DOTAP). The cationic liposome/HA complexes were evaluated to determine their mesoscopic
Michael Ablinger et al.
International journal of molecular sciences, 22(7) (2021-04-04)
Intermediate junctional epidermolysis bullosa caused by mutations in the COL17A1 gene is characterized by the frequent development of blisters and erosions on the skin and mucous membranes. The rarity of the disease and the heterogeneity of the underlying mutations renders
Timo Löser et al.
Cells, 10(10) (2021-10-24)
Mitochondria are ubiquitous organelles of eukaryotic organisms with a number of essential functions, including synthesis of iron-sulfur clusters, amino acids, lipids, and adenosine triphosphate (ATP). During aging of the fungal aging model Podospora anserina, the inner mitochondrial membrane (IMM) undergoes
Ryo Furukawa et al.
Biomaterials, 57, 107-115 (2015-04-29)
Mitochondrial genome-targeting nucleic acids are promising therapeutic candidates for treating mitochondrial diseases. To date, a number of systems for delivering genetic information to the cytosol and the nucleus have been reported, and several successful gene therapies involving gene delivery targeted
Jonathan Langdown et al.
Blood, 124(12), 1951-1956 (2014-07-23)
In this study, we describe a novel thrombomodulin (TM) mutation (c.1611C>A) that codes for a change from cysteine 537 to a premature stop codon (p.Cys537Stop). Three members of a family with a history of posttraumatic bleeding were identified to be
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