4004-05-1

Basic information

• Product Name: 1,2-DIOLEOYL-SN-GLYCERO-3-PHOSPHOETHANOLAMINE
• Synonyms: 3-SN-PHOSPHATIDYLETHANOLAMINE, 1,2-DIDEOYL;1,2-DIOLEOYL-SN-GLYCERO-3-PHOSPHOETHANOLAMINE;1,2-DI([CIS]-9-OCTADECENOYL)-SN-GLYCERO-3-PHOSPHOETHANOLAMINE;18:1 PE;L-ALPHA-PHOSPHATIDYLETHANOLAMINE, DIOLEOYL;L-ALPHA-PHOSPHATIDYLETHANOLAMINE, DIOLEOYL (C18:1,[CIS]-9);L-BETA,GAMMA-DIOLEOYL-ALPHA-CEPHALIN;DIOLEOYL PHOSPHATIDYL ETHANOLAMINE
• CAS NO: 4004-05-1
• Molecular Formula: C₄₁H₇₈NO₈P
• Molecular Weight: 744.03
• EINECS: 200-663-8
• Mol File: 4004-05-1.mol

Chemical Properties

• Melting Point: 200°C(lit.)
• Boiling Point: 759.2 °C at 760 mmHg
• Flash Point: 413 °C
• Appearance: /lyophilized powder
• Density: 1.008 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.484
• Storage Temp.: −20°C
• PKA: 1.17±0.50(Predicted)
• BRN: 1718431
• CAS DataBase Reference: 1,2-DIOLEOYL-SN-GLYCERO-3-PHOSPHOETHANOLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-DIOLEOYL-SN-GLYCERO-3-PHOSPHOETHANOLAMINE(4004-05-1)
• EPA Substance Registry System: 1,2-DIOLEOYL-SN-GLYCERO-3-PHOSPHOETHANOLAMINE(4004-05-1)

Safety Data

• Hazard Codes: Xn
• 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
• Hazardous Substances Data: 4004-05-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Applications:
1,2-Dioleoyl-sn-glycero-3-phosphoethanolamine (DOPE) is used as a component in the formation of heterogeneous liposomes with N-[1-(2,3-dioleoyloxy)propyl]-N,N,N-trimethylammonium methylsulfate (DOTAP). These liposomes serve as delivery vehicles for therapeutic agents, enhancing the efficiency of drug administration.
Used in Gene Delivery:
DOPE is used as an emulsifier to facilitate the transport of DNA-liposome complexes across membranes. It is often used in combination with cationic phospholipids to increase the efficiency of DNA transfection studies, providing a non-viral method of gene delivery.
Used in Biomedical Research:
DOPE has been utilized in the preparation of liposomes for various research applications, such as the reconstitution of human uncoupling protein 1 (UCP1) and the conjugation of Caenorhabditis elegans autophagy-related cysteine protease proteins. Additionally, it has been used in the generation of giant unilamellar vesicles (GUVs) for studying septin-induced deformation.
Used in the Preparation of Liposomes and Giant Unilamellar Vesicles (GUVs):
DOPE is employed in the preparation of liposomes and GUVs due to its ability to form different structures based on pH changes, making it a versatile component in the study of membrane biophysics and the development of novel drug delivery systems.

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).

InChI:InChI=1/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

Synthetic route

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

Conditions	Yield
With PLD transesterification;	90%

L-1,2-Di-O-oleoyl-glycerin-3-phosphorsaeurebenzylester-<2-triphenylmethylamino-ethylester> → 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (4004-05-1)

Conditions	Yield
(i) NaI, (ii) aq. AcOH; Multistep reaction;

1,2-dioleoyl-sn-glycerol (24529-88-2) + ethanolamine (141-43-5) → 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (4004-05-1)

Conditions	Yield
With triethylamine; trichlorophosphate 1) THF, a) 0 deg C, 1 h, b) room temp., 3 h, 2) THF, a) 0 deg C, 4 h, b) room temp., 8 h; Yield given. Multistep reaction;

sodium-salt of phosphoric acid-<(R)-1,2-bis-oleoyloxy-propyl ester>-<2-phthalimido-ethyl ester> → 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (4004-05-1)

Conditions	Yield
With hydrazine hydrate

oleic anhydride (6085-36-5, 55726-25-5, 24909-72-6) → 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (4004-05-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: 66 percent 2: 80 percent 3: 90 percent / PLD View Scheme

1,2-dioleoyl-sn-glycero-3-phosphate sodium salt (108392-02-5) → 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (4004-05-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 80 percent 2: 90 percent / PLD View Scheme

(S)-3-(3,4-Dimethoxybenzyloxy)propane-1,2-diyl Dioleate (139115-88-1) → 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (4004-05-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 84 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) / CH2Cl2; H2O / 2 h 2: 1) Et3N, POCl3, 2) Et3N / 1) THF, a) 0 deg C, 1 h, b) room temp., 3 h, 2) THF, a) 0 deg C, 4 h, b) room temp., 8 h View Scheme

L-1,2-Di-O-oleoyl-glycerin-3-phosphorsaeure-dibenzylester (19805-13-1) → 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (4004-05-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: (i) NaI, (ii) AgNO3 2: benzene 3: (i) NaI, (ii) aq. AcOH View Scheme

L-1,2-Di-O-oleoyl-glycerin-3-phosphorsaeurebenzylester-silbersalz → 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (4004-05-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: benzene 2: (i) NaI, (ii) aq. AcOH View Scheme

1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (4004-05-1) + 3-propionic acid (80028-35-9) → C50H88N3O9P

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane; N,N-dimethyl-formamide at 20℃; Inert atmosphere;	100%

1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (4004-05-1) + N2-[N2,N6-bis(tert-butoxycarbonyl)-L-lysyl]-N6-(tert-butoxycarbonyl)-L-lysine (45315-76-2) → C68H126N5O16P

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane; N,N-dimethyl-formamide at 20℃; Inert atmosphere;	97%

1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (4004-05-1) + N-hydroxysuccinimidyl ester 3-methyl-3-(2,4,5-trimethyl-3,6-dioxocyclo-hexa-1,4-dienyl) butanoic acid (121030-88-4) → C55H94NO11P (1073588-75-6)

Conditions	Yield
With triethylamine In dichloromethane at 0℃; Inert atmosphere;	96%

1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (4004-05-1) + Propiolic acid (471-25-0) → 1,2-dioleoyl-sn-glycero-3-phosphoethanoloamine-N-prop-2'-ynamide (910227-37-1)

Conditions	Yield
With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at 20℃; for 40h;	95%

1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (4004-05-1) + hexanedioic acid bis(N-hydroxysuccinimide ester) (59156-70-6) → DOPE-Ad-ONSu (930280-91-4)

Conditions	Yield
With triethylamine In chloroform; N,N-dimethyl-formamide at 20℃; for 2h;	95%
In chloroform; N,N-dimethyl-formamide
In chloroform; N,N-dimethyl-formamide

1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (4004-05-1) + 3-(1-(1-(4-((6-amino-8-hydroxy-2-(2-methoxyethoxy)-9H-purin-9-yl)methyl)phenyl)-1-oxo-5,8,11,14,17,20,23,26,29,32-decaoxa-2-azatetratriacontan-34-yl)-1H-1,2,3-triazol-4-yl)propanoic acid (1149339-80-9) → 2-(3-(1-(1-(4-((6-amino-8-hydroxy-2-(2-methoxyethoxy)-9H-purin-9-yl)methyl)phenyl)-1-oxo-5,8,11,14,17,20,23,26,29,32-decaoxa-2-azatetratriacontan-34-yl)-1H-1,2,3-triazole-4-yl)propanamido)ethyl 2,3-bis(oleoyloxy)propyl phosphate

Conditions	Yield
With 2-(1H-9-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluroniumhexafluorophosphate; triethylamine In dichloromethane; N,N-dimethyl-formamide at 20℃;	92%

1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (4004-05-1) + 3-(2'-acetoxy-4',6'-dimethylphenyl)-3,3-dimethylpropanoic acid (134098-68-3) → C56H96NO11P

Conditions	Yield
Stage #1: 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine; 3-(2'-acetoxy-4',6'-dimethylphenyl)-3,3-dimethylpropanoic acid With benzotriazol-1-ol In N,N-dimethyl-formamide at 0℃; for 0.0833333h; Inert atmosphere; Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 5h; Inert atmosphere;	92%

1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (4004-05-1) + 4-{[6-amino-2-(2-methoxyethoxy)-8-oxo-7H-purine-9(8H)-yl]methyl}benzoic acid (1062444-54-5) → (2R)‑3‑(((2‑(4‑((6‑amino‑2‑(2‑methoxyethoxy)‑8‑oxo‑7,8‑dihydro‑9H-purin‑9‑yl)methyl)benzamido)ethoxy)(hydroxy)phosphoryl)oxy)propane‑1,2‑diyldioleate

Conditions	Yield
With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane; N,N-dimethyl-formamide	79%
Stage #1: 4-{[6-amino-2-(2-methoxyethoxy)-8-oxo-7H-purine-9(8H)-yl]methyl}benzoic acid With triethylamine; HATU In N,N-dimethyl-formamide at 20℃; for 0.25h; Inert atmosphere; Stage #2: 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine In dichloromethane; N,N-dimethyl-formamide for 12h; Solvent; Reagent/catalyst;

1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (4004-05-1) + fluoresceinyl 5-isothiocyanate (1173-43-9) → C62H89N2O13PS

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; Inert atmosphere;	79%

3-(2-((bis(benzyloxy)phosphoryl)oxy)-4,6-dimethylphenyl)-3-methylbutanoic acid (153910-64-6) + 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (4004-05-1) → (2R)-3-(((2-(3-(2-((bis(benzyloxy)phosphoryl)oxy)-4,6-dimethylphenyl)-3-methylbutanamido)ethoxy)(hydroxy)phosphoryl)oxy)propane-1,2-diyl dioleate

Conditions	Yield
Stage #1: 3-(2-((bis(benzyloxy)phosphoryl)oxy)-4,6-dimethylphenyl)-3-methylbutanoic acid; 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine With benzotriazol-1-ol In N,N-dimethyl-formamide at 0℃; for 0.0833333h; Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide	77%

1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (4004-05-1) + C16H17NO6 (1073493-61-4) → C53H90NO11P (1073588-74-5)

Conditions	Yield
With triethylamine In dichloromethane at 0℃; Inert atmosphere;	75%

1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (4004-05-1) + N-(tert-butoxycarbonyl)-4-aminobutanoic acid (57294-38-9) → C50H93N2O11P

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In chloroform; N,N-dimethyl-formamide at 20℃; Inert atmosphere;	64%

1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (4004-05-1) + 5-(((2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-yl)oxy)-5-oxopentanoic acid (1415981-75-7) → (Z)-(2R)-3-(((2-(5-(((2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-yl)oxy)-5-oxopentanamido)ethoxy)(hydroxy)phosphoryl)oxy)propane-1,2-diyl dioleate (1415981-76-8)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In chloroform; N,N-dimethyl-formamide at 20℃; Inert atmosphere;	61%

1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (4004-05-1) + (1R,8S,9ξ)-bicyclo[6.1.0]non-4-yn-9-ylmethyl (4-nitrophenyl) carbonate → (2R)-3-(((2-(((((1R,8S,9s)-bicyclo[6.1.0]non-4-yn-9-yl)methoxy)carbonyl)amino)ethoxy)(hydroxy)phosphoryl)oxy)propane-1,2-diyl dioleate

Conditions	Yield
With triethylamine In tetrahydrofuran; N,N-dimethyl-formamide at 60℃; for 6h;	60%

1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (4004-05-1) + 4-{[6-amino-2-(2-methoxyethoxy)-8-oxo-7H-purine-9(8H)-yl]methyl}benzoic acid (1062444-54-5) → 2-(4-((6-amino-2-(2-methoxyethoxy)-8-oxo-7H-purin-9(8H)-yl)methyl)benzamido)ethyl 2,3-bis(oleoyloxy)propyl phosphate (1346265-99-3)

Conditions	Yield
With 2-(1H-9-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluroniumhexafluorophosphate; triethylamine In dichloromethane; N,N-dimethyl-formamide at 20℃;	58%

2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetic acid + 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (4004-05-1) → (2R)-3-((hydroxy(2-(2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetamido)ethoxy)phosphoryl)oxy)propane-1,2-diyl dioleate

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In chloroform; N,N-dimethyl-formamide at 0 - 20℃; for 6h; Inert atmosphere;	55%

1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (4004-05-1) + 4-methoxybenzoic acid (100-09-4) → DOPE-Anisamide

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 24h; Inert atmosphere; Darkness;	51%

1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (4004-05-1) + PEG7 Bis-PFP ster → DOPE-PEG7-PFP

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃;	50%

1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (4004-05-1) + C19H16N2O6 → 3-(((2-(2-(3-benzoyl-6,7-dimethoxy-2-oxoquinoxalin-1(2H)-yl)acetamido)ethoxy)(hydroxy)phosphoryl)oxy)propane-1,2-diyl dioleate

Conditions	Yield
Stage #1: C19H16N2O6 With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide for 0.25h; Stage #2: 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine In dichloromethane; N,N-dimethyl-formamide at 20℃;	39%

1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (4004-05-1) + PEG-17 bis-NHS-ester → DOPE-PEG17-NHS

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; Inert atmosphere;	36%

1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (4004-05-1) + all-trans-retinoic-acid (302-79-4) → (Z)-(2R)-3-(((2-((2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenamido)ethoxy)(hydroxy)phosphoryl)oxy)propane-1,2-diyl dioleate (1415981-98-4)

Conditions	Yield
Stage #1: all-trans-retinoic-acid With diethylamino-sulfur trifluoride In diethyl ether at -78 - 20℃; Stage #2: 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine With sodium carbonate In chloroform at 20℃; for 24h;	28%

1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (4004-05-1) + C15H21F2NO4 → C56H97F2N2O11P

Conditions	Yield
Stage #1: C15H21F2NO4 With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide for 0.5h; Inert atmosphere; Cooling with ice; Stage #2: 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 48h; Inert atmosphere; Cooling with ice;	20.8%

1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (4004-05-1) → 1,2-distearoyl-sn-glycero-3-phosphoethanolamine (1069-79-0)

Conditions	Yield
With acetic acid; platinum Hydrogenation;

1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (4004-05-1) + estra-1,3,5(10)-triene-3,17β-diol 17β-hemisuccinate (7698-93-3, 65684-87-9, 93939-81-2) → (Z)-Octadec-9-enoic acid (R)-2-(hydroxy-{2-[3-((13S,17S)-3-hydroxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-yloxycarbonyl)-propionylamino]-ethoxy}-phosphoryloxy)-1-((Z)-octadec-9-enoyloxymethyl)-ethyl ester (139116-09-9)

Conditions	Yield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In dichloromethane; acetone for 5h;

1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (4004-05-1) + androst-4-en-3-one-17β-carboxylic acid (302-97-6) → C61H104NO10P (139116-00-0)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 6h; Ambient temperature;

Upstream product

• 71260-21-4 (Z)-Octadec-9-enoic acid 1-((Z)-octadec-9-enoyloxymethyl)-2-{(2,2,2-tribromo-ethoxy)-[2-(trityl-amino)-ethoxy]-phosphoryloxy}-ethyl ester 
• 71260-68-9 (Z)-Octadec-9-enoic acid 1-((Z)-octadec-9-enoyloxymethyl)-2-[phenylamino-(2,2,2-tribromo-ethoxy)-phosphoryloxy]-ethyl ester 
• 71260-73-6 (Z)-Octadec-9-enoic acid 2-[hydroxy-(2,2,2-tribromo-ethoxy)-phosphoryloxy]-1-((Z)-octadec-9-enoyloxymethyl)-ethyl ester 
• 2442-61-7 1,2-dioleoylglycerol 
• 69747-56-4 (Z)-Octadec-9-enoic acid 2-{hydroxy-[2-(trityl-amino)-ethoxy]-phosphoryloxy}-1-((Z)-octadec-9-enoyloxymethyl)-ethyl ester 
• 19805-13-1 L-1,2-Di-O-oleoyl-glycerin-3-phosphorsaeure-dibenzylester 
• 139115-88-1 (S)-3-(3,4-Dimethoxybenzyloxy)propane-1,2-diyl Dioleate 
• 108392-02-5 1,2-dioleoyl-sn-glycero-3-phosphate sodium salt 
• 6085-36-5 oleic anhydride 
• 4235-95-4 dioleoylphosphatidylcholine 
• 141-43-5 ethanolamine 
• 24529-88-2 1,2-dioleoyl-sn-glycerol 

Downstream Products

• 1438280-68-2 (Z)-3-((hydroxy(2-(2-((4-oxo-3-phenyl-4,5-dihydro-3H-pyrimido[5,4-b]indol-2-yl)thio)acetamido)ethoxy)phosphoryl)oxy)propane-1,2-diyl dioleate 

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