Dioleoyl phosphoethanolamine supplier

Name
1,2-DIOLEOYL-SN-GLYCERO-3-PHOSPHOETHANOLAMINE
EINECS 200-663-8
CAS No. 4004-05-1
Article Data9
CAS DataBase
Density 1.008 g/cm³
Solubility
Melting Point 200°C(lit.)
Formula C₄₁H₇₈NO₈P
Boiling Point 759.2 °C at 760 mmHg
Molecular Weight 744.046
Flash Point 413 °C
Transport Information
Appearance lyophilized powder
Safety 36/37
Risk Codes 22-38-40-48/20/22
Molecular Structure
Hazard Symbols Xi
Synonyms 9-Octadecenoicacid (9Z)-, (1R)-1-[[[(2-aminoethoxy)hydroxyphosphinyl]oxy]methyl]-1,2-ethanediylester (9CI);9-Octadecenoic acid (Z)-,1-[[[(2-aminoethoxy)hydroxyphosphinyl]oxy]methyl]-1,2-ethanediyl ester, (R)-;Olein, 1,2-di-, 2-aminoethyl hydrogen phosphate, L- (8CI);Ethanol, 2-amino-,dihydrogen phosphate (ester), monoester with 1,2-diolein, L- (8CI);1,2-Dioleoyl-sn-glycero-3-phosphatidylethanolamine;1,2-Dioleoyl-sn-glycero-3-phosphoethanolamine;1,2-Dioleoyl-sn-glycero-3-phosphorylethanolamine;Coatsome MC 8181;Coatsome ME8181;Dioleoyl-L-a-phosphatidylethanolamine;Dioleoylphosphatidylethanolamine;
PSA 144.19000
LogP 12.30900

Synthetic route

: 4235-95-4
dioleoylphosphatidylcholine

: 141-43-5
ethanolamine

: 4004-05-1
1,2-dioleoyl-sn-glycero-3-phosphoethanolamine

Conditions

Conditions	Yield
With PLD transesterification;	90%

: L-1,2-Di-O-oleoyl-glycerin-3-phosphorsaeurebenzylester-<2-triphenylmethylamino-ethylester>

: 4004-05-1
1,2-dioleoyl-sn-glycero-3-phosphoethanolamine

Conditions

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

: 24529-88-2
1,2-dioleoyl-sn-glycerol

: 141-43-5
ethanolamine

: 4004-05-1
1,2-dioleoyl-sn-glycero-3-phosphoethanolamine

Conditions

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>: sodium-salt of phosphoric acid-<(R)-1,2-bis-oleoyloxy-propyl ester>-<2-phthalimido-ethyl ester>

: 4004-05-1
1,2-dioleoyl-sn-glycero-3-phosphoethanolamine

Conditions

Conditions	Yield
With hydrazine hydrate

: 6085-36-5, 55726-25-5, 24909-72-6
oleic anhydride

: 4004-05-1
1,2-dioleoyl-sn-glycero-3-phosphoethanolamine

Conditions

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

: 108392-02-5
1,2-dioleoyl-sn-glycero-3-phosphate sodium salt

: 4004-05-1
1,2-dioleoyl-sn-glycero-3-phosphoethanolamine

Conditions

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

: 139115-88-1
(S)-3-(3,4-Dimethoxybenzyloxy)propane-1,2-diyl Dioleate

: 4004-05-1
1,2-dioleoyl-sn-glycero-3-phosphoethanolamine

Conditions

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

: 19805-13-1
L-1,2-Di-O-oleoyl-glycerin-3-phosphorsaeure-dibenzylester

: 4004-05-1
1,2-dioleoyl-sn-glycero-3-phosphoethanolamine

Conditions

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

: 4004-05-1
1,2-dioleoyl-sn-glycero-3-phosphoethanolamine

Conditions

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

: 4004-05-1
1,2-dioleoyl-sn-glycero-3-phosphoethanolamine

: 80028-35-9
3-propionic acid

: C50H88N3O9P

Conditions

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%

: 4004-05-1
1,2-dioleoyl-sn-glycero-3-phosphoethanolamine

: 45315-76-2
N2-[N2,N6-bis(tert-butoxycarbonyl)-L-lysyl]-N6-(tert-butoxycarbonyl)-L-lysine

: C68H126N5O16P

Conditions

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%

: 4004-05-1
1,2-dioleoyl-sn-glycero-3-phosphoethanolamine

: 121030-88-4
N-hydroxysuccinimidyl ester 3-methyl-3-(2,4,5-trimethyl-3,6-dioxocyclo-hexa-1,4-dienyl) butanoic acid

: 1073588-75-6
C55H94NO11P

Conditions

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

: 4004-05-1
1,2-dioleoyl-sn-glycero-3-phosphoethanolamine

: 471-25-0
Propiolic acid

: 910227-37-1
1,2-dioleoyl-sn-glycero-3-phosphoethanoloamine-N-prop-2'-ynamide

Conditions

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

: 4004-05-1
1,2-dioleoyl-sn-glycero-3-phosphoethanolamine

: 59156-70-6
hexanedioic acid bis(N-hydroxysuccinimide ester)

: 930280-91-4
DOPE-Ad-ONSu

Conditions

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

: 4004-05-1
1,2-dioleoyl-sn-glycero-3-phosphoethanolamine

: 1149339-80-9
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

: 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

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

: 4004-05-1
1,2-dioleoyl-sn-glycero-3-phosphoethanolamine

: 134098-68-3
3-(2'-acetoxy-4',6'-dimethylphenyl)-3,3-dimethylpropanoic acid

: C56H96NO11P

Conditions

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%

: 4004-05-1
1,2-dioleoyl-sn-glycero-3-phosphoethanolamine

: 1062444-54-5
4-{[6-amino-2-(2-methoxyethoxy)-8-oxo-7H-purine-9(8H)-yl]methyl}benzoic acid

: (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

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;

: 4004-05-1
1,2-dioleoyl-sn-glycero-3-phosphoethanolamine

: 1173-43-9
fluoresceinyl 5-isothiocyanate

: C62H89N2O13PS

Conditions

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

: 153910-64-6
3-(2-((bis(benzyloxy)phosphoryl)oxy)-4,6-dimethylphenyl)-3-methylbutanoic acid

: 4004-05-1
1,2-dioleoyl-sn-glycero-3-phosphoethanolamine

: (2R)-3-(((2-(3-(2-((bis(benzyloxy)phosphoryl)oxy)-4,6-dimethylphenyl)-3-methylbutanamido)ethoxy)(hydroxy)phosphoryl)oxy)propane-1,2-diyl dioleate

Conditions

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%

: 4004-05-1
1,2-dioleoyl-sn-glycero-3-phosphoethanolamine

: 1073493-61-4
C16H17NO6

: 1073588-74-5
C53H90NO11P

Conditions

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

: 4004-05-1
1,2-dioleoyl-sn-glycero-3-phosphoethanolamine

: 57294-38-9
N-(tert-butoxycarbonyl)-4-aminobutanoic acid

: C50H93N2O11P

Conditions

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

: 4004-05-1
1,2-dioleoyl-sn-glycero-3-phosphoethanolamine

: 1415981-75-7
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

: 1415981-76-8
(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

Conditions

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

: 4004-05-1
1,2-dioleoyl-sn-glycero-3-phosphoethanolamine

: (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

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

: 4004-05-1
1,2-dioleoyl-sn-glycero-3-phosphoethanolamine

: 1062444-54-5
4-{[6-amino-2-(2-methoxyethoxy)-8-oxo-7H-purine-9(8H)-yl]methyl}benzoic acid

: 1346265-99-3
2-(4-((6-amino-2-(2-methoxyethoxy)-8-oxo-7H-purin-9(8H)-yl)methyl)benzamido)ethyl 2,3-bis(oleoyloxy)propyl phosphate

Conditions

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

: 4004-05-1
1,2-dioleoyl-sn-glycero-3-phosphoethanolamine

: (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

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%

: 4004-05-1
1,2-dioleoyl-sn-glycero-3-phosphoethanolamine

: 100-09-4
4-methoxybenzoic acid

: DOPE-Anisamide

Conditions

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

: 4004-05-1
1,2-dioleoyl-sn-glycero-3-phosphoethanolamine

: PEG7 Bis-PFP ster

: DOPE-PEG7-PFP

Conditions

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

: 4004-05-1
1,2-dioleoyl-sn-glycero-3-phosphoethanolamine

: 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

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%

: 4004-05-1
1,2-dioleoyl-sn-glycero-3-phosphoethanolamine

: PEG-17 bis-NHS-ester

: DOPE-PEG17-NHS

Conditions

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

: 4004-05-1
1,2-dioleoyl-sn-glycero-3-phosphoethanolamine

: 302-79-4
all-trans-retinoic-acid

: 1415981-98-4
(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

Conditions

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%

: 4004-05-1
1,2-dioleoyl-sn-glycero-3-phosphoethanolamine

: C15H21F2NO4

: C56H97F2N2O11P

Conditions

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%

: 4004-05-1
1,2-dioleoyl-sn-glycero-3-phosphoethanolamine

: 1069-79-0
1,2-distearoyl-sn-glycero-3-phosphoethanolamine

Conditions

Conditions	Yield
With acetic acid; platinum Hydrogenation;

: 4004-05-1
1,2-dioleoyl-sn-glycero-3-phosphoethanolamine

: 7698-93-3, 65684-87-9, 93939-81-2
estra-1,3,5(10)-triene-3,17β-diol 17β-hemisuccinate

: 139116-09-9
(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

Conditions

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

: 4004-05-1
1,2-dioleoyl-sn-glycero-3-phosphoethanolamine

: 302-97-6
androst-4-en-3-one-17β-carboxylic acid

: 139116-00-0
C61H104NO10P

Conditions

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

Dioleoyl phosphoethanolamine Specification

The Dioleoyl phosphoethanolamine with the CAS number 4004-05-1 is also called 9-Octadecenoic acid(9Z)-,1,1'-[(1R)-1-[[[(2-aminoethoxy)hydroxyphosphinyl]oxy]methyl]-1,2-ethanediyl]ester. The systematic name is 3-{[(2-aminoethoxy)(hydroxy)phosphoryl]oxy}propane-1,2-diyl (9Z,9'Z)bis-octadec-9-enoate. Its molecular formula is C₄₁H₇₈NO₈P. This chemical is lyophilized powder.

The properties of the chemical are: (1)ACD/LogP: 14.79; (2)# of Rule of 5 Violations: 2; (3)ACD/LogD (pH 5.5): 12.29; (4)ACD/LogD (pH 7.4): 12.2; (5)ACD/BCF (pH 5.5): 1000000; (6)ACD/BCF (pH 7.4): 1000000; (7)ACD/KOC (pH 5.5): 8376237.5; (8)ACD/KOC (pH 7.4): 6766294; (9)#H bond acceptors: 9; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 42; (12)Polar Surface Area: 110.41 Å²; (13)Index of Refraction: 1.483; (14)Molar Refractivity: 211.05 cm³; (15)Molar Volume: 737.9 cm³; (16)Polarizability: 83.66×10^-24cm³; (17)Surface Tension: 38.8 dyne/cm; (18)Enthalpy of Vaporization: 120.32 kJ/mol; (19)Vapour Pressure: 3.1×10^-25 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COP(=O)(OCCN)O)CCCCCCC\C=C/CCCCCCCC
(2)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-
(3)InChIKey: MWRBNPKJOOWZPW-CLFAGFIQBE

Product Name

1,2-DIOLEOYL-SN-GLYCERO-3-PHOSPHOETHANOLAMINE

Synthetic route

Dioleoyl phosphoethanolamine Specification

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