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Cas Database

Name	Dioleoyl phosphoethanolamine	EINECS	200-663-8
CAS No.	4004-05-1	Density	1.008 g/cm³
PSA	144.19000	LogP	12.30900
Solubility	N/A	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	N/A	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;	Article Data	9

Dioleoyl phosphoethanolamine 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%

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

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