1069-79-0

Basic information

• Product Name: 1,2-DISTEAROYL-SN-GLYCERO-3-PHOSPHOETHANOLAMINE
• Synonyms: 1,2-DIOCTADECANOYL-SN-GLYCERO-3-PHOSPHOETHANOLAMINE;18:0 PE;DSPE;L-ALPHA-PHOSPHATIDYLETHANOLAMINE, DISTEAROYL;L-BETA,GAMMA-DISTEAROYL-ALPHA-CEPHALIN;(R)-1-[[[(2-aminoethoxy)hydroxyphosphinyl]oxy]methyl]ethane-1,2-diyl distearate;L-A-PHOSPHATIDYLETHANOLAMINE,DISTEAROYL;1,2-Dioctadecanoyl-sn-glycero-3-phosphoethanolamine, 3-sn-Phosphatidylethanolamine, 1,2-distearoyl, L-β,γ-Distearoyl-α-cephalin
• CAS NO: 1069-79-0
• Molecular Formula: C₄₁H₈₂NO₈P
• Molecular Weight: 748.07
• EINECS: 213-963-9
• Mol File: 1069-79-0.mol
• Article Data: 5

Chemical Properties

• Melting Point: 172-173℃
• Boiling Point: 760.2 °C at 760 mmHg
• Flash Point: 413.5 °C
• Appearance: /
• Density: 0.996
• Vapor Pressure: 2.68E-25mmHg at 25°C
• Refractive Index: 1.473
• Storage Temp.: −20°C
• Solubility: Chloroform (Slightly, Heated, Sonicated)
• PKA: 1.17±0.50(Predicted)
• BRN: 1730641
• CAS DataBase Reference: 1,2-DISTEAROYL-SN-GLYCERO-3-PHOSPHOETHANOLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-DISTEAROYL-SN-GLYCERO-3-PHOSPHOETHANOLAMINE(1069-79-0)
• EPA Substance Registry System: 1,2-DISTEAROYL-SN-GLYCERO-3-PHOSPHOETHANOLAMINE(1069-79-0)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• F: 10-21
• Hazardous Substances Data: 1069-79-0(Hazardous Substances Data)

Usage

Chemical Properties

White powder

Uses

1,2-Distearoyl-sn-glycero-3-phosphoethanolamine is used in the generation of micelles and liposomes.

General Description

Phosphatidylethanolamine is an aminophospholipid, which is found in eukaryotic and prokaryotic cells. It is one of the most abundant glycerophospholipids in biological membranes. Phosphatidylethanolamine is found in nervous tissue.

Biochem/physiol Actions

Phosphatidylethanolamine forms pure lipid structures. It modulates membrane fluidity in eukaryotic cells. Phosphatidylethanolamine plays an important role in autophagy, cell division and protein folding. It acts as a precursor for the synthesis of various protein modifications. Phosphatidylethanolamine functions as an intermediate for the synthesis of glycerophospholipid classes.

Purification Methods

The R-form is recrystallised from CHCl3/MeOH, and the ±-form is recrystallised from EtOH. [Bevan & Malkin J Chem Soc 2667 1951, Baer Can J Biochem Physiol 81 1758 1959, Beilstein 4 IV 1420.]

InChI:InChI=1/C41H82NO8P/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/h39H,3-38,42H2,1-2H3,(H,45,46)/t39-/m1/s1

Synthetic route

C59H95N2O10P → 1,2-distearoyl-sn-glycero-3-phosphoethanolamine (1069-79-0)

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 25℃; for 1.5h; Reagent/catalyst;	94%

Octadecanoic acid (R)-2-[(2-tert-butoxycarbonylamino-ethoxy)-hydroxy-phosphoryloxy]-1-octadecanoyloxymethyl-ethyl ester (115265-94-6) → 1,2-distearoyl-sn-glycero-3-phosphoethanolamine (1069-79-0)

Conditions	Yield
With trifluoroacetic acid In dichloromethane Ambient temperature;	93%

C44H83Cl3NO10P → 1,2-distearoyl-sn-glycero-3-phosphoethanolamine (1069-79-0)

Conditions	Yield
With acetic acid; zinc In tetrahydrofuran at 18℃; for 7h;	81.5%

C41H79N3O8P(1-)*Na(1+) → 1,2-distearoyl-sn-glycero-3-phosphoethanolamine (1069-79-0)

Conditions	Yield
With palladium on activated charcoal; hydrogen; acetic acid In methanol	80%

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;

phosphoric acid-(2-benzyloxycarbonylamino-ethyl ester)-((R)-2,3-bis-stearoyloxy-propyl ester)-phenyl ester (22430-36-0) → 1,2-distearoyl-sn-glycero-3-phosphoethanolamine (1069-79-0)

Conditions	Yield
With palladium platinum; acetic acid Hydrogenation;

1,2-distearoyl-sn-glycerol (1429-59-0, 10567-21-2) + dichloro-<-2-amino>ethyl>phosphinic acid (32159-15-2) → 1,2-distearoyl-sn-glycero-3-phosphoethanolamine (1069-79-0)

Conditions	Yield
(i) Py, CHCl3, (ii) Zn, AcOH, Et2O; Multistep reaction;

N-Trityl-O-(1,2-dioctadecanoyl-sn-glycero-3-phosphoryl)-ethanolamin (26531-41-9) → 1,2-distearoyl-sn-glycero-3-phosphoethanolamine (1069-79-0)

Conditions	Yield
With hydrogen; palladium on activated charcoal

1,2-dilinoleoyl-sn-glycero-3-phosphoethanolamine → 1,2-distearoyl-sn-glycero-3-phosphoethanolamine (1069-79-0)

Conditions	Yield
With hydrogen; platinum(IV) oxide

1,2-distearoyl-sn-glycerol (1429-59-0, 10567-21-2) → 1,2-distearoyl-sn-glycero-3-phosphoethanolamine (1069-79-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) Et3N, POCl3, 2.) Et3N / 1.) THF, 0 deg C - room temperature, 2.) THF, 0 deg C - room temperature 2: 93 percent / TFA / CH2Cl2 / Ambient temperature View Scheme
Multi-step reaction with 3 steps 1: triethylamine / tetrahydrofuran 2: sodium azide / N,N-dimethyl-formamide / 85 °C 3: palladium on activated charcoal; hydrogen; acetic acid / methanol View Scheme
Multi-step reaction with 2 steps 1.1: 1,2,3-triazole / dichloromethane / 1 h / 25 °C 1.2: 2 h / 25 °C 1.3: 0.5 h / -5 - 0 °C 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / 25 °C View Scheme

Octadecanoic acid (S)-2-(3,4-dimethoxy-benzyloxy)-1-octadecanoyloxymethyl-ethyl ester (173912-48-6) → 1,2-distearoyl-sn-glycero-3-phosphoethanolamine (1069-79-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: 90 percent / DDQ / CH2Cl2; H2O / Ambient temperature 2: 1.) Et3N, POCl3, 2.) Et3N / 1.) THF, 0 deg C - room temperature, 2.) THF, 0 deg C - room temperature 3: 93 percent / TFA / CH2Cl2 / Ambient temperature View Scheme

L-(+)-Dilinoleoyl-N-phthaloyl-α-kephalin → 1,2-distearoyl-sn-glycero-3-phosphoethanolamine (1069-79-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: aq. NaOH, N2H4*H2O 2: H2 / PtO2 View Scheme

1,2-Distearoyl-sn-glycero-3-phosphoric acid (17966-16-4) → 1,2-distearoyl-sn-glycero-3-phosphoethanolamine (1069-79-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 2,4,6-triisopropyl-benzenesulfonyl chloride, Py / CHCl3 2: H2 / Pd-C View Scheme

C14H22Cl3N2O8P → 1,2-distearoyl-sn-glycero-3-phosphoethanolamine (1069-79-0)

Conditions	Yield
Multi-step reaction with 4 steps 1: hydrogenchloride / methanol / 8 h / 18 °C 2: dmap; dicyclohexyl-carbodiimide / dichloromethane / 4.5 h / 18 °C / Cooling with ice 3: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 0.5 h / 18 °C / Cooling with ice 4: acetic acid; zinc / tetrahydrofuran / 7 h / 18 °C View Scheme

C11H18Cl3N2O8P → 1,2-distearoyl-sn-glycero-3-phosphoethanolamine (1069-79-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: dmap; dicyclohexyl-carbodiimide / dichloromethane / 4.5 h / 18 °C / Cooling with ice 2: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 0.5 h / 18 °C / Cooling with ice 3: acetic acid; zinc / tetrahydrofuran / 7 h / 18 °C View Scheme

1,2-distearoyl-sn-glycero-3-phosphoethanolamine (1069-79-0) + N-<4-((tert-butoxycarbonyl)amino)phenyl>-N-methylcarbamic chloride (123252-11-9) → Octadecanoic acid (R)-2-({2-[3-(4-tert-butoxycarbonylamino-phenyl)-3-methyl-ureido]-ethoxy}-hydroxy-phosphoryloxy)-1-octadecanoyloxymethyl-ethyl ester (173912-50-0)

Conditions	Yield
With triethylamine In tetrahydrofuran at 65℃;	91%

1,2-distearoyl-sn-glycero-3-phosphoethanolamine (1069-79-0) + trans-4-cycloocten-yl 2,5-dioxo-1-pyrrolidinyl ester carbonic acid → C50H94NO10P

Conditions	Yield
With triethylamine In methanol; chloroform for 5h; Inert atmosphere;	91%

1,2-distearoyl-sn-glycero-3-phosphoethanolamine (1069-79-0) + C15H12F5NO2S3 + triethylamine (121-44-8) → C50H93N2O9PS3*C6H15N

Conditions	Yield
Stage #1: 1,2-distearoyl-sn-glycero-3-phosphoethanolamine; triethylamine In dichloromethane at 20℃; Stage #2: C15H12F5NO2S3 In dichloromethane at 0 - 20℃;	90%

1,2-distearoyl-sn-glycero-3-phosphoethanolamine (1069-79-0) + 1 ,4-phenylenediisothiocyanate (4044-65-9) → C49H86N3O8PS2

Conditions	Yield
With triethylamine In methanol; chloroform for 5h;	90%

1,2-distearoyl-sn-glycero-3-phosphoethanolamine (1069-79-0) + (E)-2,5-dioxopyrrolidin-1-yl 1-(cyclooct-4-en-1-yloxy)-1-oxo-5,8,11,14-tetraoxa-2-azaheptadecan-17-oate → C61H115N2O15P

Conditions	Yield
With triethylamine In methanol; chloroform for 5h; Inert atmosphere;	88%

S-1-butyl-S'-(α-methyl-α'-acetic acid)trithiocarbonate (480436-46-2) + 1,2-distearoyl-sn-glycero-3-phosphoethanolamine (1069-79-0) → 1,2-distearoyl-sn-glycero-3-phosphoethanolamine

Conditions	Yield
With triethylamine In methanol; chloroform at 20℃; Inert atmosphere;	86%

1,2-distearoyl-sn-glycero-3-phosphoethanolamine (1069-79-0) + N-[5-({3-[5-(acetyl-hydroxy-amino)-pentylcarbamoyl]-propionyl}-hydroxy-amino)-pentyl]-N'-hydroxy-N'-{5-[3-(4-isothiocyanato-phenyl)-thioureido]-pentyl}-succinamide (1222468-90-7) → 3-((hydroxy(2-(3-(4-(3-(3,14,25-trihydroxy-2,10,13,21,24-pentaoxo-3,9,14,20,25-pentaazatriacontan-30-yl)thioureido)phenyl)thioureido)ethoxy)phosphoryl)oxy)propane-1,2-diyldistearate

Conditions	Yield
In chloroform; dimethyl sulfoxide at 50℃; for 72h; Inert atmosphere;	85%

1,2-distearoyl-sn-glycero-3-phosphoethanolamine (1069-79-0) + 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid mono(N-hydroxysuccinimidyl ester) (170908-81-3) → C57H108N5O15P

Conditions	Yield
With triethylamine In methanol; chloroform for 5h; Inert atmosphere;	82%

1,2-distearoyl-sn-glycero-3-phosphoethanolamine (1069-79-0) + 2,2′-(7-(2-((2,5-dioxopyrrolidin-1-yl)oxy)-2-oxoethyl)-1,4,7-triazonane-1,4-diyl)diacetic acid (1338231-09-6) → C53H101N4O13P

Conditions	Yield
With triethylamine In methanol; chloroform for 5h; Inert atmosphere;	80%

1,2-distearoyl-sn-glycero-3-phosphoethanolamine (1069-79-0) + C40H79N3O21 → C81H159N4O28P

Conditions	Yield
Stage #1: C40H79N3O21 With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 0.25h; Inert atmosphere; Stage #2: 1,2-distearoyl-sn-glycero-3-phosphoethanolamine In chloroform; N,N-dimethyl-formamide at 50℃; for 2h; Inert atmosphere;	77%

1,2-distearoyl-sn-glycero-3-phosphoethanolamine (1069-79-0) + 2-((17-azido-3,6,9,12,15-pentaoxaheptadec-1-yl)oxy)acetic acid (880129-82-8) → C55H107N4O15P (1462237-41-7)

Conditions	Yield
Stage #1: 2-((17-azido-3,6,9,12,15-pentaoxaheptadec-1-yl)oxy)acetic acid With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 0.25h; Inert atmosphere; Stage #2: 1,2-distearoyl-sn-glycero-3-phosphoethanolamine In chloroform; N,N-dimethyl-formamide at 50℃; for 1.5h; Inert atmosphere;	74%

1,2-distearoyl-sn-glycero-3-phosphoethanolamine (1069-79-0) + DBCO-NHS ester → C63H100N3O11P

Conditions	Yield
Stage #1: 1,2-distearoyl-sn-glycero-3-phosphoethanolamine With triethylamine In chloroform at 20℃; for 1h; Stage #2: DBCO-NHS ester In chloroform	72.1%

2,2-dimethyl-4-oxo-3,8,11,14,17,20,23,26,29,32,35,38,41-tridecaoxa-5-azatetratetracontan-44-oic acid (1415981-79-1) + 1,2-distearoyl-sn-glycero-3-phosphoethanolamine (1069-79-0) → (2R)-3-((((2,2-dimethyl-4,44-dioxo-3,8,11,14,17,20,23,26,29,32,35,38,41-tridecaoxa-5,45-diazaheptatetracontan-47-yl)oxy)(hydroxy)phosphoryl)oxy)propane-1,2-diyl distearate

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In methanol; chloroform; water at 25℃; for 4h; Inert atmosphere;	65%

1,2-distearoyl-sn-glycero-3-phosphoethanolamine (1069-79-0) + 2,5-dioxopyrrolidin-1-yl 1-(4-{2-azatricyclo[10.4.0.04,9]hexadeca-1(12),4(9),5,7,13,15-hexaen-10-yn-2-yl}-4-oxobutanamido)-3,6,9,12-tetraoxapentadecan-15-oate (1427004-19-0) → 3-((((23-(11,12-dehydrodibenzo[b,f]azocin-S(GH)-yl)-4,20,23-trioxo-7,10,13,16-tetraoxa-3,19-diazatricosyl)oxy)(hydroxy)phosphoryl)oxy)propane-1,2-diyldistearate

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 40℃; for 15h; Inert atmosphere;	57%

1,2-distearoyl-sn-glycero-3-phosphoethanolamine (1069-79-0) + [2-(2,5-dioxo-pyrrolidin-1-yloxycarbonylmethylsulfanyl)-ethylsulfanyl]-acetic acid 2,5-dioxo-pyrrolidin-1-yl ester (769193-58-0) → Octadecanoic acid (R)-2-[(2-{2-[2-({2-[((R)-2,3-bis-octadecanoyloxy-propoxy)-hydroxy-phosphoryloxy]-ethylcarbamoyl}-methylsulfanyl)-ethylsulfanyl]-acetylamino}-ethoxy)-hydroxy-phosphoryloxy]-1-octadecanoyloxymethyl-ethyl ester

Conditions	Yield
With triethylamine In chloroform	54%

1,2-distearoyl-sn-glycero-3-phosphoethanolamine (1069-79-0) + N-hydroxysuccinimide ester of 3-methylthiopropione acid (106520-77-8) → Octadecanoic acid (R)-2-{hydroxy-[2-(3-methylsulfanyl-propionylamino)-ethoxy]-phosphoryloxy}-1-octadecanoyloxymethyl-ethyl ester

Conditions	Yield
With triethylamine In chloroform	53%

1,2-distearoyl-sn-glycero-3-phosphoethanolamine (1069-79-0) + C43H73N3O22 → C80H150N3O27P

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In chloroform at 20℃; for 72h; Inert atmosphere;	43%

glutaric anhydride, (108-55-4) + 1,2-distearoyl-sn-glycero-3-phosphoethanolamine (1069-79-0) → 1,2-distearoyl-sn-glycero-3-phosphoethanol-N-aminoglutaric acid (1009838-54-3)

Conditions	Yield
With triethylamine In chloroform at 20℃; for 12h;	39.3%
With dmap; triethylamine In chloroform at 60℃; for 4h;

1,2-distearoyl-sn-glycero-3-phosphoethanolamine (1069-79-0) + N-succinimidyl-S-acetylthioacetate (76931-93-6) → SATA-DSPE (1040392-36-6)

Conditions	Yield
With triethylamine In chloroform at 20℃;	7.25%

1,2-distearoyl-sn-glycero-3-phosphoethanolamine (1069-79-0) + (2S,3S,4S,5R,6R)-3,4,5-Trihydroxy-6-(10-oxo-decyloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester → (2S,3S,4S,5R,6R)-6-(10-{2-[((R)-2,3-Bis-octadecanoyloxy-propoxy)-hydroxy-phosphoryloxy]-ethylamino}-decyloxy)-3,4,5-trihydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester

Conditions	Yield
With sodium cyanoborohydride In methanol; chloroform at 58℃; for 0.5h; Yield given;

Upstream product

• 4004-05-1 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine 
• 1429-59-0 1,2-distearoyl-sn-glycerol 
• 32159-15-2 dichloro-<-2-amino>ethyl>phosphinic acid 
• 17966-16-4 1,2-Distearoyl-sn-glycero-3-phosphoric acid 
• 173912-48-6 Octadecanoic acid (S)-2-(3,4-dimethoxy-benzyloxy)-1-octadecanoyloxymethyl-ethyl ester 
• 115265-94-6 Octadecanoic acid (R)-2-[(2-tert-butoxycarbonylamino-ethoxy)-hydroxy-phosphoryloxy]-1-octadecanoyloxymethyl-ethyl ester 
• 26531-41-9 N-Trityl-O-(1,2-dioctadecanoyl-sn-glycero-3-phosphoryl)-ethanolamin 
• 22430-36-0 phosphoric acid-(2-benzyloxycarbonylamino-ethyl ester)-((R)-2,3-bis-stearoyloxy-propyl ester)-phenyl ester 

Downstream Products

• 173912-50-0 Octadecanoic acid (R)-2-({2-[3-(4-tert-butoxycarbonylamino-phenyl)-3-methyl-ureido]-ethoxy}-hydroxy-phosphoryloxy)-1-octadecanoyloxymethyl-ethyl ester 

Relevant articles and documents

A new synthetic approach to phosphatidylethanolamine

A new synthetic method for phosphatidylethanolamine head group was developed via ring-opening of cyclic dioxaphospholane 2 with sodium azide and subsequent hydrogenation. The advantage of this strategy included short reaction steps, readily available materials and good yields.

Preparation method of disaturated acyl phosphatidylethanolamine

The invention discloses a preparation method of disaturated acyl phosphatidylethanolamine, relates to the field of compound preparation, and aims at solving the problems of low yield and high cost ofan existing synthesis method of disaturated acyl phosphatidylethanolamine, wherein the preparation method comprises the following steps: (1) carrying out phosphorylation reaction by using a one-pot method to generate a compound I; (2) mixing the compound I with acid, and carrying out hydrolysis reaction to generate a compound II; (3) carrying out esterification reaction on the compound II and saturated chain acid, namely myristic acid, palmitic acid and stearic acid to generate a compound III; (4) mixing the compound III with DBU, namely 1,8-diazabicyclo undec-7-ene, and carrying out a deprotection reaction to generate a compound IV; and (5) mixing the compound IV with zinc powder and acetic acid, and carrying out a deprotection reaction to generate the disaturated acyl phosphatidylethanolamine. The method is short in synthetic route, mild in reaction condition, wide in application range and high in yield.

Synthesis and properties of photoactivatable phospholipid derivatives designed to probe the membrane-associate domains of proteins

The total syntheses of photoactivatable phospholipidic probes 1 and 2 are described. These probes contain either an aryldiazonium function at their polar head (probes 1a and 1b) or an diazocyclohexadienonyl group attached to the end of one fatty acid side chain (probe 2) and have been designed to probe the lipid/water interface and the hydrophobic core of the membrane, respectively. The synthetic schemes include the possibility of incorporating a radio-labeled atom (tritium) for further labeling investigations. Both probes were stable in the dark under physiological conditions and could be efficiently photodecomposed at wavelengths above 300 nm, leading to the generation of highly reactive species, aryl cations and cyclohexadienonyl carbene, respectively. In addition, these probes displayed UV-absorption spectra which are compatible with tryptophan-mediated energy transfer photoactivation, which can lead potentially to an efficient mapping of the membrane-associate protein domains.