4537-78-4

Basic information

• Product Name: 1,2-Distearoyl-sn-glycero-3-phosphoglycerol,sodium salt
• Synonyms: 1,2-DISTEAROYL-SN-GLYCERO-3-PHOSPHOGLYCEROL, SODIUM SALT;[1-[2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxy-3-octadecanoyloxy-propan-2-yl] octadecanoate;[1-[2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxy-3-octadecanoyloxypropan-2-yl] octadecanoate;stearic acid [1-[[glyceryloxy(hydroxy)phosphoryl]oxymethyl]-2-stearoyloxy-ethyl] ester
• CAS NO: 4537-78-4
• Molecular Formula: C₄₂H₈₃O₁₀P
• Molecular Weight: 823.04
• Mol File: 4537-78-4.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 796.4 °C at 760 mmHg
• Flash Point: 435.4 °C
• Appearance: White powder
• Density: 1.026 g/cm³
• Vapor Pressure: 2.51E-29mmHg at 25°C
• Refractive Index: 1.478
• CAS DataBase Reference: 1,2-Distearoyl-sn-glycero-3-phosphoglycerol,sodium salt(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Distearoyl-sn-glycero-3-phosphoglycerol,sodium salt(4537-78-4)
• EPA Substance Registry System: 1,2-Distearoyl-sn-glycero-3-phosphoglycerol,sodium salt(4537-78-4)

Safety Data

• Hazardous Substances Data: 4537-78-4(Hazardous Substances Data)

Usage

Uses

1,2-Distearoyl-sn-glycero-3-phosphorylglycerol is used as a component of a loposomal delivery system that coordinates the release of irinotecan and floxuridine in vivo. It is also used to encapsulate anthracyclines and deliver them to tumors.

Definition

ChEBI: A phosphatidylglycerol in which the phosphatidyl acyl groups are both stearoyl.

InChI:InChI=1/C42H83O10P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-41(45)49-37-40(38-51-53(47,48)50-36-39(44)35-43)52-42(46)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h39-40,43-44H,3-38H2,1-2H3,(H,47,48)

Synthetic route

1,2-distearoyl-sn-glycero-3-phospho-sn-1-glycerol, sodium → 1,2-distearoylphosphatidylglycerol (4537-78-4)

Conditions	Yield
With hydrogenchloride In chloroform; water; isopropyl alcohol at 20℃; for 0.0833333h;	93%

Octadecanoic acid 2-[(2,3-dihydroxy-propoxy)-phenylamino-phosphoryloxy]-1-octadecanoyloxymethyl-ethyl ester (64350-23-8) → 1,2-distearoylphosphatidylglycerol (4537-78-4)

Conditions	Yield
With pyridine; acetic acid; isopentyl nitrite

DL-α,β-distearin (51063-97-9) → 1,2-distearoylphosphatidylglycerol (4537-78-4)

Conditions	Yield
Multi-step reaction with 5 steps 1: 1-methyl-imidazole 2: Zn, TsOH, Py 3: 2,4,6-triisopropylbenzenesulfonyl chloride, Py 4: H2 / Pd-C 5: isopentyl nitrite, Py, AcOH View Scheme

Octadecanoic acid 2-(hydroxy-phenylamino-phosphoryloxy)-1-octadecanoyloxymethyl-ethyl ester → 1,2-distearoylphosphatidylglycerol (4537-78-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: 2,4,6-triisopropylbenzenesulfonyl chloride, Py 2: H2 / Pd-C 3: isopentyl nitrite, Py, AcOH View Scheme

Octadecanoic acid 1-octadecanoyloxymethyl-2-[phenylamino-(2,2,2-trichloro-ethoxy)-phosphoryloxy]-ethyl ester (64350-15-8) → 1,2-distearoylphosphatidylglycerol (4537-78-4)

Conditions	Yield
Multi-step reaction with 4 steps 1: Zn, TsOH, Py 2: 2,4,6-triisopropylbenzenesulfonyl chloride, Py 3: H2 / Pd-C 4: isopentyl nitrite, Py, AcOH View Scheme

Octadecanoic acid 2-[(2,3-bis-benzyloxy-propoxy)-phenylamino-phosphoryloxy]-1-octadecanoyloxymethyl-ethyl ester (64350-22-7) → 1,2-distearoylphosphatidylglycerol (4537-78-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: H2 / Pd-C 2: isopentyl nitrite, Py, AcOH View Scheme

1,2-distearoylphosphatidylglycerol (4537-78-4) + tetra(n-butyl)ammonium hydroxide (2052-49-5) → 1,2-distearoyl-sn-glycero-3-phospho-sn-1-glycerol, tetrabutylammonium salt

Conditions	Yield
In chloroform at 20℃; for 0.166667h; Inert atmosphere;	60%

Upstream product

• 64350-23-8 Octadecanoic acid 2-[(2,3-dihydroxy-propoxy)-phenylamino-phosphoryloxy]-1-octadecanoyloxymethyl-ethyl ester 
• 64350-22-7 Octadecanoic acid 2-[(2,3-bis-benzyloxy-propoxy)-phenylamino-phosphoryloxy]-1-octadecanoyloxymethyl-ethyl ester 
• 64350-15-8 Octadecanoic acid 1-octadecanoyloxymethyl-2-[phenylamino-(2,2,2-trichloro-ethoxy)-phosphoryloxy]-ethyl ester 
• 51063-97-9 DL-α,β-distearin 

Relevant articles and documents

Synthesis and characterization of picket porphyrin receptors that bind phosphatidylglycerol, an anionic phospholipid found in bacterial membranes

The lipid binding ability of four urea-picket porphyrins designed to bind to both the phosphate anion portion as well as the glycerol hydroxyl groups of phosphatidylglycerol (PG) has been investigated. Isothermal titration calorimetry (ITC) and 1H NMR were used to determine the receptor's stoichiometry of binding, association constants, and both the enthalpy and entropy of binding with the PG anion. Spectral evidence shows that the phosphate anion portion of PG is hydrogen bonded to the urea groups of the receptors. This binding interaction orients the PG anion in the receptor pocket such that its glycerol hydroxyl groups can align with a third urea picket, and results are furnished that suggest this multifunctional interaction does occur. The structure of the entire picket was found to influence the enthalpy and entropy of lipid binding. The synthesis of tetrabutlyammonium phosphatidylglycerol (TBAPG), and a detailed spectral characterization of its headgroup, is also presented.