Dioleoylphosphatidylglycerol

Base Information

• Chemical Name: Dioleoylphosphatidylglycerol
• CAS No.: 62700-69-0
• Molecular Formula: C42H79O10P
• Molecular Weight: 775.0444
• DSSTox Substance ID: DTXSID201273171
• Nikkaji Number: J2.615.710B
• Mol file: 62700-69-0.mol

Synonyms:1,2-dioleoyl-sn-glycero-3-phospho(1-rac-glycerol);1,2-dioleoyl-sn-glycero-3-phosphoglycerol;1,2-dioleoyl-sn-glycero-3-phosphoglycerol, (R-(R*,S*))-(Z)-isomer;1,2-dioleoyl-sn-glycero-3-phosphoglycerol, (Z)-isomer;1,2-dioleoylphosphatidylglycerol;di-C18-1(C)-PG;DOPG

Chemical Property of Dioleoylphosphatidylglycerol

Chemical Property:

• Boiling Point: 795.8 °C at 760 mmHg
• Flash Point: 435.1 °C
• PSA: 158.63000
• Density: 1.038 g/cm³
• LogP: 11.00320
• XLogP3: 12.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 42
• Exact Mass: 774.54108571
• Heavy Atom Count: 53
• Complexity: 941

Purity/Quality:

99.0% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCC=CCCCCCCCC(=O)OCC(COP(=O)(O)OCC(CO)O)OC(=O)CCCCCCCC=CCCCCCCCC
• Isomeric SMILES: CCCCCCCC/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(O)OCC(CO)O)OC(=O)CCCCCCC/C=C\CCCCCCCC

Technology Process of Dioleoylphosphatidylglycerol

There total 7 articles about Dioleoylphosphatidylglycerol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 56.0%

(2R)-3-((((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propoxy)(2-cyanoethoxy)phosphoryl)oxy)propane-1,2-diyl dioleate → L-α-dioleoylphosphatidylglycerol (62700-69-0)

Guidance literature:

With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; at 23 ℃; for 24h; Schlenk technique; Inert atmosphere;

DOI:10.1016/j.chemphyslip.2020.104933

Reference yield:

dioleoylphosphatidylcholine (4235-95-4) + glycerol (56-81-5,25618-55-7,64333-26-2,8013-25-0) → 1,2-dioleoyl-sn-glycero-3-[phospho-rac-(1-glycerol)] (62700-69-0)

Guidance literature:

With CaCl₂ buffer; sodium acetate; acetic acid; In chloroform; at 30 ℃; for 4h; phospholipase D from Streptomyces sp., pH 6.5;

DOI:10.1021/ja00076a004

Reference yield:

(S)-3-((4-methoxybenzyl)oxy)propane-1,2-diyl dioleate (143997-01-7) → L-α-dioleoylphosphatidylglycerol (62700-69-0)

Guidance literature:

Multi-step reaction with 4 steps

1: aluminium; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 24 h / 24 °C

2: 1H-tetrazole / dichloromethane / 16 h / 24 °C / Schlenk technique; Inert atmosphere

3: tert.-butylhydroperoxide / dichloromethane; water / 24 °C / Schlenk technique; Inert atmosphere

4: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 24 h / 23 °C / Schlenk technique; Inert atmosphere

With 1H-tetrazole; tert.-butylhydroperoxide; tetrabutyl ammonium fluoride; acetic acid; aluminium; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; water;

DOI:10.1016/j.chemphyslip.2020.104933

upstream raw materials:

1,2-dioleoyl-sn-glycerol

dioleoylphosphatidylcholine

glycerol

(S)-3-((4-methoxybenzyl)oxy)propane-1,2-diyl dioleate

Refernces

• 1、 Storch, Judith,Struzik, Zachary J.,Thompson, David H.,Weerts, Ashley N.. "Stereospecific synthesis of phosphatidylglycerol using a cyanoethyl phosphoramidite precursor". . . Retrieved 2020/07/03.