2-(Hexadecanoyloxy)-1-[(phosphonooxy)methyl]ethyl hexadecanoate

Base Information

• Chemical Name: 2-(Hexadecanoyloxy)-1-[(phosphonooxy)methyl]ethyl hexadecanoate
• CAS No.: 7091-44-3
• Molecular Formula: C35H69 O8 P
• Molecular Weight: 648.902
• DSSTox Substance ID: DTXSID101301555
• Nikkaji Number: J76.017J
• Wikidata: Q27140395
• NCI Thesaurus Code: C68415
• Metabolomics Workbench ID: 20029
• Mol file: 7091-44-3.mol

Synonyms:1,2-dipalmitoyl-sn-glycero-3-phosphate;dipalmitoyl phosphatidic acid;dipalmitoylphosphatidic acid;dipalmitoylphosphatidic acid, (+-)-isomer;dipalmitoylphosphatidic acid, (R)-isomer;dipalmitoylphosphatidic acid, ammonium salt;dipalmitoylphosphatidic acid, calcium salt;dipalmitoylphosphatidic acid, sodium salt

Chemical Property of 2-(Hexadecanoyloxy)-1-[(phosphonooxy)methyl]ethyl hexadecanoate

Chemical Property:

• Vapor Pressure: 7.15E-22mmHg at 25°C
• Boiling Point: 706.9°C at 760 mmHg
• Flash Point: 381.3°C
• PSA: 129.17000
• Density: 1.015g/cm³
• LogP: 10.51330
• Storage Temp.: ?20°C
• XLogP3: 12.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 36
• Exact Mass: 648.47300615
• Heavy Atom Count: 44
• Complexity: 696

Purity/Quality:

97% ^*data from raw suppliers

1,2-DIPALMITOYL-SN-GLYCERO-3-PHOSPATE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCCCCCC(=O)OCC(COP(=O)(O)O)OC(=O)CCCCCCCCCCCCCCC
• Isomeric SMILES: CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)O)OC(=O)CCCCCCCCCCCCCCC
• Recent ClinicalTrials: Determining the Muscle Anabolic Properties of Phosphatidic Acid.

Technology Process of 2-(Hexadecanoyloxy)-1-[(phosphonooxy)methyl]ethyl hexadecanoate

There total 10 articles about 2-(Hexadecanoyloxy)-1-[(phosphonooxy)methyl]ethyl hexadecanoate 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: 89.68%

(R)-3-((dichlorophosphoryl)oxy)propane-1,2-dipalmitate (71321-85-2) → 1,2-dipalmitoyl-sn-glycero-3-phosphatidic acid (7091-44-3)

Guidance literature:

With water; sodium carbonate; for 12h; Reagent/catalyst;

Reference yield: 89.0%

L-dipalmitoylphosphatidylcholine (63-89-8) → 1,2-dipalmitoyl-sn-glycero-3-phosphatidic acid (7091-44-3)

Guidance literature:

With calcium chloride; In dichloromethane; tris hydrochloride; at 35 ℃; for 16h; pH=8; Inert atmosphere; Darkness;

DOI:10.1016/j.steroids.2010.08.001

Reference yield: 86.0%

C37H70Cl3O8P → 1,2-dipalmitoyl-sn-glycero-3-phosphatidic acid (7091-44-3)

Guidance literature:

With acetic acid; zinc; In tetrahydrofuran; at 20 ℃; for 3h; Solvent;

upstream raw materials:

(R)-O¹-diphenoxyphosphoryl-O²,O³-dipalmitoyl-glycerol

1,2-dipalmitoyl-sn-glycerol

1,2-di-O-hexacecanoyl-3-O-benzyl-sn-glycerol

n-hexadecanoyl chloride

Downstream raw materials:

dibenzyl 2-palmitoyl-sn-glicero-3-phosphate

1-phospho-2-palmitoyl-(R)-propane-1,2-diol dibenzyl ester

C₄₄H₇₉N₃O₁₅P₂^(2-)*2Na⁽¹⁺⁾

L-dipalmitoylphosphatidylcholine

Refernces

• 1、 -. "Preparation method of dipalmitoyl phosphatidic acid". Paragraph 0029; 0031-0035; 0045-0058. . Retrieved 2020/07/02.
• 2、 Smuga, Damian A.,Smuga, Ma?gorzata,?wizdor, Alina,Panek, Anna,Wawrzeńczyk, Czes?aw. "Synthesis of dehydroepiandrosterone analogues modified with phosphatidic acid moiety". experimental part. p. 1146 - 1152. Retrieved 2010/11/03.