1-Palmitoyl-2-acetyl-sn-glycero-3-phosphocholine

Base Information

• Chemical Name: 1-Palmitoyl-2-acetyl-sn-glycero-3-phosphocholine
• CAS No.: 79512-78-0
• Molecular Formula: C₂₆H₅₂NO₈P
• Molecular Weight: 537.675
• ChEMBL ID: CHEMBL1335151
• DSSTox Substance ID: DTXSID701105288
• Metabolomics Workbench ID: 13407
• Wikidata: Q27145169
• Mol file: 79512-78-0.mol

Synonyms:1-palmitoyl-2-acetyl-glycerophosphocholine;1-palmitoyl-2-acetyl-GPC;1-palmitoyl-2-acetyl-sn-glycero-3-phosphocholine;1-palmitoyl-2-acetyl-sn-glycero-3-phosphocholine, (R)-isomer;PA-GPC;PAGPC

Chemical Property of 1-Palmitoyl-2-acetyl-sn-glycero-3-phosphocholine

Chemical Property:

• PSA: 121.00000
• LogP: 6.22060
• XLogP3: 6.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 26
• Exact Mass: 537.34305461
• Heavy Atom Count: 36
• Complexity: 615

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCCCCCC(=O)OCC(COP(=O)([O-])OCC[N+](C)(C)C)OC(=O)C
• Isomeric SMILES: CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)([O-])OCC[N+](C)(C)C)OC(=O)C
• Uses: 1-Palmitoyl-2-acetyl-sn-glycero-3-phosphorylcholine is used in the mRNA combination therapy for treatment of cancer.

Technology Process of 1-Palmitoyl-2-acetyl-sn-glycero-3-phosphocholine

There total 5 articles about 1-Palmitoyl-2-acetyl-sn-glycero-3-phosphocholine 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: 65.0%

1-palmitoyl-sn-glycero-3-phosphocholine (17364-16-8,17364-17-9,17364-18-0,14863-27-5) + acetic anhydride (108-24-7) → 1-palmitoyl-2-O-acetyl-sn-glycero-3-phosphocholine (79512-78-0,115154-33-1,84062-61-3)

Guidance literature:

With dmap; In dichloromethane; at 20 ℃; for 20h;

DOI:10.1007/s11746-008-1280-4

Reference yield:

1-0-triphenylmethyl-2-acetyl-sn-glycero-3-phosphocholine + palmitic anhydride (623-65-4) → 1-palmitoyl-2-O-acetyl-sn-glycero-3-phosphocholine (79512-78-0,115154-33-1,84062-61-3)

Guidance literature:

Reference yield:

L-glycero-3-phosphorylcholine (28319-77-9,563-24-6) → 1-palmitoyl-2-O-acetyl-sn-glycero-3-phosphocholine (79512-78-0,115154-33-1,84062-61-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: dibutyltin oxide / propan-2-ol / 1 h / Heating

1.2: 80 percent / TEA / propan-2-ol / 0.25 h / 25 °C

2.1: 4-dimethylaminopyridine / CH₂Cl₂ / 20 h / 20 °C

With dmap; di(n-butyl)tin oxide; In dichloromethane; isopropyl alcohol;

DOI:10.1016/j.chemphyslip.2007.03.008

upstream raw materials:

1-palmitoyl-sn-glycero-3-phosphocholine

acetic anhydride

L-glycero-3-phosphorylcholine

n-hexadecanoyl chloride