1,2-Dipalmitoyl-sn-glycero-3-phosphoethanolamine

Base Information

• Chemical Name: 1,2-Dipalmitoyl-sn-glycero-3-phosphoethanolamine
• CAS No.: 923-61-5
• Molecular Formula: C37H74NO8P
• Molecular Weight: 691.97
• Hs Code.: 29232000
• European Community (EC) Number: 213-097-1
• UNII: 4FWH120Z1Z
• DSSTox Substance ID: DTXSID90919258
• Nikkaji Number: J76.013G
• Wikipedia: Dipalmitoylphosphatidylethanolamine
• Wikidata: Q27140326
• Metabolomics Workbench ID: 15160
• Mol file: 923-61-5.mol

Synonyms:1,2-dihexadecyl-sn-glycero-3-phosphoethanolamine;1,2-dipalmitoyl-3-phosphatidylethanolamine;1,2-dipalmitoyl-3-phosphatidylethanolamine, (+-)-isomer;1,2-dipalmitoyl-3-phosphatidylethanolamine, (R)-isomer;1,2-dipalmitoyl-3-phosphatidylethanolamine, ion(1-);1,2-dipalmitoyl-rac-glycerophosphoethanolamine;1,2-dipalmitoyl-sn-glycero-3-phosphoethanolamine;DHPE;dipalmitoyl cephalin;dipalmitoyl phosphatidylethanolamine;phosphatidylethanolamine dipalmitoate

Chemical Property of 1,2-Dipalmitoyl-sn-glycero-3-phosphoethanolamine

Chemical Property:

• Melting Point: 195.0 to 199.0 °C
• Boiling Point: 723.6 °C at 760 mmHg
• PKA: 1.17±0.50(Predicted)
• Flash Point: 391.4 °C
• PSA: 144.19000
• Density: 1.01 g/cm³
• LogP: 11.19660
• Storage Temp.: −20°C
• Solubility.: Methanol (Slightly)
• XLogP3: 10.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 39
• Exact Mass: 691.51520532
• Heavy Atom Count: 47
• Complexity: 754

Purity/Quality:

98%,99%, ^*data from raw suppliers

1,2-Dipalmitoyl-sn-glycero-3-phosphorylethanolamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Lipids -> Unambiguous Lipids
• Canonical SMILES: CCCCCCCCCCCCCCCC(=O)OCC(COP(=O)(O)OCCN)OC(=O)CCCCCCCCCCCCCCC
• Isomeric SMILES: CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)OCCN)OC(=O)CCCCCCCCCCCCCCC
• Description: 1,2-Dipalmitoyl-sn-glycero-3-PE (1,2-DPPE) is a naturally occurring PE containing C16:0 fatty acids at the sn-1 and sn-2 positions. It belongs to a class of phospholipids that are the most abundant lipids in the inner leaflet of the plasma membrane. 1,2-DPPE interacts with cholesterol to form a condensed lipid monolayer with tight hydrogen bonding of the 1,2-DPPE interheadgroups, resulting in a more fluid membrane that may aid in transport and signaling across the bilayer. 1,2-Dipalmitoyl-sn-glycero-3-PE MaxSpec? standard is a quantitative grade standard of 1,2-dipalmitoyl-sn-glycero-3-PE that has been prepared specifically for mass spectrometry and related applications where quantitative reproducibility is required. The solution has been prepared gravimetrically and is supplied in a deactivated glass ampule sealed under argon. The concentration was verified by comparison to an independently prepared calibration standard. This 1,2-dipalmitoyl-sn-glycero-3-PE MaxSpec? standard is guaranteed to meet identity, purity, stability, and concentration specifications and is provided with a batch-specific certificate of analysis. Ongoing stability testing is performed to ensure the concentration remains accurate throughout the shelf life of the product. Note: The amount of solution added to the vial is in excess of the listed amount. Therefore, it is necessary to accurately measure volumes for preparation of calibration standards. Follow recommended storage and handling conditions to maintain product quality.
• Uses: 1,2-Dipalmitoyl-sn-glycero-3-phosphoethanolamine is used in model membrane . 16:0 PE has been used:for the preparation of perfluorocarbon (PFC) nanoparticlesfor lipid binding by liposome flotation assaysto characterize the metabolic fate of synaptamide in a dopaminergic cell line

Technology Process of 1,2-Dipalmitoyl-sn-glycero-3-phosphoethanolamine

There total 16 articles about 1,2-Dipalmitoyl-sn-glycero-3-phosphoethanolamine 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: 93.0%

hexadecanoic acid 3-<((2-((tert-butoxycarbonyl)amino)ethoxy)hydroxyphosphoryl)oxy>-2-(hexadecanoyloxy)propyl ester (57818-60-7) → 1,2-dipalmitoyl-3-sn-phosphatidylethanolamine (923-61-5,3026-45-7)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; for 0.75h; Ambient temperature;

DOI:10.1021/jo951350k

Reference yield: 90.0%

C55H87N2O10P → 1,2-dipalmitoyl-3-sn-phosphatidylethanolamine (923-61-5,3026-45-7)

Guidance literature:

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

Reference yield: 78.0%

(R)-3-(((2-(fluorenylmethoxycarbonylamino)ethoxy)(hydroxy)phosphoryl)oxy)propane-1,2-dipalmitate → 1,2-dipalmitoyl-3-sn-phosphatidylethanolamine (923-61-5,3026-45-7)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20 ℃; for 2h; Reagent/catalyst;

upstream raw materials:

phosphoric acid-(2-benzyloxycarbonylamino-ethyl ester)-((R)-2,3-bis-palmitoyloxy-propyl ester)-phenyl ester

1,2-dipalmitoyl-sn-glycero-3-H-phosphono-N-(tert-butoxycarbonyl)ethanolamine

N-trityl-1,2-Dipalmitoyl-sn-glycero-3-phosphoethanolamine

hexadecanoic acid 3-<((2-((tert-butoxycarbonyl)amino)ethoxy)hydroxyphosphoryl)oxy>-2-(hexadecanoyloxy)propyl ester

Downstream raw materials:

dibenzyl 1,2-dipalmitoyl-sn-glycero-3-phosphate

Hexadecanoic acid (R)-2-{[2-({(2R,3R,4R,5R,6S)-5-acetylamino-6-benzyloxy-3-hydroxy-4-[1-(4-nitro-benzyloxycarbonyl)-ethoxy]-tetrahydro-pyran-2-ylmethyl}-amino)-ethoxy]-hydroxy-phosphoryloxy}-1-hexadecanoyloxymethyl-ethyl ester

Hexadecanoic acid (R)-2-({2-[3-(4-tert-butoxycarbonylamino-phenyl)-3-methyl-ureido]-ethoxy}-hydroxy-phosphoryloxy)-1-hexadecanoyloxymethyl-ethyl ester

Refernces

• 1、 -. "A diacyl phosphatidyl ethanolamine preparation method (by machine translation)". . . Retrieved 2018/11/22.
• 2、 Roodsari, Farzaneh S.,Wu, Dongpei,Pum, Gregory S.,Hajdu, Joseph. "A new approach to the stereospecific synthesis of phospholipids. The use of L-glyceric acid for the preparation of diacylglycerols, phosphatidylcholines, and related derivatives". . p. 7727 - 7737. Retrieved 2007/10/03.