82755-92-8

Basic information

• Product Name: 2-(octadecanoylamino)ethyl 2-(trimethylammonio)ethyl phosphate
• Synonyms: ethanaminium, 2-[[hydroxy[2-[(1-oxooctadecyl)amino]ethoxy]phosphinyl]oxy]-N,N,N-trimethyl-, inner salt
• CAS NO: 82755-92-8
• Molecular Formula: C₂₅H₅₃N₂O₅P
• Molecular Weight: 492.6725
• Mol File: 82755-92-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 2-(octadecanoylamino)ethyl 2-(trimethylammonio)ethyl phosphate(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(octadecanoylamino)ethyl 2-(trimethylammonio)ethyl phosphate(82755-92-8)
• EPA Substance Registry System: 2-(octadecanoylamino)ethyl 2-(trimethylammonio)ethyl phosphate(82755-92-8)

Safety Data

• Hazardous Substances Data: 82755-92-8(Hazardous Substances Data)

Usage

Molecular structure

The compound has a long chain of 18 carbon atoms attached to an aminoethyl group, and a second aminoethyl group bearing a trimethylammonio moiety.

Classification

It is a phospholipid derivative, commonly referred to as a phosphatidylcholine.

Biological role

It is an important component of cell membranes and plays a role in cell signaling and membrane integrity.

Industrial use

Phosphatidylcholine is used in pharmaceuticals and cosmetics due to its emulsifying and moisturizing properties. It can also be used as a surfactant in various industries.

Upstream product

• 112-76-5 Stearoyl chloride 
• 111-57-9 N-stearoylethanolamine 
• 131933-62-5 2-octadecanamidoethyl 2'-bromoethyl phosphate 
• 75-50-3 trimethylamine 

Relevant articles and documents

In Vitro Evaluation of Phosphocholine and Quaternary Ammonium Containing Lipids as Novel Anti-HIV Agents

A series of synthetic lipids containing a two- or three-carbon backbone substituted with a thio, oxy, or amidoalkyl functionality and either a phosphocholine or quaternary ammonium moiety was evaluated as potential anti-HIV-1 agents.Several analogues were identified as possessing activity with the most promising compound being rac-3-octadecanamido-2-ethoxypropylphosphocholine (8).Compound 8 exhibited an IC50 for the inhibition of plaque formation of 0.16 μM wich was 84-fold lower than the IC50 value determined for CEM-SS cell growth inhibition.Initial mechanistic studies have indicated that these compounds, unlike AZT, are not reverse transcriptase (RT) inhibitors, but instead appear to inhibit a late step in HIV replication involving virus assembly and infectious virus production.Since these lipids are acting via a different mechanism, they represent an alternative approach to the chemotherapeutic treatment of AIDS as well as candidates for combination therapy with AZT.