19420-57-6

Basic information

• Product Name: L-ALPHA-LYSOPHOSPHATIDYLCHOLINE, STEAROYL
• Synonyms: L-A-lysophosphatidylcholine,*stearoyl (C18:0);1-Stearoyl-L-alpha-lysolecithine;Stearoyl;l-α-lysophosphatidylcholine, stearoyl;L-α-Lysophosphatidylcholine, stearoyl, Lysolecithin, stearoyl;Stearoyl Lyso-phosphocholine;1-Stearoyl-2-hydroxy-sn-glycero-3-phosphocholine L-1518;Stearoyl L-α-Lysolecithin
• CAS NO: 19420-57-6
• Molecular Formula: C₂₆H₅₄NO₇P
• Molecular Weight: 523.68
• Mol File: 19420-57-6.mol
• Article Data: 12

Chemical Properties

• Melting Point: 100-200 °C
• Appearance: white/powder
• Storage Temp.: −20°C
• Solubility: Methanol (Slightly, Heated, Sonicated), Water (Slightly, Heated)
• Stability: Hygroscopic, Moisture Sensitive
• CAS DataBase Reference: L-ALPHA-LYSOPHOSPHATIDYLCHOLINE, STEAROYL(CAS DataBase Reference)
• NIST Chemistry Reference: L-ALPHA-LYSOPHOSPHATIDYLCHOLINE, STEAROYL(19420-57-6)
• EPA Substance Registry System: L-ALPHA-LYSOPHOSPHATIDYLCHOLINE, STEAROYL(19420-57-6)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 19420-57-6(Hazardous Substances Data)

Usage

Description

L-ALPHA-LYSOPHOSPHATIDYLCHOLINE, STEAROYL, also known as 1-stearoyl-sn-glycero-3-phosphocholine or Stearoyl L-α-Lysolecithin, is a bioactive lysophosphatidylcholine derived compound that is connected to a hydrophobic fatty acid tail (stearic acid) by a glycerol. It is found to be released by bronchial epithelial cells and has various applications in different industries.
Used in Biomedical Applications:
L-ALPHA-LYSOPHOSPHATIDYLCHOLINE, STEAROYL is used as a functionalizing agent for carbon nanotubes (CNTs) to develop methods to attach DNA to CNTs. This helps in the advancement of nanotechnology-based drug delivery systems and diagnostic tools.
Used in Pharmaceutical Industry:
L-ALPHA-LYSOPHOSPHATIDYLCHOLINE, STEAROYL is used to increase the level of lysophosphatidic acid (LPA) in mouse models. This aids in studying the effects of LPA on various biological processes and its potential therapeutic applications.
Used in Immunology Research:
L-ALPHA-LYSOPHOSPHATIDYLCHOLINE, STEAROYL is used to induce TNF receptor associated factor 3 interacting protein 2 (TRAF3IP2) expression in endothelial cells (EC). This helps in understanding the role of TRAF3IP2 in immune responses and its potential as a therapeutic target.
Used in Drug Delivery Systems:
L-ALPHA-LYSOPHOSPHATIDYLCHOLINE, STEAROYL is used in the development of liposomes and micelles by drug transdermal delivery devices. Its amphiphilic nature allows it to form stable structures that can encapsulate and deliver drugs across the skin, improving the bioavailability and efficacy of various pharmaceutical agents.

Biochem/physiol Actions

1-Stearoyl-sn-glycero-3-phosphocholine (LPC, Lyso-PC) is used in the development of drug transdermal delivery devices such as liposomes and micelles.

InChI:InChI=1/C26H55NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-26(29)32-23-25(28)24-34-35(30,31)33-22-21-27(2,3)4/h25,28H,5-24H2,1-4H3,(H,30,31)

Upstream product

• 171597-35-6 1-stearoyl-2-benzylglycerophosphocholine 
• 816-94-4 distearoylphosphatidylcholine 
• 28319-77-9 L-glycero-3-phosphorylcholine 
• 112-76-5 Stearoyl chloride 
• 85647-89-8 (S)-1-stearoyl-2-O-benzyl-sn-glycerol 
• 57-11-4 stearic acid 
• 171505-41-2 Octadecanoic acid (R)-2-benzyloxy-3-oxo-propyl ester 
• 171505-42-3 Octadecanoic acid (R)-2-benzyloxy-3-[(2-chloro-ethoxy)-hydroxy-phosphoryloxy]-propyl ester 
• 111-63-7 vinyl stearate 
• 55357-38-5 choline tosylate 
• 818-08-6 di(n-butyl)tin oxide 
• 112-67-4 n-hexadecanoyl chloride 
• 66701-63-1 1,2-dipalmitoyl-sn-3-glycero-phosphatidylcholine 

Downstream Products

• 264874-86-4 1-octadecanoyl-2-[5-(tert-butyldiphenylsilyloxy)hept-6-en-1-oyl]-sn-glycero-3-phosphocholine 
• 264874-81-9 1-octadecanoyl-2-[7-(tert-butyldiphenylsilyloxy)hept-5(Z)-enoyl]-sn-glycero-3-phosphocholine 
• 143447-37-4 (9Z,11E)-(S)-13-Hydroperoxy-octadeca-9,11-dienoic acid (R)-2-[((S)-2,3-dihydroxy-propoxy)-hydroxy-phosphoryloxy]-1-octadecanoyloxymethyl-ethyl ester; compound with ammonia 
• 143447-36-3 (9Z,11E)-(S)-13-(1-Methoxy-1-methyl-ethylperoxy)-octadeca-9,11-dienoic acid (R)-2-[((S)-2,3-dihydroxy-propoxy)-hydroxy-phosphoryloxy]-1-octadecanoyloxymethyl-ethyl ester; compound with ammonia 
• 27098-24-4 trimethyl (2-{[(2R)-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]-3-(octadecanoyloxy)propylphosphonato]oxy}ethyl)azanium 
• 35418-59-8 1-stearoyl-2-arachidonoyl-sn-glycero-3-phosphocholine 

Relevant articles and documents

Light-Controlled Lipid Interaction and Membrane Organization in Photolipid Bilayer Vesicles

Controlling lateral interactions between lipid molecules in a bilayer membrane to guide membrane organization and domain formation is a key factor for studying and emulating membrane functionality in synthetic biological systems. Here, we demonstrate an approach to reversibly control lipid organization, domain formation, and membrane stiffness of phospholipid bilayer membranes using the photoswitchable phospholipid azo-PC. azo-PC contains an azobenzene group in the sn2 acyl chain that undergoes reversible photoisomerization on illumination with UV-A and visible light. We demonstrate that the concentration of the photolipid molecules and also the assembly and disassembly of photolipids into lipid domains can be monitored by UV-vis spectroscopy because of a blue shift induced by photolipid aggregation.

Phosphatidylcholine with cis-9,trans-11 and trans-10,cis-12 Conjugated Linoleic Acid Isomers: Synthesis and Cytotoxic Studies

Novel phosphatidylcholines and lysophosphatidylcholines with cis-9,trans-11 and trans-10,cis-12 conjugated linoleic acid (CLA) were synthesized in high yields (75-99%). The in vitro cytotoxic activities of these compounds against three human cancer cell lines (HL-60, MCF-7, and HT-29) were evaluated. The results revealed that there are differences in the activity between phosphatidylcholine with cis-9,trans-11 and trans-10,cis-12 CLA acyl groups. 1,2-Di(9Z,11E)-octadecadienoyl-sn-glycero-3-phosphocholine was the most potent cytotoxic agent among all tested CLA derivatives and its IC50 (concentration of a compound that inhibits the proliferation of 50% of the cancer cell population) was 29.4M against HL-60. Moreover, phosphatidylcholines with CLA acyls exhibited much lower cytotoxicity against non-cancer cells (Balb/3T3) than free CLA isomers.

Process for preparing lysophoshatidylcholine

What is described is a process for preparing lysophosphatidylcholine by selective monoacylation of glycerophosphorylcholine (I), in the presence of an acylating agent and of dialkyltin derivatives, according to the following diagram: the process being particularly simple and having high overall yields.