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

Lyso-PC (18:0), also known as 1-stearoyl-sn-glycero-3-phosphocholine, is a lysophosphocoline connceted to hydrophobic fatty acid tail (stearic acid) by a glycerol.

Uses

Different sources of media describe the Uses of 19420-57-6 differently. You can refer to the following data:
1. 18:0 Lyso PC has been used:to functionalize carbon nanotubes (CNTs) for the development of methods to attach DNA to CNTsto increase the level of lysophosphatidic acid (LPA) in mouseto induce TNF receptor associated factor 3 interacting protein 2 (TRAF3IP2) expression in endothelial cells (EC)
2. Stearoyl L-α-Lysolecithin is an bioactive lysophosphatidylcholine derived compound found to be released by bronchial epithelial cells. Stearoyl L-α-Lysolecithin have also been utilized in the development of liposomes and michelles by drug transdermal delivery devices.

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

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

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 
• 35418-59-8 1-stearoyl-2-arachidonoyl-sn-glycero-3-phosphocholine 
• 27098-24-4 trimethyl (2-{[(2R)-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]-3-(octadecanoyloxy)propylphosphonato]oxy}ethyl)azanium 
• 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 
• 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 

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.

Tin-mediated synthesis of lyso-phospholipids

1-O-Acyl-sn-glycero-3-phosphocholine and 1-O-acyl-sn-glycero-3-phosphoric acid have been prepared selectively and with high yields from the corresponding diols, glycerophosphoryl choline and glycerol-3-phosphate. Starting from the diols, the activated tin ketals were prepared in 2-propanol by reaction with dialkyltin oxide. The intermediates were acylated in the same solvent with long-chain fatty acid chlorides, giving the corresponding 1-acyl-lyso- phospholipids in high yield and with complete regioselectivity. The catalytic nature of the tin-mediated acylation and the relevance of the solvent are discussed. The Royal Society of Chemistry 2006.