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

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

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.

Production method for lysophosphatidyl choline

The invention provides a production method for lysophosphatidyl choline. By taking glycerol phosphocholine as a raw material, the lysophosphatidyl choline containing single ester group can be obtained by tin complexing and o-acylation; therefore, the production cost is low. The production method for the lysophosphatidyl choline, provided by the invention, has the advantages of short process route, simple treatment method and easy product purification.

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.

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.

γ-Ray irradiation of liposomes of polymerizable phospholipids containing octadeca-2,4-dienoyl groups and characterization of the irradiated liposomes

The synthesis of a variety of polymerizable phospholipids containing the octadeca-2,4-dienoyl moiety on 2-acyl chains and the characteristics of liposomes containing those phospholipids of the γ-irradiation are described. We synthesized three different polymerizable phosphocholines that have different 1-acyl chain lengths with the octadeca-2,4-dienoyl moiety on the 2- acyl chain: myristoyl (MODPC), palmitoyl (PODPC) and stearoyl (SODPC). The liposomes were prepared by extrusion through polycarbonate filters with a pore size of 0.2 μm, and were polymerized by γ-irradiation with various dose rates. The polymerization rate increased in the order SODPC>MODPC>PODPC. The mechanism of the polymerization of SODPC was the same as that of 1,2-bis- [(E,E)-octadeca-2,4-dienoyl]-sn-glycero-3-phosphocholine (DODPC), but differed from that of MODPC and PODPC. Freeze-thaw testing was used to evaluate the stability of the polymerizable liposomes. The MODPC liposome was more stable than other monofunctional liposomes. For similar irradiation, the polymerization behavior of the liposomes was significantly affected by the 1- acyl length.

Effects of molecular structures on the olfactory responses of phospholipid membranes to four alcohols

In order to understand the relationship between phospholipid molecular structures and their olfactory responses to odorants, we designed and synthesized four phosphatidylcholine analogues with different long hydrocarbon (CH) chains and selected three natural phospholipids with different head-groups. By using interdigital electrodes (IEs) as olfactory sensors (OSs), we measured the responses of the IEs coated with these seven different lipid membranes to four alcohol vapors in a gas flow system. The IEs voltage changes were recorded and the voltage-relative saturate vapor pressure (V-P/P°) curves were also plotted. It was found that with a methyl (-CH3) placed at the C-8 position in the 18-carbon chain, the olfactory responses could be improved about ten times and with conjugated double bonds (C=C) in the long chains, the sensitivity could be increased by 3~4 orders of magnitude. As to head-groups, choline is preferred over ethanolamine and serine in phospholipid structures in terms of high olfactory sensitivity. These results are expected to be useful in further designing and manufacturing lipid-mimicking OSs. Copyright (C) 1998 Elsevier Science Ireland Ltd.

The stereospecific synthesis of mixed-acid phospholipids with polyunsaturated fatty acid from D-mannitol

The polyunsaturated mixed-acid phosphatidylcholine, 1-palimoyl-2-linolenoyl-sn-glycerophosphocholine 1a and 1-stearoyl-2-linolenoyl-sn-glycerophosph 1b prepared from D-mannitol as an optically active starting material is described.

Asymmetric synthesis of diacylglycerophosphocholine hydroperoxide VIa, lipoxygenase-catalyzed hydroperoxidation of linoleic acid and lipase-catalyzed enantioselective stearoylation of 2-O-benzoyl-1,3-propanediol

Phosphatidylcholine hydroperoxide (11) bearing (S)-13-hydroperoxy-9Z,11E-octadecadienoic acid has been synthesized for the first time using lipoxygenase and lipase in addition to conventional chemical methods.As an extension of the study, lipase-catalyzed