19420-56-5

Basic information

• Product Name: L-ALPHA-LYSOPHOSPHATIDYLCHOLINE, OLEOYL
• Synonyms: 1-oleoyl-sn-glycero-3-phosphocholine;L-A-lysophosphatidylcholine oleoyl;1-cis-9-octadecenoyl-sn-glycero-3-phosphocholine;1-cis-9-Octadecenoyl-sn-glycero-3-phosphocholine, 3-sn-Lysophosphatidylcholine, 1-oleoyl, L-γ-Oleoyl-α-lysolecithin, Lysolecithin, oleoyl;(7R,18Z)-4,7-Dihydroxy-N,N,N-triMethyl-10-oxo-,3,5,9-trioxa-4-phosphaheptacos-18-en-1-aMiniuM Inner Salt 4-Oxide;1-Oleoyl-2-hydroxy-sn-glycerol-3-phosphocholine;1-Oleoyl-sn-glycero-3-phosphorylcholine;1-O-Oleoyl-sn-glycero-3-phosphocholine
• CAS NO: 19420-56-5
• Molecular Formula: C₂₆H₅₂NO₇P
• Molecular Weight: 521.67
• Product Categories: Amines;Fatty Acid Derivatives & Lipids;Glycerols;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 19420-56-5.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• Storage Temp.: −20°C
• BRN: 4033747
• CAS DataBase Reference: L-ALPHA-LYSOPHOSPHATIDYLCHOLINE, OLEOYL(CAS DataBase Reference)
• NIST Chemistry Reference: L-ALPHA-LYSOPHOSPHATIDYLCHOLINE, OLEOYL(19420-56-5)
• EPA Substance Registry System: L-ALPHA-LYSOPHOSPHATIDYLCHOLINE, OLEOYL(19420-56-5)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• F: 10
• Hazardous Substances Data: 19420-56-5(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 19420-56-5 differently. You can refer to the following data:
1. 1-Oleoyl-sn-glycero-3-phosphocholine is a marker contained in biological sample for determination of obesity and screening method.
2. 1-Oleoyl-sn-glycero-3-phosphocholine may be used as a reference for the analysis of lysolecithins extracted from tissues and cell membranes.
3. 18:1 Lyso PC is suitable for use as a lysophospholipid?mediator to compare the effect of sphingosylphosphorylcholine (SPC). It has been used as a supplement in Yeast nitrogen base (YNB) medium to rescue choline auxotrophy.

General Description

18:1 Lyso PC (1-oleoyl-2-hydroxy-sn-glycero-3-phosphocholine) is an endogenous lipid. It has one hydrocarbon tail.

Biochem/physiol Actions

Lysophosphatidylcholine (LPC) participates as a key factor in the atherogenic activity of oxidized low-density lipoprotein (Ox-LDL). It is a well-known cluster of differentiation 1(CD1) ligand.

InChI:InChI=1/C26H52NO7P/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/h12-13,25,28H,5-11,14-24H2,1-4H3/b13-12-/t25-/m1/s1

Upstream product

• 112-77-6 (Z)-9-octadecenoyl chloride 
• 28319-77-9 L-glycero-3-phosphorylcholine 
• 84366-67-6 1,2?dioleoyl?sn?glycero?3?phosphocholine 
• 4235-95-4 dioleoylphosphatidylcholine 
• 525-66-6 propranolol 
• 6753-55-5 2-oleoyl-1-palmitoyl-sn-glycero-3-phosphocholine 
• 56815-99-7 1,2-dipalmitoleoyl-sn-glycero-3-phosphatidylcholine 

Downstream Products

• 423756-25-6 1-O-oleoyl-2-O-[12-[N-4-(azido-2,3,5,6-tetrafluorobenzoyl)]aminododecanoyl]-sn-glycero-3-phosphocholine 
• 112-80-1 cis-Octadecenoic acid 

Relevant articles and documents

Mechanism for remodeling of the acyl chain composition of cardiolipin catalyzed by Saccharomyces cerevisiae tafazzin

Remodeling of the acyl chains of cardiolipin (CL) is responsible for final molecular composition of mature CL after de novo CL synthesis in mitochondria. Yeast Saccharomyces cerevisiae undergoes tafazzin-mediated CL remodeling, in which tafazzin serves as a transacylase from phospholipids to monolyso-CL (MLCL). In light of the diversity of the acyl compositions of mature CL between different organisms, the mechanism underlying tafazzin-mediated transacylation remains to be elucidated. We investigated the mechanism responsible for transacylation using purified S. cerevisiae tafazzin with liposomes composed of various sets of acyl donors and acceptors. The results revealed that tafazzin efficiently catalyzes transacylation in liposomal membranes with highly ordered lipid bilayer structure. Tafazzin elicited unique acyl chain specificity against phosphatidylcholine (PC) as follows: linoleoyl (18:2) > oleoyl (18:1) = palmitoleoyl (16:1) ? palmitoyl (16:0). In these reactions, tafazzin selectively removed the sn-2 acyl chain of PC and transferred it into the sn-1 and sn-2 positions of MLCL isomers at equivalent rates. We demonstrated for the first time that MLCL and dilyso-CL have inherent abilities to function as an acyl donor to monolyso-PC and acyl acceptor from PC, respectively. Furthermore, a Barth syndrome-associated tafazzin mutant (H77Q) was shown to completely lack the catalytic activity in our assay. It is difficult to reconcile the present results with the so-called thermodynamic remodeling hypothesis, which premises that tafazzin reacylates MLCL by unsaturated acyl chains only in disordered non-bilayer lipid domain. The acyl specificity of tafazzin may be one of the factors that determine the acyl composition of mature CL in S. cerevisiae mitochondria.

Lytic reactions of drugs with lipid membranes

Propranolol is shown to undergo lipidation reactions in three types of lipid membrane: (1) synthetic single-component glycerophospholipid liposomes; (2) liposomes formed from complex lipid mixtures extracted from E. coli or liver cells; and (3) in cellulo in Hep G2 cells. Fourteen different lipidated propranolol homologues were identified in extracts from Hep G2 cells cultured in a medium supplemented with propranolol. This isolation of lipidated drug molecules from liver cells demonstrates a new drug reactivity in living systems. Acyl transfer from lipids to the alcoholic group of propranolol was favoured over transfer to the secondary amine. Migration of acyl groups from the alcohol to the amine was diminished. Other drugs that were examined did not form detectable levels of lipidation products, but many of these drugs did affect the lysolipid levels in model membranes. The propensity for a compound to induce lysolipid formation in a model system was found to be a predictor for phospholipidosis activity in cellulo.

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.