5655-17-4

Basic information

• Product Name: 1-Stearoyllysophosphatidylcholine
• Synonyms: 3,5,9-Trioxa-4-phosphaheptacosan-1-aminium, 4,7-dihydroxy-N,N,N-trimethyl-10-oxo-, hydroxide,inner salt, 4-oxide;Choline, hydroxide, dihydrogen phosphate, inner salt, 3-ester with 1-monostearin;Choline, phosphate, 3-ester with 1-monostearin (7ci);Stearoyl lysolecithin;Stearoyl lysophosphatidylcholine;1-Stearoyllysophosphatidylcholine;stearoyl alpha-lysolecithin;2-Lysophosphatidylcholine
• CAS NO: 5655-17-4
• Molecular Formula: C26H54NO7P
• Molecular Weight: 523.687
• Mol File: 5655-17-4.mol
• Article Data: 18

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: g/cm³
• CAS DataBase Reference: 1-Stearoyllysophosphatidylcholine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Stearoyllysophosphatidylcholine(5655-17-4)
• EPA Substance Registry System: 1-Stearoyllysophosphatidylcholine(5655-17-4)

Safety Data

• Safety Statements: x and POx." target="_blank">Mutation data reported. When heated to decomposition it emits toxic vapors of NOx and POx.:
• Hazardous Substances Data: 5655-17-4(Hazardous Substances Data)

Usage

Definition

ChEBI: A lysophosphatidylcholine 18:0 in which the acyl substituent is located at position 1 and is specified as stearoyl.

Upstream product

• 18678-96-1 rac.-1-Stearoyl-glycerin-benzylether-⁽²⁾-phosphorsaeure-⁽³⁾-monocholinester 
• 816-94-4 {2-[(2,3-bis-stearoyloxy-propoxy)-hydroxy-phosphoryloxy]-ethyl}-trimethyl-ammonium betaine 
• 34688-34-1 glycerolcholine phosphate 
• 17450-32-7 1-octadecanoyl-1H-imidazole 
• 18679-03-3 1-stearoyl-2-O-benzyl-rac-glycerol 
• 112-76-5 Stearoyl chloride 
• 111-63-7 vinyl stearate 
• 57-11-4 stearic acid 
• 171597-35-6 1-stearoyl-2-benzylglycerophosphocholine 
• 816-94-4 distearoylphosphatidylcholine 
• 28319-77-9 L-glycero-3-phosphorylcholine 
• 85647-89-8 (S)-1-stearoyl-2-O-benzyl-sn-glycerol 
• 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 

Downstream Products

• 6753-53-3 1-octadecanoyl-2-[cis-9,12]-octadecadienoyl-glycero-3-phosphocholine 
• 18892-74-5 1-stearoyl-2-arachidonoyl-sn-glycero-3-phosphorylcholine 
• 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

Method for synthesizing platelet activating factor (PAF) analog

The invention discloses a method for synthesizing a platelet activating factor (PAF) analog which is of a formula shown in the specification from glyceryl phosphoryl choline as a raw material according to scheme of the following three steps of reactions: 1, enabling glyceryl phosphoryl choline, a hydroxyl activator and an aliphatic hydrocarbon carbonyl compound to react to generate an intermediate1; 2, enabling the intermediate 1 to react with cyclic anhydride to generate an intermediate 2; and 3, enabling the intermediate 2 to react with nitrophenol and a condensing agent to generate a product, namely the PAF analog. In the step 1, the glyceryl phosphoryl choline is adopted as a reaction initializing raw material, and a series of PAF analogs can be derived; in the step 2, a catalyst is additionally used, so that the yield can be increased; and in the step 3, a condensing agent which is gentle in reaction condition is selected, so that reaction steps can be reduced, an acyl chloride intermediate which is good in corrosiveness and easy to dehydrate is not generated, and equipment consumption can be reduced.

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.