1-O-octadecyl-2-hydroxy-sn-glycero-3-phosphocholine - ≥99% , CAS No.74430-89-0

CAS: 74430-89-0 Cat. No.: O130791 Molecular Weight: 509.7

GRADE & PURITY ≥99%

Synonyms

1-Octadecyl-sn-glycero-3-phosphocholine | MFCD00065889 | XKBJVQHMEXMFDZ-AREMUKBSSA-N | 1-o-octadecyl-2-hydroxy-sn-glycero-3-phosphocholine | [(2R)-2-hydroxy-3-octadecoxypropyl] 2-(trimethylazaniumyl)ethyl phosphate | (R)-2-Hydroxy-3-(octadecyloxy)propyl (

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

General description：

C18-lysoPAF, also known as 1-O-octadecyl-2-hydroxy-sn-glycero-3-phosphocholine, is a synthetic lyso-platelet activating factor (PAF). It is a precursor and metabolite of 1-O-octadecyl-2-acetyl-sn-glycero-3-phosphocholine (C18:0 PAF). Lyso-platelet activating factor (PAF) is synthesized from PAF acetylhydrolases by the degradation of PAF. Additionally, it is also synthesized in the remodeling pathway from 1-O-alkyl-2-arachidonoyl-sn-glycero-3-phosphocholine (1-alkyl-phosphatidylcholine) by the enzyme phospholipase.

Application：

C18-lysoPAF (1-O-octadecyl-2-hydroxy-sn-glycero-3-phosphocholine) has been used to study its effect on human eosinophil degranulation.

Specifications

Synonyms

1-Octadecyl-sn-glycero-3-phosphocholine | MFCD00065889 | XKBJVQHMEXMFDZ-AREMUKBSSA-N | 1-o-octadecyl-2-hydroxy-sn-glycero-3-phosphocholine | [(2R)-2-hydroxy-3-octadecoxypropyl] 2-(trimethylazaniumyl)ethyl phosphate | (R)-2-Hydroxy-3-(octadecyloxy)propyl (

Specifications & Purity

≥99%

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥99%

Names and Identifiers

• Canonical Smiles: CCCCCCCCCCCCCCCCCCOCC(COP(=O)([O-])OCC[N+](C)(C)C)O
• IUPAC Name: [(2R)-2-hydroxy-3-octadecoxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
• InChIKey: XKBJVQHMEXMFDZ-AREMUKBSSA-N
• INCHI: 1S/C26H56NO6P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-22-31-24-26(28)25-33-34(29,30)32-23-21-27(2,3)4/h26,28H,5-25H2,1-4H3/t26-/m1/s1
• Isomeric SMILES: CCCCCCCCCCCCCCCCCCOC[C@H](COP(=O)([O-])OCC[N+](C)(C)C)O
• Molecular Weight: 509.7
• Reaxy-Rn: 4721672
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=4721672&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Glycerophospholipids
      • Subclass Glycerophosphocholines

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Glycerophospholipids
• Subclass: Glycerophosphocholines
• Intermediate Tree Nodes: Not available
• Direct Parent: Monoalkylglycerophosphocholines
• Alternative Parents: Phosphocholines Glycerol ethers Dialkyl phosphates Tetraalkylammonium salts Secondary alcohols Dialkyl ethers Organopnictogen compounds Organic salts Organic oxides Hydrocarbon derivatives Amines
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Monoalkylglycerophosphocholine - Phosphocholine - Glycerol ether - Dialkyl phosphate - Organic phosphoric acid derivative - Phosphoric acid ester - Alkyl phosphate - Quaternary ammonium salt - Tetraalkylammonium salt - Secondary alcohol - Ether - Dialkyl ether - Hydrocarbon derivative - Alcohol - Organic oxide - Organopnictogen compound - Organic oxygen compound - Organooxygen compound - Organonitrogen compound - Organic nitrogen compound - Amine - Organic salt - Aliphatic acyclic compound
• Description: This compound belongs to the class of organic compounds known as monoalkylglycerophosphocholines. These are compounds containing glycerophosphocholine moiety attached to an fatty acyl chain through an ether bond.
• External Descriptors: Monoalkylglycerophosphocholines

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Mechanisms of Action

Chemical and Physical Properties

• Molecular Weight: 509.700 g/mol
• XLogP3: 7.000
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 26
• Exact Mass: 509.385 Da
• Monoisotopic Mass: 509.385 Da
• Topological Polar Surface Area: 88.100 Ų
• Heavy Atom Count: 34
• Formal Charge: 0
• Complexity: 478.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 1
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1