74389-68-7

Basic information

• Product Name: 1-O-HEXADECYL-2-ACETYL-SN-GLYCERO-3-PHOSPHOCHOLINE
• Synonyms: L-ALPHA-PHOSPHATIDYLCHOLINE, BETA-ACETYL-GAMMA-O-HEXADECYL;L-ALPHA-PHOSPHATIDYLCHOLINE, BETA-ACETYL-GAMMA-O-ALKYL;C16-02:0 PC;C16PAF;C16 ENANTIOMERIC PAF;1-O-AKYL-2-ACETYL-SN-GLYCERO-3-PHOSPHOCHOLINE;1-O-PALMITYL-2-ACETYL-SN-GLYCERO-3-PHOSPHOCHOLINE;1-O-HEXADECYL-2-O-ACETYL-SN-GLYCERO-3-PHOSPHOCHOLINE
• CAS NO: 74389-68-7
• Molecular Formula: C26H54NO7P
• Molecular Weight: 523.68
• Mol File: 74389-68-7.mol
• Article Data: 16

Chemical Properties

• Melting Point: 247 °C
• Appearance: /lyophilized powder
• Storage Temp.: −20°C
• Solubility: Soluble in H2O or ethanol
• BRN: 3574588
• CAS DataBase Reference: 1-O-HEXADECYL-2-ACETYL-SN-GLYCERO-3-PHOSPHOCHOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-O-HEXADECYL-2-ACETYL-SN-GLYCERO-3-PHOSPHOCHOLINE(74389-68-7)
• EPA Substance Registry System: 1-O-HEXADECYL-2-ACETYL-SN-GLYCERO-3-PHOSPHOCHOLINE(74389-68-7)

Safety Data

• Hazard Codes: Xn
• Statements: 22-38-40-48/20/22
• Safety Statements: 36/37-24/25-22
• RIDADR: UN 1888 6.1/PG 3
• WGK Germany: 3
• RTECS: EC6060000
• F: 10-21
• Hazardous Substances Data: 74389-68-7(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 74389-68-7 differently. You can refer to the following data:
1. PAF (C16) (cas# 74389-68-7) is a blood platelet-activating factor, used to study human airway smooth muscle cell line.
2. C16-02:0 PC or 1-O-hexadecyl-2-acetyl-sn-glycero-3-phosphocholine may be used as a substrate in enzymatic lipoprotein-associated phospholipase A2 (Lp-PLA2) activity assay. It may also be used to study its physicochemical properties and its interaction with peptides derived from the C-terminal domains of human apolipoprotein E.

Definition

ChEBI: A 2-acetyl-1-alkyl-sn-glycero-3-phosphocholine betaine which has hexadecyl as the alkyl group. PAF is a potent phospholipid activator and mediator of many leukocyte functions, including platelet aggregation, inflammation, and anaphylaxis.

General Description

C16-02:0 PC, also known as 1-O-hexadecyl-2-acetyl-sn-glycero-3-phosphocholine (C16 PAF) (acetyl PAF), is a platelet-activating factor (PAF). Acetyl PAF is present in the body and it contains ether-linked hexadecyl chain at the sn-1 position and an acetyl group at the sn-2 position.

Biological Activity

Endogenous platelet-activating factor (PAF) and ligand for PAF receptors. Produced by inflammatory cells and a potent chemoattractant for polymorphonuclear neutrophils. Induces increased vascular permeability.

Biochem/physiol Actions

Platelet-activating factor (PAF) is a pro-inflammatory agent that exhibits variety of biological and pharmacological effects. It plays a major role in initiation and progression of atherosclerosis. PAF acts as a potential biomarker for coronary artery diseases. It yields LysoPAF (1-O-alkyl-2-hydroxy-sn-glycero-3-phosphocholine) on hydrolysis by platelet-activating factor-acetylhydrolase.

InChI:InChI=1/C23H48NO6P/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-18-27-20-23(30-22(2)25)21-29-31(26)28-19-17-24/h23,26H,3-21,24H2,1-2H3/p+1

Upstream product

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Relevant articles and documents

On the synthesis of platelet-activating factor via acetylation of 1-alkyl-sn-glycero-3-phosphocholine. Formation of structural isomer of PAF in the presence of bases

It has been shown that platelet-activating factor (PAF) specimens prepared via acetylation of 1-alkyl-sn-glycero-3-phosphocholine (lyso-PAF) with acetic anhydride are heterogeneous. The contaminated compound was isolated and identified to be the structural isomer of PAF, 1-alkyl-3-acetyl-sn-glycero-2-phosphocholine (iso-PAF). It appeared, that iso-PAF is formed when performing the reaction in the presence of organic bases, but not under acid catalysis. The mechanism of iso-PAF formation is discussed.

New optically pure dimethylacetals of glyceraldehydes and their application for lipid and phospholipid synthesis

A convenient synthesis of new and enantiometrically pure 2-O-protected D-glyceraldehyde dimethylacetals as chiral C-3 building blocks for the synthesis of lipids and phospholipids is described.Benzyl- or allylethers are used as protecting groups in position 2 and 5 of D-mannitol.These intermediates are converted to 2-O-benzyl- or 2-O-alkyl-D-glyceraldehyde dimethylacetals by cleavage with periodic acid in methanol.The two dimethylacetals are useful for the synthesis of mixed chain phospholipids with natural configuration of ester-ester, ester-ether or ether-ether composition.Also, triglycerides with three different alkyl chains, ester of ether, can be prepared.As an example of the varsatility of the new intermediates, we describe the synthesis of 1-O-hexadecyl-2-O-acetyl-sn-glycero-3-phosphocho;ine, the so-called 'platelet activating factor' (PAF), via 1-O-hexadecyl-2-O-benzyl-sn-glycerol. Keywords: Synthetic phospholipids; PAF; Phospholipid analogues; Synthesis; Chiral pool; Glyceraldehyde; C-3 building blocks; Optical purity

Novel chemo-enzymatic synthesis of optically active platelet activating factor

This paper describes an enantioselective enzymatic synthesis of biologically active platelet activating factor (PAF) starting from chloropyruvic acid.