74389-68-7 Usage
Description
1-O-HEXADECYL-2-ACETYL-SN-GLYCERO-3-PHOSPHOCHOLINE, also known as C16-02:0 PC or PAF (C16), is a phospholipid compound with the chemical formula C38H76NO7P. It is a platelet-activating factor (PAF) analog and has a hexadecyl chain at the sn-1 position, an acetyl group at the sn-2 position, and a phosphorylcholine group at the sn-3 position.
Uses
Used in Research Applications:
1-O-HEXADECYL-2-ACETYL-SN-GLYCERO-3-PHOSPHOCHOLINE is used as a substrate in enzymatic lipoprotein-associated phospholipase A2 (Lp-PLA2) activity assays. It helps in studying the enzyme's activity and its role in various physiological and pathological processes.
Used in Pharmaceutical Industry:
1-O-HEXADECYL-2-ACETYL-SN-GLYCERO-3-PHOSPHOCHOLINE is used to study its physicochemical properties and its interaction with peptides derived from the C-terminal domains of human apolipoprotein E. This helps in understanding the role of this compound in lipid metabolism and its potential therapeutic applications.
Used in Cell Biology Research:
1-O-HEXADECYL-2-ACETYL-SN-GLYCERO-3-PHOSPHOCHOLINE is used to study human airway smooth muscle cell line, as it acts as a platelet-activating factor (PAF) analog. This helps in understanding the role of PAF in cell signaling and its potential implications in various diseases.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 74389-68-7 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 7,4,3,8 and 9 respectively; the second part has 2 digits, 6 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 74389-68:
(7*7)+(6*4)+(5*3)+(4*8)+(3*9)+(2*6)+(1*8)=167
167 % 10 = 7
So 74389-68-7 is a valid CAS Registry Number.
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
74389-68-7Relevant 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
Chupin,Ostapenko,Klykov,Anikin,Screbrennikova
, p. 35 - 43 (1996)
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
Massing, Ulrich,Eibl, Hansjoerg
, p. 211 - 224 (2007/10/02)
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
Kumar,Bhakuni
, p. 3463 - 3466 (2007/10/02)
This paper describes an enantioselective enzymatic synthesis of biologically active platelet activating factor (PAF) starting from chloropyruvic acid.