74389-69-8

Usage

Biochem/physiol Actions

C18-02:0 PC or 1-O-octadecyl-2-acetyl-sn-glycero-3-phosphocholine (C18-PAF), a platelet-activating factor (PAF) facilitates platelet aggregation and secretion. It also plays a key role in inflammation and anaphylaxis. C18-PAF exhibits neurotoxic effects by initiating caspase-independent death in PAF receptor-deficient neurons.

InChI:InChI=1/C28H58NO7P/c1-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-23-33-25-28(36-27(2)30)26-35-37(31,32)34-24-22-29(3,4)5/h28H,6-26H2,1-5H3/t28-/m1/s1

Upstream product

• 1122-58-3 dmap 
• 75213-05-7 1-O-octadecyl-2-O-acetyl-Sn glycerol 
• 6609-64-9 2-Chloro-2-oxo-1,3,2-dioxaphospholane 
• 645-84-1 choline phosphate 
• 16245-97-9 octadecyl glycidyl ether 
• 55357-38-5 choline tosylate 
• 74430-89-0 Lyso-platelet-activating factor (C₁₈) 
• 108-24-7 acetic anhydride 
• 84379-57-7 1-O-hexadecyl-2-O-benzyl-D-threitol 
• 75-50-3 trimethylamine 
• 108180-28-5 rac-2-myristoyl-1-octadecyl-3-phosphocholine 
• 10567-22-3 (R)-octadecylglycerol 
• 3386-32-1 n-octadecyl p-toluenesulfonate 
• 6076-32-0 3-O-Octadecyl-1-O-trityl-sn-glycerin 

Downstream Products

• 74430-89-0 Lyso-platelet-activating factor (C₁₈) 

Relevant academic research and scientific papers

An effective reagent to functionalize alcohols with phosphocholine

Phosphocholine is a small haptenic molecule that is both a precursor and degradation product of choline. Phosphocholine decorates a number of biologics such as lipids and oligosaccharides. In this study, an air and bench stable phosphocholine donor has been developed and evaluated with a number of alcohol acceptors. Using a one-pot, three-step sequence, (phosphitylation, oxidation, and phosphate deprotection) phosphocholine derivatives are synthesized in high yields. Of particular interest is the synthesis of miltefosine, the lone oral drug approved to treat leishmaniasis. Due to its prohibitive expense ($1500 per g), miltefosine is not accesable for the majority of the world's patients. Based on the described reaction sequence, this drug can be produced for $25 per g.

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.

Formation of a Structural Isomer of Platelet Activating Factor on the Acetylation of 1-Alkyl-sn-Glycero-3-Phosphocholines

The key stage in the synthesis of the platelet activating factor (PAT) - the acetylation of 1-alkyl-sn-glycero-3-phosphocholines (lyso-PAT) with acetic anhydride - has been studied.The formation of a structural isomer of PAT - 1-alkyl-3-acetyl-sn-glycero-3-phosphocholines - as a by-product when the reaction is carried out in the presence of bases (triethylamine, 4-dimethylaminopyridine) has been shown.Acetylation under the conditions of acid catalysis gave the isomerically pure PAT.The mechanism of the reaction leading to the formation of the PAT isomer is discussed.

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.

A Convenient Synthesis of Platelet-Activating Factors and Their Analogues from Chiral Epichlorohydrin

Two platelet activating factors (PAF) were conveniently prepared from optically active epichlorohydrin via 5 steps in 15-16percent total yield.Four analogues containing oleoyl, propyl, p-trifluoromethylphenoxy, and N,N-dimethyldithiocarbamoyl groups were also prepared.

Optically active oxiranes. Synthesis of PAF (Platelet Aggregating Factor)

A number of epoxides bearing no function in the α-position have been converted into β-hydroxy sulfonium salts.Association with an otically active acid (dibenzoyltartaric) allowed the resolution.This method has been used to prepare the optically active glycidol octadecyl ether which was converted into (-) PAF. Key words: oxiranes / resolution / PAF synthesis

Synthesis of 1-O-alkyl-2-O-acetyl-Sn-3-glyceryl-3-phosphoryl choline the enantiomer of platelet activating factor (PAF)

A novel sterospecific synthesis of biologically active ether-phospholipids (PAF) is reported, involving chemoenzymatic approach.

An efficient synthesis of Platelet-Activating Factor (PAF) via 1-o-alkyl-2-o-(3-isoxazolyl)-SN-glycero-3-phosphocholine, a new PAF agonist utilization of the 3-isoxazolyloxy group as a protected hydroxyl

Potent PAF agonists (R)-3a,b were synthesized and converted into PAF. Key steps include Mitsunobu reaction of a chiral secondary alcohol with 3-hydroxyisoxazole as the acidic component, and hydrogenolytic ring cleavage of the resulting 3-isoxazolyloxy gro

RESOLUTION OF OXIRANES. APPLICATION TO THE SYNTHESIS OF THE PLATELET AGGREGATION FACTOR

Resolution of racemic oxiranes has been achieved through their conversion into hydroxy sulfonium salts of dibenzoyltartaric acid.Thus, resolution of n-octadecyl glycidyl ether followed by reaction with phosphorylcholine and acetylation led to C18-P.A.F.