52691-62-0

Basic information

• Product Name: 1-O-HEXADECYL-SN-GLYCERO-3-PHOSPHOCHOLINE
• Synonyms: 1-O-hexadecyl-2-lyso-glycero-3-phosphorylcholine;GAMMA-O-HEXADECYL L-A-LYSOPHOSPHATIDYLCHOLINE;1-Hexadecyl-sn-glycero-3-phosphocholine, 3-sn-Lysophosphatidylcholine, 1-hexadecyl, Lyso-PAF-C16, Lyso-platelet activating factor;1-O-Alkyl-sn-glycero-3-phosphocholine, Lyso-platelet activating factor;γ-O-Alkyl-L-α-lysophosphatidylcholine from bovine heart;Lyso-PAF (C16),98%;1-hexadecyl;3-sn-Lysophosphatidylcholine, 1-hexadecyl
• CAS NO: 52691-62-0
• Molecular Formula: C24H52NO6P
• Molecular Weight: 481.65
• Mol File: 52691-62-0.mol
• Article Data: 13

Chemical Properties

• Appearance: white solid
• Storage Temp.: −20°C
• CAS DataBase Reference: 1-O-HEXADECYL-SN-GLYCERO-3-PHOSPHOCHOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-O-HEXADECYL-SN-GLYCERO-3-PHOSPHOCHOLINE(52691-62-0)
• EPA Substance Registry System: 1-O-HEXADECYL-SN-GLYCERO-3-PHOSPHOCHOLINE(52691-62-0)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• F: 10-21
• Hazardous Substances Data: 52691-62-0(Hazardous Substances Data)

Usage

Description

1-O-HEXADECYL-SN-GLYCERO-3-PHOSPHOCHOLINE, also known as Lyso-PAF C-16, is a white solid with unique chemical properties. It is formed through the action of PAF-AH on PAF C-16 or by the action of a CoA-independent transacylase on 1-O-hexadecyl-2-acyl-glycerophosphocholine. 1-O-HEXADECYL-SN-GLYCERO-3-PHOSPHOCHOLINE serves as a substrate for PAF C-16 formation through the remodeling pathway or selective acylation with arachidonic acid by a CoA-independent transacylase.

Uses

Used in Pharmaceutical Industry:
1-O-HEXADECYL-SN-GLYCERO-3-PHOSPHOCHOLINE is used as a substrate for the production of PAF C-16, which has potential applications in the development of drugs targeting various diseases. 1-O-HEXADECYL-SN-GLYCERO-3-PHOSPHOCHOLINE plays a crucial role in the synthesis of active platelet-activating factor (PAF), which is involved in numerous physiological and pathological processes, including inflammation, immune response, and blood clotting.
Used in Research and Development:
In the field of research and development, 1-O-HEXADECYL-SN-GLYCERO-3-PHOSPHOCHOLINE is utilized as a key intermediate in the study of PAF metabolism and its role in various biological processes. 1-O-HEXADECYL-SN-GLYCERO-3-PHOSPHOCHOLINE helps researchers understand the mechanisms of PAF synthesis and its potential as a therapeutic target for treating diseases associated with PAF dysregulation.
Used in Drug Delivery Systems:
1-O-HEXADECYL-SN-GLYCERO-3-PHOSPHOCHOLINE can be employed in the development of novel drug delivery systems, particularly for the targeted delivery of PAF C-16 or its analogs. These delivery systems aim to improve the bioavailability, efficacy, and safety of PAF-related therapeutics by enhancing their delivery to specific cells or tissues.
Used in Analytical Chemistry:
As a white solid with distinct chemical properties, 1-O-HEXADECYL-SN-GLYCERO-3-PHOSPHOCHOLINE can be used as a reference compound in analytical chemistry for the development and validation of methods for the detection and quantification of PAF and its metabolites in biological samples.

InChI:InChI=1/C24H52NO6P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-20-29-22-24(26)23-31-32(27,28)30-21-19-25(2,3)4/h24,26H,5-23H2,1-4H3/t24-/m1/s1

Upstream product

• 77286-68-1 3-O-hexadecyl-2-acetyl-sn-glycero-1-phosphocholine 
• 143516-78-3 ((R)-2-Hexadecyloxy-1-methoxymethoxymethyl-ethoxymethyl)-benzene 
• 1204817-45-7 1-O-hexadecyl-2-O-(4-methoxybenzyl)-sn-glycero-3-phosphocholine 
• 506-03-6 chimyl alcohol 
• 115406-33-2 1-O-hexadecyl-2-O-(3-isoxazolyl)-3-O-triphenylmethyl-sn-glycerol 
• 96093-53-7 (S)-3-(1-hexadecyloxy)-1-(trityloxy)propan-2-ol 
• 115406-32-1 1-O-hexadecyl-2-O-(3-isoxazolyl)-sn-glycerol 
• 91326-86-2 16-<(2S)-(2,3-(isopropylidenedioxy)propyl)oxy>hexadecane 
• 91274-00-9 2-bromoethyl 2-O-benzyl-L-1-O-hexadecyl-glyceryl hydrogen phosphate 
• 84379-55-5 1-O-hexadecyl-2-O-benzyl-3,4-O-isopropylidene-D-threitol 
• 84379-57-7 1-O-hexadecyl-2-O-benzyl-D-threitol 
• 96924-84-4 Phosphorochloridic acid (R)-2-benzyloxy-3-hexadecyloxy-propyl ester 2-bromo-ethyl ester 
• 20779-14-0 methanesulfonic acid hexadecyl ester 
• 166102-97-2 3-O-hexadecyl-2-O-benzyl-D-glyceraldehyde dimethylacetal 

Downstream Products

• 1159279-46-5 1-O-hexadecyl-2-(4-(4-(bis-(2-chloroethyl)amino)phenyl)butanoyl)-sn-glycero-3-phosphocholine 
• 74389-68-7 PAF 
• 88587-94-4 L-1-hexadecyl-2-palmitoyl-phosphatidylcholine 

Relevant articles and documents

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.

Synthesis and biological activity of anticancer ether lipids that are specifically released by phospholipase A2 in tumor tissue

The clinical use of anticancer lipids is severely limited by their ability to cause lysis of red blood cells prohibiting intravenous injection. Novel delivery systems are therefore required in order to develop anticancer ether lipids (AELs) into clinicall

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