107-73-3

Basic information

• Product Name: phosphorylcholine
• Synonyms: choline chloride O-(dihydrogen phosphate);phosphorylcholine;trimethyl[2-(phosphonooxy)ethyl]ammonium chloride;Choline phosphate;trimethyl-(2-phosphonooxyethyl)azanium;PHOSPHOCHOLINE;N,N,N-Trimethyl-2-(phosphonooxy)ethanaminium;O-Phosphonocholine
• CAS NO: 107-73-3
• Molecular Formula: C₅H₁₅NO₄P*Cl
• Molecular Weight: 219.6
• EINECS: 203-516-6
• Mol File: 107-73-3.mol

Chemical Properties

• Melting Point: 108-111 °C (decomp)
• Boiling Point: 103 °C(Press: 12 Torr)
• Appearance: /
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: Methanol (Slightly), Water (Sparingly)
• CAS DataBase Reference: phosphorylcholine(CAS DataBase Reference)
• NIST Chemistry Reference: phosphorylcholine(107-73-3)
• EPA Substance Registry System: phosphorylcholine(107-73-3)

Safety Data

• Hazardous Substances Data: 107-73-3(Hazardous Substances Data)

Usage

Uses

1. Pharmaceutical Industry:
Phosphorylcholine is used as an intermediate in the synthesis of Uridine Diphosphate Choline Ammonium Salt (U829930), which is a CDPcholine cholinephosphotransferase analog. This application is significant for the development of pharmaceutical compounds.
2. Medical Device Industry:
Phosphorylcholine is used as a surface treatment for pipeline devices, such as the Pipeline Shield. The treatment helps mitigate device material-related thromboembolic complications, improving the safety and efficacy of these medical devices.
Chemical Properties:
Phosphorylcholine chloride is an organic chloride salt that appears as a white crystal or crystalline powder with a slightly fishy odor. It has a melting point of 200-205°C (in a sealed tube) and is prone to deliquescence. It is insoluble in general organic solvents like benzene, chloroform, and ether, slightly soluble in ethanol and acetone, soluble in methanol, and easily soluble in water, with a 10% aqueous solution having a pH of 4.8-5.0.

Characteristics

Phosphorylcholine, unlike most of the choline esters, is very stable towards alkaline and acid hydrolytic agents; this stability is attributed to the betaine structure of the compound. It is hydrolysed by kidney, bone, and serum phosphatase.

Preparation

Phosphorylcholine was synthesised from choline chloride and phosphorus pentoxide, the solvent being 100 percent. phosphoric acid [phosphorylation method of Manaka, 1931]. 2.4 g choline chloride, dried over phosphorus pentoxide, were dissolved in 15 g. 100 per cent. phosphoric acid, the solution was heated at 70°C. in vacuo until evolution of HC1 ceased, and 5 g. phosphorus pentoxide were added. The mixture, which became homogeneous after a few minutes, was kept at 70°C. for 3 hours. The clear viscous solution was poured into 400c.c. of ice water, and a barium hydroxide solution, saturated at 50°C., was added until the solution showed a strongly alkaline reaction. At the end of the neutralisation a smell of trimethylamine appears. The barium phosphate was centrifuged, the excess of barium ions removed by carbon dioxide, the precipitate centrifuged, and the solution reduced in vacuo to a small volume. It still contained a certain amount of barium ions depending on the amount of negatively charged phosphorylcholine ions present. The latter is determined by the pH of the solution. The amount of barium ions present was determined in an aliquot part of the solution by precipitation with sulphuric acid, and the amount of n-sulphuric acid required for complete precipitation of the barium ions added.

Enzyme inhibitor

This choline phosphomonoester (FWzwitterion = 183.14 g/mol; CAS 107-73- 3), also known as choline phosphate and phosphorylcholine, is a key intermediate in the biosynthesis of many phospholipids. Both the free acid and the calcium salt are very soluble in water. The free acid is relatively stable in acidic conditions: only 15% is hydrolyzed in five hours in 1 M HCl at 100°C. Under alkaline conditions, there is complete hydrolysis after four hours by refluxing with barium hydroxide. The phosphocholine chloride calcium salt is stable for months at room temperature. Target(s): 1-alkyl-2-acetylglycerophosphocholine esterase, or platelet-activatingfactor acetylhydrolase; choline-sulfatase; choline sulfotransferase; ethanolamine kinase; ethanolamine-phosphate cytidylyltransferase; glutamate decarboxylase; glycerophosphocholine cholinephosphodiesterase; ornithine decarboxylase; phosphoethanolamine Nmethyltransferase; phosphoserine phosphatase; and sphingomyelin phosphodiesterase, or sphingomyelinase.

InChI:InChI=1/C5H14NO4P.ClH/c1-6(2,3)4-5-10-11(7,8)9;/h4-5H2,1-3H3,(H-,7,8,9);1H

Upstream product

• 67-48-1 choline chloride 
• 6153-56-6 oxalic acid dihydrate 
• 72556-74-2 phosphorylcholine chloride calcium salt tetrahydrate 
• 927-62-8 N,N-dimethylbutylamine 
• 4826-71-5 phosphorylcholine chloride, calcium salt 
• 1455-05-6 2-chloroethyl phosphorodichloridate 

Downstream Products

• 987-78-0 citicoline 
• 33818-15-4 cytidine 5'-diphosphocholine sodium salt 
• 28319-77-9 L-glycero-3-phosphorylcholine 
• 4826-71-5 phosphorylcholine chloride, calcium salt 
• 67-48-1 choline chloride 
• 34688-34-1 glycerolcholine phosphate 

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Relevant articles and documents

METHOD OF PREPARING CHOLINE ALFOSCERATE AND PHARMACEUTICAL COMPOSITION COMPRISING THE SAME

The present invention relates to a method for preparing choline alfoscerate. According to the method provided by the present invention, choline alfoscerate of high purity can be obtained in high yield, and a choline alfoscerate pharmaceutical formulation of excellent quality can be prepared using the same. In addition, the present invention is capable of obtaining high-purity choline alfoscerate in a high yield, as well as having excellent process efficiency as a preparation process is simple and short.COPYRIGHT KIPO 2021

Synthesis method for compound choline alfoscerate for promoting brain functions

The invention discloses a synthesis method for a compound choline alfoscerate for promoting brain functions. The synthesis method comprises the following steps: (1) enabling calcium phosphorylcholinechloride to react with oxalic acid to generate precipitate of phosphorylcholine chloride and oxalic acid; (2) enabling the phosphorylcholine chloride prepared in the step (1) to react with an alkali in a solvent so as to obtain a salt of the phosphorylcholine chloride; and (3) enabling the salt of the phosphorylcholine chloride to react with propylene glycol, so as to obtain choline alfoscerate. Raw materials of the synthesis method for the compound choline alfoscerate for promoting brain functions are low in price, low in cost and easy to obtain, the synthesis method is short in synthesis path and high in yield, the obtained product is high in chemical purity, all reactions need no special production equipment, the obtained intermediate and final products need no column chromatography orcrystallization purification, the production cost can be lowered, industrial amplified production can be facilitated, a high-purity product can be provided for the market, and thus high economic benefits can be met.

Phosphorus chloride of alkali acid radical gallbladder method for preparing calcium salt

The invention provides a preparation method of calcium phosphorylcholine chloride, and belongs to the technical field of preparing organic phosphorus compound intermediates. The preparation method comprises the following steps of: putting choline chloride and excess phosphorylation agent in a reaction kettle for a condensation reaction, wherein the obtained condensate liquid is phosphorylcholine chloride; firstly, dissolving phosphorylcholine chloride with water, then adding alum and excess calcium hydroxide to the aqueous solution of phosphorylcholine chloride, regulating the pH, generating crystals and precipitating, and carrying out filter pressing to obtain the clear filtrate; adding calcium chloride to the clear filtrate, concentrating until solid is separated out to obtain the concentrated solution, adding ethanol metered by weight to the concentrated solution, separating out crystals, freezing and filtering to obtain the filter cake, then washing the filter cake with ethanol, and drying to obtain the finished product calcium phosphorylcholine chloride. The preparation method provided by the invention has the advantages of saving the energy source, reducing the energy consumption, shortening the production period, improving the yield and reducing the production cost; the content of calcium phosphorylcholine chloride in the finished product is 99% to 102%; the preparation method meets the requirements of industrial green production.

CDP-Ethanolamine and CDP-Choline: One-pot synthesis and 31P NMR study

Herein we report a one-pot multi-step synthesis of the cofactors CDP-Ethanolamine and CDP-Choline starting from cytidine 5′-monophosphate and using commercially available and/or easily prepared reagents. While studying the 31P NMR spectrum of CDP-Ethanolamine, an unexpected characteristic for a pyrophosphate diester was observed as it showed a singlet or two doublets depending upon the pH. Therefore, further NMR studies were undertaken to investigate the pH dependence of the peak splitting pattern and measure the acid dissociation constants of the compounds.

PHOSPHORYLCHOLINE-BASED AMPHIPHILIC SILICONES FOR MEDICAL APPLICATIONS

Amphiphilic biomimetic phosphorylcholine-containing silicone compounds for use in both topical and internal applications as components in biomedical devices. The silicone compounds, which include zwitterionic phosphorylcholine groups, may be polymerizable or non-polymerizable. Specific examples of applications include use as active functional components in ophthalmic lenses, ophthalmic lens care solutions, liquid bandages, wound dressings, and lubricious and anti-thrombogenic coatings.

A PROCESS FOR PREPARATION OF L-ALPHA-GLYCEROPHOSPHORYL CHOLINE

The present invention relates to a process for preparing L-α- glycerophosphorylcholine by reacting phosphocholine chloride to R-(+)-glycidol. The present invention can prepare a compound of formula 1 in short reaction step and high yield.