107-73-3 Usage
Description
Phosphorylcholine (abbreviated ChoP) is the hydrophilic polar head group of some phospholipids, which is composed of a negatively charged phosphate bonded to a small, positively charged choline group. It is a choline ester which forms a part of the phosphatide molecule, and as such occurs in nearly all organs. It probably often exists in the free state, being liberated from the phosphatides by enzymic hydrolysis.
Chemical Properties
White crystal or crystalline powder, slightly fishy odor. Melting point 200～205°C(sealed tube). Has deliquescence. Insoluble in general organic solvents such as benzene, chloroform and ether, slightly soluble in ethanol and acetone, soluble in methanol, easily soluble in water, 10% aqueous solution pH=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.
Uses
Phosphocholine is an intermediate in the synthesis of Uridine Diphosphate Choline Ammonium Salt (U829930), which is CDPcholine cholinephosphotransferase analog. Pipeline device with Phosphorylcholine surface treatment (Pipeline Shield) could mitigate device material related thromboembolic complications.
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.
Definition
ChEBI: Phosphorylcholine chloride is an organic chloride salt comprising a choline phosphate cation and chloride anion. It contains a phosphocholine and a chloride.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 107-73-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 7 respectively; the second part has 2 digits, 7 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 107-73:
(5*1)+(4*0)+(3*7)+(2*7)+(1*3)=43
43 % 10 = 3
So 107-73-3 is a valid CAS Registry Number.
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
107-73-3Relevant articles and documents
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Cherbuliez,Rabinowitz
, p. 1154 (1959)
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Synthesis method for compound choline alfoscerate for promoting brain functions
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Paragraph 0023-0028, (2019/11/21)
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.
CDP-Ethanolamine and CDP-Choline: One-pot synthesis and 31P NMR study
Ghezal, Salma,Thomasson, Maggie S.,Lefebvre-Tournier, Isabelle,Périgaud, Christian,Macnaughtan, Megan A.,Roy, Béatrice
supporting information, p. 5306 - 5310 (2015/01/16)
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.
