Phosphorylcholine

• CAS: 107-73-3
• Catalog Number: ACM107733
• Category: Main Products
• Molecular Weight: 219.60
• Molecular Formula: C₅H₁₅ClNO₄P
• Synonyms: Choline phosphate; N-Trimethyl-2-aminoethylphosphonate; o-Phosphocholine; phosphorylcholine; O-Phosphonocholine; O-phosphoryl choline
• IUPAC Name: phosphocholine
• Appearance: White powder or crystalline powder
• Exact Mass: 219.04300

Case Study

Phosphocholine Used in the Synthesis of Zwitterionic Polymer Thermogel Material

Ko D Y, et al. Biomacromolecules, 2015, 16(12), 3853-3862.

A new zwitterionic polymer was synthesized from phosphocholine (PC) and biocompatible polypropylene glycol (PPG). Due to the critical solution temperature (LCST) behavior of PPG and the low protein adsorption properties of zwitterionic PC, the PC-PPG-PC thermogel material is expected to become a temperature-sensitive biocompatible material. Furthermore, the zwitterionic PCPPG-PC thermogel can become a promising sustained delivery vehicle for biopharmaceuticals and cells.
Synthesis of PC-PPG-PC thermogel
· Poly(propylene glycol) (10.00 g, 3.70 mmol) and triethylamine (1.30 mL, 9.33 mmol) were dissolved in dried toluene (100 mL).
· Afterwards, 2-Chloro-2-oxo-1,3,2-dioxaphospholane (0.68 mL, 7.40 mmol) was added to the mixture, and the reaction was stirred at room temperature for 20 hours.
· The formed trimethylammnium chloride was filtered out, and the solvent was evaporated. The resulting products were dissolved in anhydrous acetonitrile (25 mL) in a pressure reactor submerged in a dry ice-acetone bath.
· Trimethylamine (0.88 mL, 9.38 mmol) was then introduced, and the sealed reactor was heated at 65 °C for 72 hours. After cooling to room temperature, any remaining trimethylamine and solvent were removed by evaporation.
· Following 24 hours of nitrogen bubbling, the products underwent purification by dialysis (cutoff molecular weight: 1000 Da) and subsequent lyophilization.

Polyvalent Choline Phosphate Aact as A Biomembrane Adhesive

Yu X, et al. Nature materials, 2012, 11(5), 468-476.

Choline phosphate (CP) is a phosphocholine group with the reverse orientation of phosphocholine (PC) but is actually the same. Modification of the dendrimer hyperbranched polyglycerol (HPG) with CP groups results in strong electrostatic binding of the polymer structure to cell surfaces and PC-containing liposomes. This CP-PC adhesion mechanism implies its application potential in areas such as tissue engineering, tissue sealants, and local drug delivery.
Synthesis of HPG functionalized with CP and PC
· The synthesis of HPG-CP and HPG-PC involved a click reaction between azido-functionalized HPG (HPG-N3) and alkyne-functionalized p-CP and p-PC intermediates.
· The p-PC intermediate, prop-2-ynyle phosphatidyl choline, was created by reacting propargyl alcohol, trimethylamine, and 2-chloro-2-oxo-1,3,2-dioxaphospholane in anhydrous acetonitrile, with trimethylamine serving as both a catalyst and reactant.
· The p-CP intermediate, prop-2-ynyle choline phosphate, was formed through a one-pot reaction involving dimethylamino 2-propyne, methanol, and 2-chloro-2-oxo-1,3,2-dioxaphospholane in anhydrous acetonitrile.
· HPG-CP and HPG-PC were then synthesized by reacting HPG-N3 with either p-CP or p-PC, copper sulphate pentahydrate, and sodium ascorbate in a mixed solvent at 22 °C. After stirring for 24 h, the reaction mixture was dialyzed against water, and the resulting HPG-CP and HPG-PC were recovered through lyophilization of the dialysate.

Custom Reviews

August 07, 2023

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Copolymer precursor material
The existence of phospholipid groups in phosphorylcholine makes it have bionic structure, and it can be used to prepare copolymers with medical purposes.

Custom Q&A

What is the primary use of phosphorylcholine ?

Choline phosphate is mainly used as a food additive, used as a quality improver for brewing products, added to synthetic sake, it can increase the aroma; it can stabilize amino acids and other components of sake; it can also be used as a seasoning to increase the freshness of dishes.

What's boiling point of phosphorylcholine ?

108-111 ℃

What is the form of phosphorylcholine ?

White crystalline or crystalline powder

How soluble is phosphorylcholine in organic reagents ?

Phosphorylcholine insoluble in general organic solvents such as benzene, chloroform and ether, slightly soluble in ethanol and acetone, soluble in methanol, easily soluble in water.

What is the method of preparation of phosphorylcholine ?

In a concentrated aqueous solution of ethylene oxide, choline is made by reacting trimethylamine with it at room temperature. Or in the presence of potassium hydroxide, using iodomethane to methylate ethanolamine at room temperature, to make choline. And then the choline made above, dissolved in methanol, Chemicalbook with phosphoric acid to neutralize choline methanol solution, can generate choline phosphate, after concentration, drying, can get the crude product choline phosphate. Then dissolve the crude product in methanol solution, and then add acetone, get precipitation, filtering and separation, can produce choline phosphate finished product.

How biotoxic is phosphorylcholine ?

LD5072g,/kg (mouse, oral).

What is the melting point of phosphorylcholine ?

200~205℃

How sensitive is phosphorylcholine ?

Phosphorylcholine is environmentally sensitive to humidity and is deliquescent

What are the medicinal properties and related applications of phosphorylcholine ?

Choline Phosphate is a medicine for hepatitis, which can participate in the synthesis of phospholipids, and has the effect of protecting liver, strengthening liver, promoting lipid metabolism and anti-fatty liver. It can accelerate methyl transfer, supply activated methyl and accelerate liver cell regeneration. Choline phosphate can also provide acetylcholine in the body, improve the camping Chemicalbook and function of the vegetative nerve; decompose histamine, so that the activity of histamine in the kidneys is enhanced, and it has a certain detoxification effect. Clinically Choline Phosphate is mainly used in the treatment of acute jaundice or non-jaundice hepatitis, chronic prolonged and active hepatitis; it is also used in the treatment of hepatotoxicity, hepatic fatty infiltration or steatohepatitis, and cirrhosis of the liver.

What are the storage conditions for phosphorylcholine ?

Phosphorylcholine should be stored at room temperature in an inert atmosphere.