67881-98-5

Basic information

• Product Name: 2-methacryloyloxyethyl phosphorylcholine
• Synonyms: Creatinol O-phosphate Magnesium;2-methacryloyloxyethyl phosphorylcholine;2-(Methacryloyloxy)ethyl 2-(Trimethylammonio)ethyl Phosphate;Phosphoric Acid 2-(Methacryloyloxy)ethyl 2-(Trimethylammonio)ethyl Ester;[2-[[2-(Methacryloyloxy)ethoxy]phosphonyloxy]ethyl]trimethylaminium;Methacrylic acid 2-[[[2-(trimethylaminio)ethoxy]phosphonyl]oxy]ethyl ester;O-[[2-(Methacryloyloxy)ethoxy]phosphonyl]choline;O-[[2-[(2-Methylpropenoyl)oxy]ethoxy]phosphonyl]choline
• CAS NO: 67881-98-5
• Molecular Formula: C₁₁H₂₂NO₆P
• Molecular Weight: 295.27
• Product Categories: Ammonium Polyhalides, etc. (Quaternary);Quaternary Ammonium Compounds
• Mol File: 67881-98-5.mol
• Article Data: 8

Chemical Properties

• Melting Point: 143-148°C
• Appearance: /
• Density: 1.22-1.41 at 21.5-22.4℃
• Vapor Pressure: 0-0Pa at 25℃
• Storage Temp.: 2-8°C
• Water Solubility: 83-86vol% at 20℃ and pH5.9-6.8[vol%]
• CAS DataBase Reference: 2-methacryloyloxyethyl phosphorylcholine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-methacryloyloxyethyl phosphorylcholine(67881-98-5)
• EPA Substance Registry System: 2-methacryloyloxyethyl phosphorylcholine(67881-98-5)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 1
• Hazardous Substances Data: 67881-98-5(Hazardous Substances Data)

Usage

Chemical Properties

White solid

Uses

MPC block copolymers with styrene are biocompatible in nature.

General Description

Methacryloyloxyethyl phosphorylcholine (MPC), containing a phosphorylcholine group in the side chain is a most suitable monomer to mimic the phospholipid polar groups contained with cell membranes. MPC block copolymers are biocompatible in nature; it shows desirable interaction with living tissues. It is hydroscopic in nature.

InChI:InChI=1/C11H22NO6P/c1-10(2)11(13)16-8-9-18-19(14,15)17-7-6-12(3,4)5/h1,6-9H2,2-5H3

Synthetic route

C11H23Br2NO6P(1+)*Cl(1-) → 2-methacryloyloxyethyl phosphorylcholine (67881-98-5)

Conditions	Yield
With zinc In ethanol at 0℃;	86%

Ethylene 2-(methacryloyloxy)ethyl phosphate (82793-19-9) + trimethylamine (75-50-3) → 2-methacryloyloxyethyl phosphorylcholine (67881-98-5)

Conditions	Yield
In acetonitrile at 50℃; for 48h; Ring cleavage; Amination;	37%
In acetonitrile at -20 - 60℃; for 36h;
In acetonitrile at -20 - 60℃; for 16h; Sealed tube;	3.1 g

2-Bromoethyl 2-cyanoethyl-2-(methacryloyloxy)ethyl phosphate (190070-82-7) + trimethylamine (75-50-3) → 2-methacryloyloxyethyl phosphorylcholine (67881-98-5)

Conditions	Yield
In acetonitrile at 75℃; for 24h; Amination;

2-methyl-2-propenoic acid 2-hydroxyethyl ester (868-77-9) → 2-methacryloyloxyethyl phosphorylcholine (67881-98-5)

Conditions	Yield
Multi-step reaction with 4 steps 1: N,N-diisopropylamine tetrazolide / dichloromethane / 0.33 h 2: 4,5-dichloroimidazole / acetonitrile / 16 h / 20 °C 3: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.17 h / 20 °C 4: acetonitrile / 24 h / 75 °C View Scheme
Multi-step reaction with 2 steps 1: triethylamine / tetrahydrofuran / 4 h / -30 - -20 °C 2: acetonitrile / 16 h / -20 - 60 °C / Sealed tube View Scheme

Ethylenedioxy-2-(methacryloyloxy)ethoxyphosphine (24619-52-1) → 2-methacryloyloxyethyl phosphorylcholine (67881-98-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: trimethylamine-N-oxide / acetonitrile / 0.67 h 2: acetonitrile / 48 h / 50 °C View Scheme

2-Bromoethoxy-2-(cyanoethoxy)-2-(methacryloyloxy)ethoxyphosphine (190070-81-6) → 2-methacryloyloxyethyl phosphorylcholine (67881-98-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.17 h / 20 °C 2: acetonitrile / 24 h / 75 °C View Scheme

2-((2-cyanoethoxy)(diisopropylamino)phosphinoxy)ethyl methacrylate (190070-80-5) → 2-methacryloyloxyethyl phosphorylcholine (67881-98-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: 4,5-dichloroimidazole / acetonitrile / 16 h / 20 °C 2: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.17 h / 20 °C 3: acetonitrile / 24 h / 75 °C View Scheme

2-methyl-2-propenoic acid 2-hydroxyethyl ester (868-77-9) + choline phosphoryl chloride → 2-methacryloyloxyethyl phosphorylcholine (67881-98-5)

Conditions	Yield
In acetonitrile

2,3-dibromo-2-methylpropionic acid hydroxyethyl ester → 2-methacryloyloxyethyl phosphorylcholine (67881-98-5)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: trichlorophosphate; triethylamine / acetonitrile / 2.5 h / -5 - 20 °C 2.1: triethylamine / 2 h / 0 - 20 °C 2.2: 1 h / 0 - 20 °C 3.1: zinc / ethanol / 0 °C View Scheme

Upstream product

• 868-77-9 2-methyl-2-propenoic acid 2-hydroxyethyl ester 
• 190070-80-5 2-Cyanoethoxy(diisopropylamino)-2-(methacryloyloxy)ethoxyphosphine 
• 190070-81-6 2-Bromoethoxy-2-(cyanoethoxy)-2-(methacryloyloxy)ethoxyphosphine 
• 24619-52-1 Ethylenedioxy-2-(methacryloyloxy)ethoxyphosphine 
• 190070-82-7 2-Bromoethyl 2-cyanoethyl-2-(methacryloyloxy)ethyl phosphate 
• 75-50-3 trimethylamine 
• 82793-19-9 Ethylene 2-(methacryloyloxy)ethyl phosphate 

Relevant articles and documents

Comprising orlistat nanosphere in use in the preparation of antineoplastic (by machine translation)

The invention relates to the field of medical technology, in particular to a containing orlistat nanosphere in use in the preparation of antineoplastic. The nanosphere comprises orlistat and selected from vitamin A methyl acrylate - 2 - methacryloyl ethyl choline phosphate copolymer or vitamin E methyl acrylate - 2 - methacryloyl ethyl choline phosphate copolymer or vitamin D2 Methyl acrylate - 2 - methacryloyl ethyl choline phosphate copolymer in the copolymer. The in vitro test result display, the present invention provides nano-microsphere to human prostate cancer cells DU145, black pigment tumor cell A375 with human pancreatic cancer cell strain bxpc - 3 anti-tumor activity significantly higher than to the orlistat alone, and than to adopt the PMB30W as carrier preparation of contrasting the nanosphere and containing orlistat and polyethylene glycol - polycaprolactone nanosphere of better anti-tumor activity. (by machine translation)

Orlistat nanosphere and application of same in preparation of obesity treatment drugs

The invention relates to the technical field of medicine, in particular to an orlistat nanosphere and application of the same in preparation of obesity treatment drugs. The nanosphere comprises orlistat and a copolymer, wherein the copolymer is selected from one of a vitamin-A methacrylate-2-methacryloyloxyethyl phosphorylcholine copolymer, a vitamin-E methacrylate-2-methacryloyloxyethyl phosphorylcholine copolymer or a vitamin-D2 methacrylate-2-methacryloyloxyethyl phosphorylcholine copolymer. The encapsulation efficiency of the nanosphere is 82.67-93.83%. Animal experiments show that the vitamin absorption level of rats after the nanosphere is taken by the rats orally is obviously higher than the vitamin absorption level of rats after the orlistat and vitamins are taken by the rats orally at the same time (at the interval of two hours), and is similar to the vitamin absorption level of rats after the vitamins are taken by the rats individually and orally under fasting, so that deficiency of fat-soluble vitamin due to oral administration of the orlistat can be make up effectively, and safety weight loss can be realized.

Synthetic method of artificial cytomembrane main ingredient 2-methacryloyloxy ethyl phosphorylcholine

The invention provides a synthetic method of artificial cytomembrane main ingredient 2-methacryloyloxy ethyl phosphorylcholine. The synthetic method comprises the following steps: (1) dissolving phosphorus oxychloride in acetonitrile, adding triethylamine at 0 to 10 DEG C, dropwise adding 2,3-dibromo-2-hydroxyethyl methacrylate, reacting at -10 to 0 DEG C, adding triethylamine and choline chloride to facilitate the reaction at -10 to 0 DEG C, and obtaining bromophosphorylcholine after the reaction is ended; and (2) dissolving the bromophosphorylcholine obtained in the step (1) in ethanol, adding zinc powder, severely stirring, and obtaining 2-methacryloyloxyethyl phosphorylcholine. By adopting the synthetic method, a synthetic route of the original 2-methacryloyloxyethyl phosphorylcholine is simplified, no treatment is needed after the purification during the synthetic route, and the next operation can be directly carried out; severe conditions in the synthetic route are avoided, high-end equipment is not needed, uncontrollable factors during the synthetic route are reduced; raw materials are easy to obtain, the price is low, the cost is reduced, the use of solvents and raw materials with large toxicity is avoided, and the green synthesis is realized; and a foundation is set for the industrialization of the 2-methacryloyloxyethyl phosphorylcholine.