730114

2-Methacryloyloxyethyl phosphorylcholine

contains ≤100 ppm MEHQ as inhibitor, 97%

• Synonym(s): MPC
• Empirical Formula (Hill Notation): C₁₁H₂₂NO₆P
• CAS Number: 67881-98-5
• Molecular Weight: 295.27
• MDL number: MFCD11112180
• UNSPSC Code: 12162002
• PubChem Substance ID: 329764541
• NACRES: NA.23

Properties

• Assay: 97%
• form: powder or crystals
• contains: ≤100 ppm MEHQ as inhibitor
• mp: 143-148 °C
• storage temp.: 2-8°C
• SMILES string: CC(=C)C(=O)OCCOP([O-])(=O)OCC[N+](C)(C)C
• InChI: 1S/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
• InChI key: ZSZRUEAFVQITHH-UHFFFAOYSA-N

Description

General description

2-Methacryloyloxyethyl phosphorylcholine (MPC) is a zwitterionic phosphorylcholine group-containing methacrylate monomer and is the most suitable monomer to mimic the phospholipid polar groups contained with cell membranes. It is also used in the preparations of a wide range of polymeric biomaterials because of its excellent resistance to nonspecific protein adsorption, biocompatibility, and low toxicity. It is also used to develop diverse molecular structures with adjustable properties using a range of polymerization methods, including living radical polymerization. Due to the reactivity of methacrylate, MPC-based materials have a wide range of applications in biomedical fields. Furthermore, MPC is also used as a monomer in the production of various polymeric materials for several applications such as medical devices, lithium-based batteries, contact lenses, drug delivery, wound dressings, and tissue engineering scaffolds.

Application

2-Methacryloyloxyethyl phosphorylcholine (MPC) can be used in the following applications:

• Use as a monomer to produce fully zwitterionic polymer networks in a solvate ionic liquid for use as a gel electrolyte in lithium-based batteries.
• Synthesis of polymer coatings for medical devices to prevent blood clotting and bacterial adhesion.
• Preparation of hydrogels for use as contact lens materials and wound dressing.
• Production of polymeric micelles and nanoparticles for drug delivery.
• Use as a monomer to prepare polymer-modified antifouling silicone hydrogel contact lenses. The addition of MPC forms a cell membrane-like structure on the contact lens and helps to prevent cell and bacterial adhesion on the surface.

Features and Benefits

• It has bioinert properties due to the presence of a zwitter ionic phosphorylcholine (PC) group in the side chain.
• It can build various molecular architectures with tunable properties.
• It has excellent resistance to cell adhesion, blood coagulation, and non-specific protein adsorption.

Safety Information

• Pictograms: GHS07
• Signal Word: Warning
• Hazard Statements: H317
• Precautionary Statements: P261 - P272 - P280 - P302 + P352 - P333 + P313 - P362 + P364
• Hazard Classifications: Skin Sens. 1
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 1