3-[[2-(Methacryloyloxy)ethyl]dimethylammonio]propionate
[CAS 24249-95-4]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: 3-[[2-(Methacryloyloxy)ethyl]dimethylammonio]propionate
• Synonyms: 3-[dimethyl-[2-(2-methylprop-2-enoyloxy)ethyl]azaniumyl]propanoate
• Molecular Formula: C₁₁H₁₉NO₄
• Molecular Weight: 229.27
• CAS Registry Number: 24249-95-4
• SMILES: CC(=C)C(=O)OCC[N+](C)(C)CCC(=O)[O-]

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P301+P312-P302+P352-P304+P340-P305+P351+P338

Discovery and Applications

3-[[2-(Methacryloyloxy)ethyl]dimethylammonio]propionate is a zwitterionic methacrylate derivative belonging to the class of betaine-type monomers. The molecule contains a polymerizable methacrylate group linked through an ester bond to a quaternary ammonium moiety, which is internally balanced by a carboxylate group. Compounds of this type are widely used as functional monomers in polymer chemistry because they combine vinyl polymerization capability with ionic character, enabling the formation of polymers with unique hydration, biocompatibility, and surface properties.

The development of zwitterionic monomers such as 3-[[2-(methacryloyloxy)ethyl]dimethylammonio]propionate is closely associated with advances in polymer and biomaterials science in the twentieth century. As researchers sought materials with improved compatibility with aqueous environments and biological systems, attention turned to monomers that carry both positive and negative charges within the same molecule. These betaine-like structures were found to exhibit strong hydration behavior and resistance to nonspecific protein adsorption, making them valuable in biomedical applications.

The structure of this compound is based on a methacrylate backbone, which is capable of undergoing free-radical polymerization. The methacryloyloxy group allows the molecule to be incorporated into a wide range of polymeric architectures, including homopolymers and copolymers with other vinyl monomers. This polymerizable functionality is a key feature that enables the design of materials with tailored surface and bulk properties.

Attached to the methacrylate group is a 2-(dimethylammonio)ethylpropionate zwitterionic side chain. This segment contains a quaternary ammonium center, which carries a permanent positive charge, and a carboxylate group, which carries a negative charge. The internal charge balance results in a zwitterionic structure that strongly interacts with water molecules through electrostatic and hydrogen-bonding interactions. This hydration behavior is a defining characteristic of betaine-type polymers.

Polymers derived from this monomer are part of a broader class of zwitterionic materials that have been extensively studied for their antifouling properties. Such materials resist adsorption of proteins, cells, and other biological species, which makes them useful in biomedical coatings, medical devices, and biosensor surfaces. The strong hydration layer formed around zwitterionic groups is considered to be responsible for this resistance to biofouling.

In addition to antifouling behavior, polymers containing this monomer can exhibit high water solubility and responsiveness to ionic strength. These properties arise from the ionic nature of the side chain and its interaction with surrounding solvent molecules. As a result, materials based on this monomer have been investigated in hydrogel formulations and aqueous polymer systems.

The synthesis of 3-[[2-(methacryloyloxy)ethyl]dimethylammonio]propionate is typically achieved through quaternization of a tertiary amine-containing methacrylate precursor, followed by introduction of the carboxylate functionality. Such synthetic strategies are common in the preparation of zwitterionic monomers, where controlled functional group placement is necessary to achieve the desired balance of charge and polymerizability.

From a materials science perspective, this monomer is important because it enables the design of polymers that combine mechanical stability from the methacrylate backbone with highly hydrated, ionic side chains. These combined properties have led to applications in hydrogels, surface coatings, and biomaterial interfaces where resistance to fouling and compatibility with biological fluids are required.

Overall, 3-[[2-(methacryloyloxy)ethyl]dimethylammonio]propionate is a zwitterionic methacrylate monomer that serves as a building block for functional polymers. Its significance lies in its ability to impart strong hydration, ionic character, and antifouling properties to polymer systems while retaining the versatile polymerization behavior of methacrylate-based materials.

References

2025. Invention and global impact of bioinspired 2-methacryloyloxyethyl phosphorylcholine polymers: molecular design, functions, and implementation in medical devices. Polymer Journal.
DOI: 10.1038/s41428-025-01109-6