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SDS, COA, datasheet, and spec sheet available for download. Lot-specific COA accessible via lot number lookup.
Cited in 282 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.
[2-(Methacryloyloxy)ethyl]dimethyl-(3-sulfopropyl)ammonium hydroxide (DMAPS) is a hygroscopic, zwitterionic monomer used in the synthesis of polysulfobetaines. Polysulfobetaines are electrically neutral polymers that contain both cationic and anionic groups within a single monomer unit and feature interesting properties such as antielectrolyte behavior in aqueous salt solutions, biocompatibility, and hemocompatibility. Based upon these properties, polysulfobetaines are useful in many biomedical applications such as drug delivery and drug formulation.
Application
Due to its hygroscopic nature, [2-(methacryloyloxy)ethyl]dimethyl-(3-sulfopropyl)ammonium hydroxide (DMAPS) can contain up to one molecule of water per monomer unit. This material should be stored in a cool, dry place and depending on the reaction conditions, water may need to be removed prior to polymerization.
| Pubchem Sid | 488194208 |
|---|---|
| Pubchem Sid Url | https://pubchem.ncbi.nlm.nih.gov/substance/488194208 |
| Canonical Smiles | CC(=C)C(=O)OCC[N+](C)(C)CCCS(=O)(=O)[O-] |
| IUPAC Name | 3-[dimethyl-[2-(2-methylprop-2-enoyloxy)ethyl]azaniumyl]propane-1-sulfonate |
| InChIKey | BCAIDFOKQCVACE-UHFFFAOYSA-N |
| INCHI | 1S/C11H21NO5S/c1-10(2)11(13)17-8-7-12(3,4)6-5-9-18(14,15)16/h1,5-9H2,2-4H3 |
| Isomeric SMILES | CC(=C)C(=O)OCC[N+](C)(C)CCCS(=O)(=O)[O-] |
| Molecular Weight | 279.35 |
| Reaxy-Rn | 4144613 |
| Reaxys-RN_link_address | https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=4144613&ln= |
Comprehensive hazard, handling, storage, and regulatory compliance document.
Download SDS →Lot-specific quality data. Enter your lot number to retrieve the exact COA.
Look up COA →Full quality attributes and acceptance criteria for this grade.
View spec sheet →Taxonomy Tree
| Kingdom | Organic compounds |
|---|---|
| Superclass | Organic nitrogen compounds |
| Class | Organonitrogen compounds |
| Subclass | Quaternary ammonium salts |
| Intermediate Tree Nodes | Cholines |
| Direct Parent | Acyl cholines |
| Alternative Parents | Tetraalkylammonium salts Sulfonyls Organosulfonic acids Enoate esters Alkanesulfonic acids Monocarboxylic acids and derivatives Organic salts Organic oxides Hydrocarbon derivatives Carbonyl compounds Amines Organic cations |
| Molecular Framework | Aliphatic acyclic compounds |
| Substituents | Acyl choline - Organic sulfonic acid or derivatives - Organosulfonic acid or derivatives - Organosulfonic acid - Sulfonyl - Alkanesulfonic acid - Enoate ester - Alpha,beta-unsaturated carboxylic ester - Tetraalkylammonium salt - Carboxylic acid ester - Carboxylic acid derivative - Monocarboxylic acid or derivatives - Carbonyl group - Amine - Organic oxygen compound - Organosulfur compound - Organic salt - Hydrocarbon derivative - Organooxygen compound - Organic oxide - Organic cation - Aliphatic acyclic compound |
| Description | This compound belongs to the class of organic compounds known as acyl cholines. These are acylated derivatives of choline. Choline or 2-Hydroxy-N,N,N-trimethylethanaminium is a quaternary ammonium salt with the chemical formula (CH3)3N+(CH2)2OH. |
| External Descriptors | Not available |
Find and download the COA for your product by matching the lot number on the packaging.
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| Certificate of Analysis | Apr 24, 2026 | M164461 | |
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| Sensitivity | Hygroscopic |
|---|---|
| Melt Point(°C) | 150-155°C |
| Molecular Weight | 279.360 g/mol |
| XLogP3 | 0.300 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 8 |
| Exact Mass | 279.114 Da |
| Monoisotopic Mass | 279.114 Da |
| Topological Polar Surface Area | 91.900 Ų |
| Heavy Atom Count | 18 |
| Formal Charge | 0 |
| Complexity | 381.000 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| The total count of all stereochemical bonds | 0 |
| Covalently-Bonded Unit Count | 1 |
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| 2. Anning Chen, Zhengao Wang, Hailun Chen, Bo Pang, He Cai, Ziheng Chen, Chengyun Ning, Dong Ma, Jie Tang, Hongzheng Zhang. (2023) Zwitterion modified cochlear implants resist postoperative infection and inflammation. Materials Today Bio, [PMID:38075255] [10.1016/j.mtbio.2023.100856] |
| 3. Liheng Xie, Yuexin Liang, Zhiyu Wang, Wentao Zhang, Fengjiao Guo, Xiaqing Chang, Hongyu Mi, Jieshan Qiu. (2023) Achieving a Reversible and Durable Zn Anode Using the Polyzwitterionic Hydrogel Electrolyte for Efficient Zn-Ion Energy Storage. ACS Applied Polymer Materials, [PMID:] [10.1021/acsapm.3c02124] |
| 4. Fei Long, Xinwen Zhang, Xuan Li, Fei Sun, Tong Zhou, Lei Liu. (2023) Ultrathin Water-Responsive Zwitterionic Hydrogel Brush Coatings for Long-Term Corrosion Protection. ACS Applied Materials & Interfaces, [PMID:38149814] [10.1021/acsami.3c13841] |
| 5. Mingzhu Zeng, Zhimao Huang, Xiao Cen, Yinyu Zhao, Fei Xu, Jiru Miao, Quan Zhang, Rong Wang. (2023) Biomimetic Gradient Hydrogels with High Toughness and Antibacterial Properties. Gels, 10 (1): (6). [PMID:38275844] [10.3390/gels10010006] |
| 6. Xiaobin Li, Jun Shi, Chenguang Kong, Cunzhi Li, Hangzhou Wang, Shumin Jiang, Yang Li. (2023) Photoinitiator-grafted polymer coating enable various hydrogels with strong resistance to both drying and swelling. CHEMICAL ENGINEERING JOURNAL, [PMID:] [10.1016/j.cej.2023.147937] |
| 7. Wenjing Ma, Wenxuan Cao, Min Cui, Haifeng Lu, Ranhua Xiong, Chaobo Huang. (2023) Biomass-derived 3D evaporator with antifouling and salt-rejecting toward solar-enabled steam generation, desalination, and electricity generation. CHEMICAL ENGINEERING JOURNAL, [PMID:] [10.1016/j.cej.2023.147404] |
| 8. Rui Gao, Caihong Liu, Andreia F. Faria, Qiang He, Chun Yang, Jun Ma. (2023) Designing a multifunctional TFC membrane with improved permeability and anti-biofouling performance using zwitterionic, quaternary ammonium, and fluorinated materials. JOURNAL OF MEMBRANE SCIENCE, [PMID:] [10.1016/j.memsci.2023.122241] |
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| 10. Yuan Zeting, Ma Shuli, Li Yue, Fang Haowei, Shang Jing, Zhan Yueping, Wang Jie, Chen Teng, Deng Wanli, Kunxi Zhang, Yin Peihao. (2023) Tissue adhesive indocyanine green-locking granular gel-mediated photothermal therapy combined with checkpoint inhibitor for preventing postsurgical recurrence and metastasis of colorectal cancer. Bioengineering & Translational Medicine, [PMID:38023716] [10.1002/btm2.10576] |
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| 12. Wenting Chen, Yikun Yi, Feng Hai, Zhendi Wu, Jingyu Guo, Xiaolu Tian, Xin Gao, Wei Tang, Mingtao Li. (2023) A Flexible and Self-Healing Ionic Gel Electrolyte Based on a Zwitterion (ZI) Copolymer for High-Performance Lithium Metal Batteries. Batteries-Basel, 9 (9): (452). [PMID:] [10.3390/batteries9090452] |
| 13. Leqi Wu, Sui Wang, Jie Mao, Zhiyong Guo, Yufang Hu. (2023) Dual network zwitterionic hydrogels with excellent mechanical properties, anti-swelling, and shape memory behaviors. EUROPEAN POLYMER JOURNAL, [PMID:] [10.1016/j.eurpolymj.2023.112373] |
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| 15. Hongjian Huang, Yan Fang, Yunxiang Weng, Haiqing Liu. (2023) Photo-/electro-chromic underwater adhesive coacervate from self-assembly of zwitterions and polyoxometalate. Materials Today Chemistry, [PMID:] [10.1016/j.mtchem.2023.101670] |
| 16. Juan Zeng, Hao Chen, Liubing Dong, Lu Wei, Xin Guo. (2023) Designing of zwitterionic proline hydrogel electrolytes for anti-freezing supercapacitors. JOURNAL OF COLLOID AND INTERFACE SCIENCE, [PMID:37633110] [10.1016/j.jcis.2023.08.037] |
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