N-Succinimidyl Acrylate - ≥98%(GC) , CAS No.38862-24-7

CAS: 38862-24-7 Cat. No.: N159034 Molecular Weight: 169.14 EC Number: 621-860-9

GRADE & PURITY ≥98%(GC)

Synonyms

1-(Acryloyloxy)-2,5-pyrrolidinedione | 2,5-Dioxopyrrolidin-1-yl acrylate | N-Acryloxysuccinimide | Acrylic Acid N-Succinimidyl Ester | N-Acryloyloxysuccinimide | Acrylic acid N-hydroxysuccinimide ester | (2,5-dioxopyrrolidin-1-yl) prop-2-enoate

Storage

Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

Overview

Acrylic acid N-hydroxysuccinimide ester (NAS) is a general acrylating agent that is used in the synthesis of:
Acrylated hyaluronic acid (HA) hydrogel for bone regeneration applications.
Injectable, biodegradable, and thermosensitive copolymers for tissue engineering.
Imidazole-based biocompatible, aqueous quantum dots (QDs).

Specifications

Synonyms

1-(Acryloyloxy)-2, 5-pyrrolidinedione | 2, 5-Dioxopyrrolidin-1-yl acrylate | N-Acryloxysuccinimide | Acrylic Acid N-Succinimidyl Ester | N-Acryloyloxysuccinimide | Acrylic acid N-hydroxysuccinimide ester | (2, 5-dioxopyrrolidin-1-yl) prop-2-enoate

Specifications & Purity

≥98%(GC)

Storage

Store at -20°C, Argon charged

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥98%(GC)

Names and Identifiers

• Pubchem Sid: 504757710
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504757710
• Canonical Smiles: C=CC(=O)ON1C(=O)CCC1=O
• IUPAC Name: (2,5-dioxopyrrolidin-1-yl) prop-2-enoate
• InChIKey: YXMISKNUHHOXFT-UHFFFAOYSA-N
• INCHI: 1S/C7H7NO4/c1-2-7(11)12-8-5(9)3-4-6(8)10/h2H,1,3-4H2
• Isomeric SMILES: C=CC(=O)ON1C(=O)CCC1=O
• Molecular Weight: 169.14
• Reaxy-Rn: 1528213
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1528213&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Pyrrolidines
      • Subclass Pyrrolidones

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Pyrrolidines
• Subclass: Pyrrolidones
• Intermediate Tree Nodes: Not available
• Direct Parent: Pyrrolidine-2-ones
• Alternative Parents: Dicarboximides Acrylic acids and derivatives Lactams Carboxylic acid salts Monocarboxylic acids and derivatives Azacyclic compounds Organopnictogen compounds Organonitrogen compounds Organic salts Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic heteromonocyclic compounds
• Substituents: 2-pyrrolidone - Dicarboximide - Acrylic acid or derivatives - Lactam - Carboxylic acid salt - Azacycle - Monocarboxylic acid or derivatives - Carboxylic acid derivative - Carbonyl group - Organic oxide - Hydrocarbon derivative - Organic salt - Organic nitrogen compound - Organooxygen compound - Organonitrogen compound - Organopnictogen compound - Organic oxygen compound - Aliphatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as pyrrolidine-2-ones. These are pyrrolidines which bear a C=O group at position 2 of the pyrrolidine ring.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Solubility: Soluble in Toluene
• Sensitivity: Moisture sensitive.&heat sensitive
• Melt Point(°C): 71 °C
• Molecular Weight: 169.130 g/mol
• XLogP3: -0.200
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 169.038 Da
• Monoisotopic Mass: 169.038 Da
• Topological Polar Surface Area: 63.700 Ų
• Heavy Atom Count: 12
• Formal Charge: 0
• Complexity: 242.000
• 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

References

1. Jia-Qi Hu, Jing Wang, Zhen-Hua Shen, Yu-Xian Lai, Jia-Yin You, Qiang Yan, Ke-Feng Ren, Jian Ji.  (2023)  Mechanical Enhancement of the Gelatin/Poly(zinc acrylate) Hydrogel Stent in Bile.  ACS Applied Bio Materials,      [PMID:37983123] [10.1021/acsabm.3c00786]

2. Yao-Yu Pan, Bai-Chuan Zhao, Xin Zhang, Wei Zhu, Ai-Guo Shen.  (2023)  “Dramatic Growth” of Microbial Aerosols for Visualization and Accurate Counting of Bioaerosols.  ANALYTICAL CHEMISTRY,      [PMID:37653720] [10.1021/acs.analchem.3c02042]

3. Xin Wei, Jun-Yang Wang, Xue Yang, Jin-Yong Wu, Rui Hong, Yuwei Liu, Juxiang Gou, Jia Hu, Ka Li, Lingli Li, Jia-Zhuang Xu, Zhong-Ming Li.  (2023)  Wet adhesion enhancement through citric-acid-regulated supramolecular network.  COMPOSITES PART B-ENGINEERING,      [PMID:] [10.1016/j.compositesb.2023.110964]

4. Yan Niu, Gongwei Tian, Cuiyuan Liang, Tianchi Wang, Xu Ma, Guifen Gong, Dianpeng Qi.  (2022)  Thermal-Sinterable EGaIn Nanoparticle Inks for Highly Deformable Bioelectrode Arrays.  Advanced Healthcare Materials,  12  (10): (2202531).  [PMID:36562213] [10.1002/adhm.202202531]

5. Mingchuan Yu, Di Wang, Da Zhong, Weichang Xie, Jun Luo.  (2022)  Adropin Carried by Reactive Oxygen Species-Responsive Nanocapsules Ameliorates Renal Lipid Toxicity in Diabetic Mice.  ACS Applied Materials & Interfaces,      [PMID:35951354] [10.1021/acsami.2c06957]

6. Xing-wang Wang, Jing Wang, Yan Yu, Lu Yu, You-xiang Wang, Ke-feng Ren, Jian Ji.  (2022)  A polyzwitterion-based antifouling and flexible bilayer hydrogel coating.  COMPOSITES PART B-ENGINEERING,      [PMID:] [10.1016/j.compositesb.2022.110164]

7. Yunting Zhang, Min Jiang, Guangsheng Du, Xiaofang Zhong, Chunting He, Ming Qin, Yingying Hou, Rong Liu, Xun Sun.  (2022)  An antigen self-assembled and dendritic cell-targeted nanovaccine for enhanced immunity against cancer.  Acta Pharmaceutica Sinica B,      [PMID:37655327] [10.1016/j.apsb.2022.03.017]

8. Qingyi Wei, Ting Liu, Hongbin Pu, Da-Wen Sun.  (2020)  Determination of acrylamide in food products based on the fluorescence enhancement induced by distance increase between functionalized carbon quantum dots.  TALANTA,      [PMID:32797907] [10.1016/j.talanta.2020.121152]

9. Zhiwu Chen, Xingxing Liang, Rui Yang, Miao Yang, Tianwei Tan, Hui Cao.  (2019)  Construction of ordered multienzyme systems using multifunctional polymer brush-grafted magnetic nanoparticles as scaffolds.  COLLOIDS AND SURFACES A-PHYSICOCHEMICAL AND ENGINEERING ASPECTS,      [PMID:] [10.1016/j.colsurfa.2019.123920]

10. Jinxie Zhang, Xudong Zhang, Gan Liu, Danfeng Chang, Xin Liang, Xianbing Zhu, Wei Tao, Lin Mei.  (2016)  Intracellular Trafficking Network of Protein Nanocapsules: Endocytosis, Exocytosis and Autophagy.  Theranostics,      [PMID:27698943] [10.7150/thno.16587]

11. Zhenglin Chen, Jiaqi Yang, Zhicheng Du, Jiansong Ji, Likun Zhang, Haifei Guan, Zhengyang Lei, Xiaopeng Zhang, Canhui Yang, Ying Zhu, Qianhui Sun, Lulu Xu, Ke Lin, Yuchen Wang, Chuhui Wang, Chong Zhang, Dongmei Yu, Peiwu Qin, Can Yang Zhang.  (2024)  A conductive and anti-freezing gelatin-PAA-based organic hydrogel (PC-OH) with high adhesion and self-healing activities for wearable electronics.  CHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.cej.2024.152465]

12. Hanjie Shao, Junjie Deng, Zeping Xu, Jiujun Zhu, Wei Jian, Peiru Zhang, Xinhua Zhou, Xie Zhang, Hao She, Jingyun Ma, Xiang Wu, Hong Li.  (2024)  A Janus hydrogel that enables wet tissue adhesion and resists abdominal adhesions.  Materials Today Bio,      [PMID:39318376] [10.1016/j.mtbio.2024.101248]

13. Ziyuan Zeng, Jiaming Zhang, Yige Gao, Yuanyuan Song, Luoming Liu, Miaomiao Zhu, Wenjing Ma, Jiajun Fu, Dongyang Miao, Chaobo Huang, Ranhua Xiong.  (2024)  Bioadhesive First-Aid Patch with Rapid Hemostasis and High Toughness Designed for Sutureless Sealing of Acute Bleeding Wounds.  Advanced Healthcare Materials,      [PMID:39520362] [10.1002/adhm.202403412]

14. Ran Yan, Zeqian Xu, Haokun Yi, Chaoran Xu, Hui Xu, Xuanyu Qi, Xiaoru Dong, Cheng Hu, Zhuo Li, Xinquan Jiang.  (2025)  Bioinspired Janus Universal Adhesive Patch: Bridging the Contrasting Interface of Soft Tissues and Medical Devices.  ADVANCED FUNCTIONAL MATERIALS,      [PMID:] [10.1002/adfm.202422130]

15. Shuaimin Tang, Pengzhou Cheng, Hanzhang Liang, Dongyong Sha, Lingfei Zhao, Ding Ding, Gongshen Liu, Changsheng Liu, Yiwei Liu, Yifan Ma, Yuan Yuan.  (2025)  Deep-Learning Integrated Bioelectronic-Tissue Interface for Cardiovascular Diagnosis and Prognosis.  ADVANCED FUNCTIONAL MATERIALS,      [PMID:] [10.1002/adfm.202423264]

16. Zhanzhan Zhang, Zheng Pan, Qiushi Li, Qingqing Huang, Linqi Shi, Yang Liu.  (2024)  Rational design of ICD-inducing nanoparticles for cancer immunotherapy.  Science Advances,  10  (6):   [PMID:38324678] [10.1126/sciadv.adk0716]

17. Chenyang Li, Yang Qian, Xueping Zhang, Rongwu Wang.  (2025)  Robust-adhesion and high-mechanical strength hydrogel for efficient wet tissue adhesion.  Journal of Materials Chemistry B,  13  (7): (2469-2479).  [PMID:39829313] [10.1039/D4TB02357A]

18. linna Zhang, Guofei Yu, Rui Dai, Shuang Wang, Min Yang, Haibo Wang.  (2025)  Self-adaptive adhesive, mechanically enhanced, and antibacterial non-woven fabric wound dressing functionalized by semi-interpenetrating network hydrogel for promoting infected wound healing†.  Journal of Materials Chemistry B,      [PMID:40189935] [10.1039/D4TB02851A]

19. Bing Xu, Liu Yang, Yan Li, Chunyu Cao.  (2025)  Sensitivity enhancement of fiber-optic SMOX sensor using gold film-AuNPs-antibody three layers structure.  OPTICAL MATERIALS,      [PMID:] [10.1016/j.optmat.2025.116876]

20. Juntao Zhang, Longxue Qiu, Haofei Xu, Yang Liu, Benmei Wei, Huizhi Kou, Chengzhi Xu, Lian Zhu, Haibo Wang.  (2025)  Regulation of the hemostatic performance of collagen: On the role of hydrophilicity.  CHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.cej.2025.168571]

21. Yuze Luo, Haowen Zhang, Ying Wang, Cheng Jin, Huimin Wang, Zefeng Wang, Yinbang Zheng, Huixu Zhou, Junqin Li, Chunlei Ou, Dinggeng He, Luo Hai.  (2025)  Macrophage-mimetic living hydrogel microspheres capable of generating NO via the cascade reaction between glucose oxidase and horseradish peroxidase for the treatment of diabetic wound infection.  INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES,      [PMID:40987355] [10.1016/j.ijbiomac.2025.147824]

22. Zihan Ma, Chengde Liu, Yizheng Li, Xigao Jian.  (2025)  Adhesive Gelatin/Chitosan Hydrogel Coating Containing MgO Nanoparticles for Promoting Soft Tissue Integration.  MACROMOLECULAR BIOSCIENCE,      [PMID:40982591] [10.1002/mabi.202500231]

23. Lu Zhengnan, Wang Yi, Zhang Peng, Sheng Yang, Sun Yixin, Bradley Mark, Zhang Rong.  (2025)  Design and in vitro photodynamic evaluation of self-illuminating nanospheres loaded with polyurethane containing protoporphyrin IX for anticancer and antibacterial applications.  JOURNAL OF MATERIALS SCIENCE,      [PMID:] [10.1007/s10853-025-11465-6]

24. Jiachun Wang, Juntao Hu, Wantong Jiang, Dongwei Zhu, Yinuo Yin, Yu Qin, Ao Song, Yibing Huang, Quan Luo.  (2025)  Mechanistic insights into redox-protonation coupled fluorescence switching in peptide-mediated gold nanoclusters for precision tumor imaging and resection.  JOURNAL OF COLLOID AND INTERFACE SCIENCE,      [PMID:40749287] [10.1016/j.jcis.2025.138582]

25. Dejun Lu, Yunchao Hao, Zhiqiao Wang, Jun He, Xiaojiang Huang, Yunxiang Shi, Shuai Gao, Huiqing Zhang, Yue Ma, Feng Xu, Yao Yao.  (2025)  Zn-PAA-C hydrogel for integrated energy storage and self-diagnostic health monitoring in wearable biomedical devices.  Energy Storage Materials,      [PMID:] [10.1016/j.ensm.2025.104407]

26. Zineng Yi, Xuan Zhang, Zhengbao Zha.  (2025)  Barnacle-Inspired Nanocomposite Paste with Enhanced Toughness and Crack Blunting for Rapid Hemostasis.  ADVANCED FUNCTIONAL MATERIALS,      [PMID:] [10.1002/adfm.202525065]

27. Yongyuan Kang, Xiaoqing Liu, Jie Wang, Pai Peng, Min Liang, Qiaoxuan Wang, Weiwei Zheng, Shifen Li, Changyou Gao.  (2025)  Rod-Shaped Microgel Scaffolds with Interconnective Pores and Oxygen-generating Functions Promote Skin Wound Healing and Alleviate Hypertrophic Scar Formation.  ADVANCED FUNCTIONAL MATERIALS,      [PMID:] [10.1002/adfm.202413678]

28. Sun Xiangyu, Cheng Cheng, Zhang Jinxie, Jin Xing, Sun Shuqing, Mei Lin, Huang Laiqiang.  (2019)  Intracellular Trafficking Network and Autophagy of PHBHHx Nanoparticles and their Implications for Drug Delivery.  Scientific Reports,  9  (1): (1-10).  [PMID:31270337] [10.1038/s41598-019-45632-y]

29. Xiaoxue Hou, Chun Wang, Yu Zhao, Qian Wang, Dianyu Wang, Jingyu Zhao, Yang Liu, Fan Huang, Jianfeng Liu.  (2025)  Tumor-Specific Activated Polymeric Nanotuners Disrupt Positive Feedback Cycle of Hypoxia and Apoptosis Evasion for Potent Cancer Radiotherapy.  BIOMATERIALS,      [PMID:40279765] [10.1016/j.biomaterials.2025.123361]

30. Shengyu Liu, Yi Wang, Sijia Yao, Qian Li, Chenkai Sun, Yishan Chen, Junqiu Ye, Weisong Li, Dong Wu, Jianping Zhou, Hao Cheng, Yang Ding.  (2025)  Combinative dual-nanoparticle assembly improves oxygen-autarky PDT efficacy in hypoxic tumors.  CHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.cej.2025.163836]

31. Xiaowei Liu, Haojie Yu, Li Wang, Ruixue Liang, Yanxin Xiang, Xiaohang Song, Ying Yang, Zhikun Huang, Jian Yang, Di Shen, Yan Sheng.  (2025)  Body-temperature responsive hydrogel adhesive for active wound closure.  Journal of Materials Chemistry B,      [PMID:40454430] [10.1039/D5TB00084J]

32. Jianhui Chen, Gongwei Tian, Dan Yang, Cuiyuan Liang, Hua Liu, Ruiwen Tian, Weihong Lu, Yan Liu, Dianpeng Qi.  (2025)  Coffee Ring Effect Induced Selective Wetting of Liquid Metal for High-Resolution Stretchable Bioelectrodes.  ACS Applied Materials & Interfaces,      [PMID:40512557] [10.1021/acsami.5c06655]

33. Ning Jia, Liu Yu, Hongfang Meng, Sitian Liu, Zhuosheng Lin, Ting Li, Ling Wang, Wenhua Huang, Yaobin Wu.  (2025)  Laminin-conjugated aligned nanofiber yarns for topographical and biochemical guidance of neurite outgrowth and branching regulation.  JOURNAL OF NANOBIOTECHNOLOGY,      [PMID:41353422] [10.1186/s12951-025-03909-7]

34. Xinghui Gao, Rongbai Ju, Siyuan Zhang, Ouzile Chen, Fangjun Huo, Min He, Weidong Tian.  (2025)  Janus Bilayer Hydrogel Dressing With Enhanced Long-Term Wet Adhesion via Physical-Covalent Synergistic Mechanism for Oral Mucosal Wound Healing.  Advanced Healthcare Materials,      [PMID:41408926] [10.1002/adhm.202504498]

35. Hao She, Hanjie Shao, Weiqin Chen, Yang Zhou, Jingyun Ma, Zeping Xu, Jun Li, Xinhua Zhou, Xiang Wu, Hong Li.  (2025)  A Multifunctional Bilayer Hydrogel for Effective Pancreatic Fistula Prevention and Post-Surgical Adhesion Control.  Advanced Healthcare Materials,      [PMID:41388685] [10.1002/adhm.202503972]

36. Fangyuan Zhao, Guoqin Ma, Yuqi Zhang, Mengfei Jiang, Makesh Mohan, Qingsong Zhang, Zhongyu Cai.  (2025)  A universal protein immobilization method to construct responsive photonic hydrogels with enhanced sensing performance.  JOURNAL OF COLLOID AND INTERFACE SCIENCE,      [PMID:41455268] [10.1016/j.jcis.2025.139747]

37. Yutang Ding, Kun Tang, Yuheng Zhang, Linxin Yang, Binjing Zhang, Xin Zhang, Jian Wang.  (2025)  Sustained copper-releasing adhesive hydrogel patch promotes optimized scarless tongue wound healing via antioxidative, angiogenic and antifibrotic synergy.  Journal of Materials Chemistry B,      [PMID:41553251] [10.1039/D5TB02753E]

38. Lan Yuqun, Li Shuang, Guo Haitao, Liu Qinyuan, Wang Tairan, Zhou Lianqiao, Fang Jiahuiyu, Zhao Yang, Zhou Zanxin, Wang Qi, Li Jing, Zhu Yiping, Su Rongfang, Wen Xinyi, Xu Xinkai, Wu Yuhong, Wang Zixuan, Liu Bo, Li Jiaqi, Li Hui, Gao Hanfei, Wu Yuchen, Gu Qi, Feng Xi-Qiao, Yu Xinge, Su Yewang.  (2026)  Soft biodegradable implants for long-distance and wide-angle sensing.  NATURE,  649  (8096): (366-374).  [PMID:41501198] [10.1038/s41586-025-09874-3]

39. Jia Li, Li Xiao, Qun Li, Zhixin Zhao, Yuan Wang, Leixiao Yu.  (2026)  Mechanically promotes diabetic wound healing via restoring wound contractility.  CHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.cej.2026.175726]