4-Maleimidobutyric Acid - ≥98% , CAS No.57078-98-5

CAS: 57078-98-5 Cat. No.: M122236 Molecular Weight: 183.16 Beilstein Registry Number: 1455876 EC Number: 611-461-8

GRADE & PURITY ≥98%

Synonyms

M2337 | 4-(2,5-dioxo-2H-pyrrol-1(5H)-yl)butanoic acid | 4-Maleimidobutyric acid | 4-Maleimidobutyric acid, >=98.0% (T) | BP-21999 | A8148 | 1H-Pyrrole-1-butanoic acid, 2,5-dihydro-2,5-dioxo- | 4-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)butanoic acid;4-Maleim

Storage

Store at 2-8°C,Argon charged

Shipped In

Wet ice

Application

227,228,229

Overview

Gamma-maleimidobutyric acid may be used as a spacer in the construction of drug and other types of bioconjugates. 4-Maleimidobutyric acid is used with N-hydroxysuccinimide ester as a bifunctional cross-linking agent. Modification reagent for thiol groups in proteins

Specifications

Synonyms

M2337 | 4-(2, 5-dioxo-2H-pyrrol-1(5H)-yl)butanoic acid | 4-Maleimidobutyric acid | 4-Maleimidobutyric acid, >=98.0% (T) | BP-21999 | A8148 | 1H-Pyrrole-1-butanoic acid, 2, 5-dihydro-2, 5-dioxo- | 4-(2, 5-dioxo-2, 5-dihydro-1H-pyrrol-1-yl)butanoic acid;4-Maleim

Specifications & Purity

≥98%

Biochemical and Physiological Mechanisms

SH-label for the modification of peptides and proteins1; Used for the preparation of a new bleomycin analog for enzyme immunoassay (EIA); probe for membrane SH-groups

Storage

Store at 2-8°C, Argon charged

Shipped In

Wet ice

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

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 488194386
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488194386
• Canonical Smiles: C1=CC(=O)N(C1=O)CCCC(=O)O
• IUPAC Name: 4-(2,5-dioxopyrrol-1-yl)butanoic acid
• InChIKey: NCPQROHLJFARLL-UHFFFAOYSA-N
• INCHI: 1S/C8H9NO4/c10-6-3-4-7(11)9(6)5-1-2-8(12)13/h3-4H,1-2,5H2,(H,12,13)
• Isomeric SMILES: C1=CC(=O)N(C1=O)CCCC(=O)O
• WGK Germany: 3
• Molecular Weight: 183.16
• Beilstein: 1455876
• Reaxy-Rn: 1455876
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1455876&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Fatty Acyls
      • Subclass Fatty acids and conjugates

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Fatty Acyls
• Subclass: Fatty acids and conjugates
• Intermediate Tree Nodes: Not available
• Direct Parent: Heterocyclic fatty acids
• Alternative Parents: Maleimides N-substituted carboxylic acid imides Pyrrolines Dicarboximides Monocarboxylic acids and derivatives Carboxylic acids Azacyclic compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic heteromonocyclic compounds
• Substituents: Heterocyclic fatty acid - Maleimide - Carboxylic acid imide, n-substituted - Carboxylic acid imide - Dicarboximide - Pyrroline - Carboxylic acid derivative - Carboxylic acid - Monocarboxylic acid or derivatives - Azacycle - Organoheterocyclic compound - Organic oxide - Organic oxygen compound - Hydrocarbon derivative - Organonitrogen compound - Organooxygen compound - Organic nitrogen compound - Carbonyl group - Aliphatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as heterocyclic fatty acids. These are fatty acids containing a heterocyclic attached to the acyl chain.
• 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 Methanol
• Sensitivity: moisture sensitive
• Melt Point(°C): 96 °C
• Molecular Weight: 183.160 g/mol
• XLogP3: 0.400
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 183.053 Da
• Monoisotopic Mass: 183.053 Da
• Topological Polar Surface Area: 74.700 Ų
• Heavy Atom Count: 13
• Formal Charge: 0
• Complexity: 264.000
• 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. Jiaqi Qiu, Siyuan Xiang, Miyao Sun, Mingqian Tan.  (2023)  Preparation of Polysaccharide–Protein Hydrogels with an Ultrafast Self-Healing Property as a Superior Oral Delivery System of Probiotics.  JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY,      [PMID:37978937] [10.1021/acs.jafc.3c05898]

2. Hailiang Chen, Chenyu Liu, Simiao Yu, Hengjun Zhou, Farishta Shafiq, Weihong Qiao.  (2023)  αvβ3 Receptor-targeted acid-responsive controlled-release endosome escape doxorubicin-loaded liposomes for A549/ADR treatment.  COLLOIDS AND SURFACES A-PHYSICOCHEMICAL AND ENGINEERING ASPECTS,      [PMID:] [10.1016/j.colsurfa.2023.131990]

3. Pengxu Kong, Jing Dong, Wenchao Li, Zefu Li, Rui Gao, Xiang Liu, Jingrong Wang, Qi Su, Bin Wen, Wenbin Ouyang, Shouzheng Wang, Fengwen Zhang, Shuyi Feng, Donglin Zhuang, Yongquan Xie, Guangzhi Zhao, Hang Yi, Zujian Feng, Weiwei Wang, Xiangbin Pan.  (2023)  Extracellular Matrix/Glycopeptide Hybrid Hydrogel as an Immunomodulatory Niche for Endogenous Cardiac Repair after Myocardial Infarction.  Advanced Science,      [PMID:37318159] [10.1002/advs.202301244]

4. Hailiang Chen, Chenyu Liu, Simiao Yu, Hengjun Zhou, Farishta Shafiq, Weihong Qiao.  (2023)  Acid/GSH Dual-Responsive Endosome Escape Dual Pro-drug Micelles Targeted Synergistic Treatment for A549/ADR.  LANGMUIR,      [PMID:37219917] [10.1021/acs.langmuir.3c00439]

5. Xuedi Zhang, Xue Zhao, Zheng Hua, Shanghua Xing, Jiaxuan Li, Siyuan Fei, Mingqian Tan.  (2022)  ROS-triggered self-disintegrating and pH-responsive astaxanthin nanoparticles for regulating the intestinal barrier and colitis.  BIOMATERIALS,      [PMID:36495803] [10.1016/j.biomaterials.2022.121937]

6. Luo Zhenyu, Luo Lihua, Lu Yichao, Zhu Chunqi, Qin Bing, Jiang Mengshi, Li Xiang, Shi Yingying, Zhang Junlei, Liu Yu, Shan Xinyu, Yin Hang, Guan Guannan, Du Yongzhong, Cheng Ningtao, You Jian.  (2022)  Dual-binding nanoparticles improve the killing effect of T cells on solid tumor.  JOURNAL OF NANOBIOTECHNOLOGY,  20  (1): (1-13).  [PMID:35672752] [10.1186/s12951-022-01480-z]

7. Wen Liu, Jian Dai, Wei Xue.  (2018)  Design and self-assembly of albumin nanoclusters as a dynamic-covalent targeting co-delivery and stimuli-responsive controlled release platform.  Journal of Materials Chemistry B,  6  (42): (6817-6830).  [PMID:32254698] [10.1039/C8TB01791C]

8. Ling Wang, Jie Li, Danya Zhang, Songwei Tan, Guiying Jiang, Xueqian Wang, Fei Li, Ying Zhou, Pingbo Chen, Rui Wei, Ling Xi.  (2025)  TMTP1-Modified Polymeric Micelles for the Inhibition of Ovarian Cancer Metastasis and Recurrence through Enhanced Photothermal-Immunotherapy.  Materials Today Bio,      [PMID:40487160] [10.1016/j.mtbio.2025.101825]

9. Na Li, Ying Wang, Ling Yuan, Shuang Peng, Zhansheng Hu, Baoquan Wang, Dan Zhang, Longxiang Su, Huiping Wu.  (2025)  Mitochondrial energy reprogramming via dECM/GP@EVs@Gpnmb to prevent post-myocardial infarction heart failure.  CHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.cej.2025.165274]

10. Sanjiang Du, Hanlin Wang, Feiyang Geng, Zongxu Zhang, Chenghao Liu, Weiyue Lu, Gang Wei.  (2025)  Skin-penetrating peptides derived from computational simulation improve transdermal absorption and facilitate topical treatment of melanoma.  Acta Pharmaceutica Sinica B,      [PMID:41685147] [10.1016/j.apsb.2025.12.026]