6-Maleimidohexanoic acid N-hydroxysuccinimide este (EMCS) - ≥98% , CAS No.55750-63-5

CAS: 55750-63-5 Cat. No.: M122240 Molecular Weight: 308.29 Beilstein Registry Number: 1499815 EC Number: 637-238-5

GRADE & PURITY ≥98%

Synonyms

EMCS | Nmicos | Maleimide-(CH2)5-COONHS | GS-6679 | PD012171 | N-Succinimidyl 6-maleimidocaproate | AC-25054 | 1H-Pyrrole-2,5-dione, 1-(6-((2,5-dioxo-1-pyrrolidinyl)oxy)-6-oxohexyl)- | SY031503 | N-Succinimidyl 6-Maleimidohexanoate | 2,5-dioxopyrrolidin-1

Storage

Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

Application

Antibody Drug Conjugates(ADC), Drug Delivery, Surface Modification, PEGylation of Protein, Peptide & Oligo

Overview

A heterobifunctional cross-linking reagent incorporating an extended spacer with amine and sulfhydryl reactivity. Typically, coupled initially to molecules containing primary amines by amide bonds buffered at pH 7.5 (6.5-8.5) The second coupling is specific for molecules containing free sulfhydryl by thioether linkage buffered at pH 6.8 (6.5-7.0). Useful for preparation of enzyme immunoconjμgates and hapten carrier molecule conjμgates. Contains 9 atom linker. An extended aliphatic spacer stabilizes the maleimide prior to coupling compared to aromatic spacers.

Specifications

Synonyms

EMCS | Nmicos | Maleimide-(CH2)5-COONHS | GS-6679 | PD012171 | N-Succinimidyl 6-maleimidocaproate | AC-25054 | 1H-Pyrrole-2, 5-dione, 1-(6-((2, 5-dioxo-1-pyrrolidinyl)oxy)-6-oxohexyl)- | SY031503 | N-Succinimidyl 6-Maleimidohexanoate | 2, 5-dioxopyrrolidin-1

Specifications & Purity

≥98%

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%

Names and Identifiers

• Canonical Smiles: C1CC(=O)N(C1=O)OC(=O)CCCCCN2C(=O)C=CC2=O
• IUPAC Name: (2,5-dioxopyrrolidin-1-yl) 6-(2,5-dioxopyrrol-1-yl)hexanoate
• InChIKey: VLARLSIGSPVYHX-UHFFFAOYSA-N
• INCHI: 1S/C14H16N2O6/c17-10-5-6-11(18)15(10)9-3-1-2-4-14(21)22-16-12(19)7-8-13(16)20/h5-6H,1-4,7-9H2
• Isomeric SMILES: C1CC(=O)N(C1=O)OC(=O)CCCCCN2C(=O)C=CC2=O
• WGK Germany: 3
• Molecular Weight: 308.29
• Beilstein: 1499815
• Reaxy-Rn: 1499815
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1499815&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: Maleimides
• Alternative Parents: Pyrrolidine-2-ones N-substituted carboxylic acid imides Pyrrolines Dicarboximides Lactams Monocarboxylic acids and derivatives Azacyclic compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic heteromonocyclic compounds
• Substituents: Maleimide - Carboxylic acid imide, n-substituted - 2-pyrrolidone - Carboxylic acid imide - Dicarboximide - Pyrroline - Lactam - Carboxylic acid derivative - Monocarboxylic acid or derivatives - Azacycle - Hydrocarbon derivative - Carbonyl group - Organic oxide - Organic oxygen compound - Organic nitrogen compound - Organonitrogen compound - Organooxygen compound - Aliphatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as maleimides. These are compounds containing a 2,5-pyrroledione moiety.
• 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

• Sensitivity: light & Moisture & heat sensitive
• Melt Point(°C): 71°C
• Molecular Weight: 308.290 g/mol
• XLogP3: -0.500
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 8
• Exact Mass: 308.101 Da
• Monoisotopic Mass: 308.101 Da
• Topological Polar Surface Area: 101.000 Ų
• Heavy Atom Count: 22
• Formal Charge: 0
• Complexity: 520.000
• 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. Chao Zhang, HongLei Zhang, MengNan Han, XueLi Yang, ChaoHong Pei, ZhiDong Xu, Jie Du, Wei Li, Shengxi Chen.  (2019)  DNA–affibody nanoparticle delivery system for cisplatin-based breast cancer chemotherapy.  RSC Advances,  9  (4): (1982-1989).  [PMID:35516156] [10.1039/C8RA08735K]

2. Fengyin Liu, Zijian Chen, Yudong Shen, Yuanming Sun, Jinyi Yang, Hong Wang, Hongtao Lei, Zhenlin Xu.  (2018)  Hapten synthesis and production of specific antibody against 3-amino-5-morpholinomethyl-2-oxazolidone for immunoassay without derivatisation.  FOOD AND AGRICULTURAL IMMUNOLOGY,      [PMID:] [10.1080/09540105.2017.1376038]

3. Na Zhao, Baoyan Wu, Xianglong Hu, Da Xing.  (2017)  NIR-triggered high-efficient photodynamic and chemo-cascade therapy using caspase-3 responsive functionalized upconversion nanoparticles.  BIOMATERIALS,      [PMID:28666101] [10.1016/j.biomaterials.2017.06.031]

4. Dong Wei, Wang Guihu, Chai Yichao, Li Wenjuan, Liu Shichang, Liu Huasheng, Guo Wenlei, Li Senyang, He Xinrui, Wan Mingxi, Li Zongfang, Zong Yujin.  (2025)  Two-step ultrasonic cavitation controlled delivery of brain exogenous nucleic acids for ischemic stroke using acoustic-cationic-polymeric-nanodroplets.  Drug Delivery and Translational Research,      [PMID:40048146] [10.1007/s13346-025-01828-6]