Fluorescein-5-maleimide - ≥97%(HPLC) , CAS No.75350-46-8

CAS: 75350-46-8 Cat. No.: M131300 Molecular Weight: 427.363 EC Number: 635-131-8

GRADE & PURITY ≥97%(HPLC)

Synonyms

5-MF | SCHEMBL454005 | W-100077 | C24H13NO7 | D90687 | Fluorescein-5-maleimide (contains 2% N,N-Dimethylformamide at maximum) | 5-Maleimidofluorescein | AKOS016008608 | A923201 | FT-0626456 | 5-MF | 1H-Pyrrole-2,5-dione, 1-(3',6'-dihydroxy-3-oxospiro(isob

Storage

Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

Overview

Fluorescein 5-Maleimide is a protein and peptide fluorescent labeling reagent. 5-MF is a thiol-reactive Fluorescent Probe for bioconjugation.
It is used to fluorescence label molecules such as proteins and peptides via their thiol groups.

Specifications

Synonyms

5-MF | SCHEMBL454005 | W-100077 | C24H13NO7 | D90687 | Fluorescein-5-maleimide (contains 2% N, N-Dimethylformamide at maximum) | 5-Maleimidofluorescein | AKOS016008608 | A923201 | FT-0626456 | 5-MF | 1H-Pyrrole-2, 5-dione, 1-(3', 6'-dihydroxy-3-oxospiro(isob

Specifications & Purity

≥97%(HPLC)

Biochemical and Physiological Mechanisms

Fluorescein-5-maleimide is a fluorescent thiol-reactive dye used to conjugate fluorescein to proteins (excitation: 494 nm, emission: 519 nm).

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

≥97%(HPLC)

Names and Identifiers

• Canonical Smiles: C1=CC2=C(C=C1N3C(=O)C=CC3=O)C(=O)OC24C5=C(C=C(C=C5)O)OC6=C4C=CC(=C6)O
• IUPAC Name: 1-(3',6'-dihydroxy-3-oxospiro[2-benzofuran-1,9'-xanthene]-5-yl)pyrrole-2,5-dione
• InChIKey: AYDAHOIUHVUJHQ-UHFFFAOYSA-N
• INCHI: 1S/C24H13NO7/c26-13-2-5-17-19(10-13)31-20-11-14(27)3-6-18(20)24(17)16-4-1-12(9-15(16)23(30)32-24)25-21(28)7-8-22(25)29/h1-11,26-27H
• Isomeric SMILES: C1=CC2=C(C=C1N3C(=O)C=CC3=O)C(=O)OC24C5=C(C=C(C=C5)O)OC6=C4C=CC(=C6)O
• WGK Germany: 3
• Molecular Weight: 427.363
• Reaxy-Rn: 7953995
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=7953995&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Benzopyrans
      • Subclass 1-benzopyrans
        • Level5 Dibenzopyrans
          • Level6 Xanthenes

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Benzopyrans
• Subclass: 1-benzopyrans
• Intermediate Tree Nodes: Dibenzopyrans
• Direct Parent: Xanthenes
• Alternative Parents: Diarylethers Phthalides Benzofuranones Isobenzofurans 1-hydroxy-2-unsubstituted benzenoids Maleimides N-substituted carboxylic acid imides Pyrrolines Dicarboximides Carboxylic acid esters Lactones Oxacyclic compounds Monocarboxylic acids and derivatives Azacyclic compounds Hydrocarbon derivatives Organic oxides Organonitrogen compounds Carbonyl compounds Organopnictogen compounds
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Xanthene - Diaryl ether - Benzofuranone - Phthalide - Isobenzofuranone - Isocoumaran - Isobenzofuran - 1-hydroxy-2-unsubstituted benzenoid - Maleimide - Carboxylic acid imide, n-substituted - Benzenoid - Carboxylic acid imide - Dicarboximide - Pyrroline - Lactone - Carboxylic acid ester - Monocarboxylic acid or derivatives - Ether - Carboxylic acid derivative - Oxacycle - Azacycle - Carbonyl group - Organic oxide - Organooxygen compound - Organonitrogen compound - Organopnictogen compound - Organic nitrogen compound - Organic oxygen compound - Hydrocarbon derivative - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as xanthenes. These are polycyclic aromatic compounds containing a xanthene moiety, which consists of two benzene rings joined to each other by a pyran 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

Mechanisms of Action

Chemical and Physical Properties

• Sensitivity: Heat & Light & Moisture & Air-sensitive
• Molecular Weight: 427.400 g/mol
• XLogP3: 2.500
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 1
• Exact Mass: 427.069 Da
• Monoisotopic Mass: 427.069 Da
• Topological Polar Surface Area: 113.000 Ų
• Heavy Atom Count: 32
• Formal Charge: 0
• Complexity: 826.000
• 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. Yingjie Zhang, Changfei Duan, Qing Li, Yuchen Bai, Baolei Dong, Yingying Tang, Min He, Chenqi Hao, Kai Wen, Jianzhong Shen, Zhanhui Wang.  (2022)  Fluorescence polarization immunoassay based on fragmentary hapten for rapid and sensitive screening of polymyxins in human serum.  SENSORS AND ACTUATORS B-CHEMICAL,      [PMID:] [10.1016/j.snb.2022.132404]

2. Huixia Di, Erzao Zeng, Pengjuan Zhang, Xuehui Liu, Cai Zhang, Jie Yang, Dingbin Liu.  (2019)  General Approach to Engineering Extracellular Vesicles for Biomedical Analysis.  ANALYTICAL CHEMISTRY,      [PMID:31529961] [10.1021/acs.analchem.9b02268]

3. Zhijiao Huang, Yong Liu, Lungang Chen, Xinghua Zhang, Jianguo Liu, Chenguang Wang, Qi Zhang, Longlong Ma.  (2024)  Selective hydrodeoxygenation of 5-hydromethylfurfural to 2,5-dimethylfuran over PtFe/C catalyst.  Molecular Catalysis,      [PMID:] [10.1016/j.mcat.2024.114169]