7-Amino-4-methyl-3-coumarinylacetic acid(AMCA) - for fluorescence analysis, Ex:387nm, Em:470nm, ≥90%(HPLC) , CAS No.106562-32-7

CAS: 106562-32-7 Cat. No.: A131039 Molecular Weight: 233.22 Beilstein Registry Number: 7927205 EC Number: 635-163-2

GRADE & PURITY for Fluorescence analysis, Ex:387nm, Em:470nm, ≥90%(HPLC)

Synonyms

AMCA-H | 7-Amino-4-methylcoumarin-3-acetate | 7-Amino-4-methylcoumarin-3-acetic acid | 2-(7-amino-4-methyl-2-oxochromen-3-yl)acetic acid | A801463 | 2H-1-Benzopyran-3-acetic acid | SCHEMBL72225 | ?AMCA | J-100002 | 7-Amino-4-methyl-3-coumarinylacetic acid

Storage

Room temperature

Shipped In

Normal

Overview

Non-activated, Amine-reactive, fluorescent probe that can be conjugated to biomolecules.
A blue fluorophore useful for immunofluorescence and peptide labeling.AMCA is a useful agent for labeling proteins. Demonstrates a characteristic absorption peak at 345 nm with a fluorescence emission at 440-460 nm (blue region); however, when conjugated with proteins the absorption peak shifts to 355 nm with a fluorescence emission at 440-460 nm. It has a high fluorescence yield with a sufficient Stokes shift (100 nm) and is relatively photostable.Relatively easy to activate and couple to the N-terminal amino group of a peptide resulting in an acid stable amide bond.

Fluorescence: λex 350 nm，λem 433 nm in methanol

Specifications

Synonyms

AMCA-H | 7-Amino-4-methylcoumarin-3-acetate | 7-Amino-4-methylcoumarin-3-acetic acid | 2-(7-amino-4-methyl-2-oxochromen-3-yl)acetic acid | A801463 | 2H-1-Benzopyran-3-acetic acid | SCHEMBL72225 | ?AMCA | J-100002 | 7-Amino-4-methyl-3-coumarinylacetic acid

Specifications & Purity

for fluorescence analysis, Ex:387nm, Em:470nm, ≥90%(HPLC)

Storage

Room temperature

Shipped In

Normal

Grade

Em:470nm, Ex:387nm, for Fluorescence analysis

Purity

≥90%(HPLC)

Names and Identifiers

• Canonical Smiles: CC1=C(C(=O)OC2=C1C=CC(=C2)N)CC(=O)O
• IUPAC Name: 2-(7-amino-4-methyl-2-oxochromen-3-yl)acetic acid
• InChIKey: QEQDLKUMPUDNPG-UHFFFAOYSA-N
• INCHI: 1S/C12H11NO4/c1-6-8-3-2-7(13)4-10(8)17-12(16)9(6)5-11(14)15/h2-4H,5,13H2,1H3,(H,14,15)
• Isomeric SMILES: CC1=C(C(=O)OC2=C1C=CC(=C2)N)CC(=O)O
• WGK Germany: 3
• Molecular Weight: 233.22
• Beilstein: 7927205
• Reaxy-Rn: 7927205
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=7927205&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Class Coumarins and derivatives

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Class: Coumarins and derivatives
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Coumarins and derivatives
• Alternative Parents: 1-benzopyrans Pyranones and derivatives Benzenoids Heteroaromatic compounds Lactones Amino acids Oxacyclic compounds Monocarboxylic acids and derivatives Carboxylic acids Primary amines Organopnictogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Coumarin - Benzopyran - 1-benzopyran - Pyranone - Pyran - Benzenoid - Heteroaromatic compound - Amino acid or derivatives - Amino acid - Lactone - Oxacycle - Organoheterocyclic compound - Carboxylic acid derivative - Carboxylic acid - Monocarboxylic acid or derivatives - Amine - Organonitrogen compound - Organooxygen compound - Primary amine - Organic oxygen compound - Organopnictogen compound - Organic oxide - Carbonyl group - Organic nitrogen compound - Hydrocarbon derivative - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one).
• 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 DMF, DMSO, aqueous base, 10% NaOH solution (freely soluble) at 20 °C, alcohol at 20 °C, acetone at 20 °C, and ether (slightly soluble) at 20 °C. Insoluble in water.
• Sensitivity: Light & Moisture Sensitive
• Molecular Weight: 233.220 g/mol
• XLogP3: 0.600
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 233.069 Da
• Monoisotopic Mass: 233.069 Da
• Topological Polar Surface Area: 89.600 Ų
• Heavy Atom Count: 17
• Formal Charge: 0
• Complexity: 388.000
• 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. Ti Qin, Pinhao Li, Jun Li, Qianqian Guo, Ying Chen, Yu-E Wang, Ling Tao, Jian Huang, Xiangchun Shen, Xingjie Wu.  (2023)  Size-Exclusion Chromatography-Based Extracellular Vesicles Size Subtyping and Multiplex Membrane Protein Profiling for Differentiating Gastrointestinal Cancer Prognosis.  ANALYST,      [PMID:37842723] [10.1039/D3AN01027A]

2. Qiwei Liang, Xiancan Ban, Siyuan Jiang, Zhi Zeng, Huigang Feng, Yufeng Ye, Yi Zhang, Yan-Qing Guan, Yi Huang.  (2025)  Enhancing thrombolysis through targeted delivery of urokinase by H2O2-responsive nanoparticles delivery system.  COLLOIDS AND SURFACES B-BIOINTERFACES,      [PMID:40513212] [10.1016/j.colsurfb.2025.114849]

3. Chen Yue, Chen Qinyi, Ma Yuanyuan, Zhang Cheng, Xu Jie, Li Kejing, Sun Yajie, Su Xinge, Wei Mingguang, Bao Rui, Ding Tong, Tang Longguang, Yu Wenying, Ju Shenghong, Fan Wenpei.  (2026)  In situ self-assembled cell reservoir hydrogel for maneuvering multistage radioimmunotherapy.  Nature Communications,      [PMID:41565700] [10.1038/s41467-026-68490-5]