7-Amino-4-methylcoumarin [26093-31-2] – general description and application

General description of 7-Amino-4-methylcoumarin:

7-Amino-4-methylcoumarin [26093-31-2] (AMC), also known as Coumarin 120 belongs to the family of benzo-α-pyrones, called coumarins. It is a yellow crystalline solid with the melting point of 222-223 °C. It is soluble in common organic solvents.[1] 7-amino-4-methylcoumarin laser dye can emit laser in the range of 370-760 nm with the maximum λ at 354 nm (in ethanol). This compound is sensitive to the light and oxidizing agents therefore should be store in a dark, dry, tightly closed container.

The most common method of preparation was published by Pechmann and Schwarz in 1899. It is based on the condensation of m-aminophenol with acetoacetic ester by heating in an alcohol in the presence of zinc chloride. Using this procedure, the AMC can be obtained in one step.[2]

Application of 7-Amino-4-methylcoumarin:

Coumarin 120 is widely used as commercially available building block in the synthesis of fluorescent probes for a variety of sensing experiments in the enzymology. Such π-π conjugated system with electron-rich and charge transfer properties leads to the applications as fluorescent sensors for biological activities. Traditionally, coumarin substrates have been used to measure oxidative activities of cytochrome P450 (CYP) enzymes.[3] Moreover, it is widely used for peptide labeling in the study of proteases.[4] Coumarin-based chemosenors are used in selective detection of trace metals.[5] 7-Amino-4-methylcoumarin shows potential as antitubercular agent (the lowest MIC of 1 mg/L) by cell-wall-attacking mechanism of action.[6]

Product categorization (Chemical groups):

Main category:

Second level:

Third level:


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[2] H. Pechmann, O. Schwarz, Ber. Dtsch. Chem. Ges. 1899, 32, 3696.
[3] D. Kim, Z. Wu, F. P. Guengerich J. Cell Biol. 2005, 280, 40319.
A. F. Kisselev, A. L. Goldberg Meth. Enzymol. 2005, 398, 364.
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[6] R. Tandon, P. Ponnan, N. Aggarwal, R. Pathak, A. S. Baghel, G. Gupta, A. Arya, M. Nath, V. S. Parmar, H. G. Raj, A. K. Prasad, M. Bose, J. Antimicrob. Chemother. 2011, 66, 2543.