November 08, 20217-Amino-4-methylcoumarin [26093-31-2] – general description and application
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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:
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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.
[4]
A. F. Kisselev, A. L. Goldberg Meth. Enzymol. 2005, 398, 364.
Kanaoka, T. Takahashi, H. Nakayama, T. Ueno, T. Sekine Chem. Pharm. Bull. 1982, 30, 1485.
Ishida, Y. Nakamura, T. Ohta, Y. Oe Molecules 2021, 26, 482.
[5]
L. Huang, W. Sheng, L. Wang, X. Meng, H. Duan, L. Chi RSC Adv, 2021, 11, 23597.
Muthusamy, K. Rajalakshmi, D. Zhu, W. Zhu, S. Wang, K. Lee, H. Xu, L. Zhao Sens. Actuators B Chem. 2021, 346, 130534.
[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.