7-Amino-4-methylcoumarin (CAS 26093-31-2)

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Synonym:	Coumarin 120; AMC
Application:	A fluorogenic reagent and antibacterial, antifungal agent
CAS Number:	26093-31-2
Purity:	≥98%
Molecular Weight:	175.2
Molecular Formula:	C₁₀H₉NO₂

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Description

7-Amino-4-methylcoumarin (AMC) is a well-known laboratory reagent employed in the preparation of fluorogenic AMC-based substrates for the detection of proteolytic enzyme activity. AMC has been utilized as a fluorescent probe to analyze glycoproteins' monosaccharides and N-linked oligosaccharides via chromatography and has been used as a laser dye. Recent research shows that AMC was extracted from an endophytic Xylaria fungal species and exhibited strong antibacterial and antifungal activities in vitro against Aspergillus, Candida, Escherichia, Staphylococcus, Salmonella and Vibrio species, among others. This product is also useful as a reference standard in enzymatic assays.

Technical Information

Appearance:	Yellow
Physical State:	Solid
Solubility:	Soluble in acetone (10 mg/ml), DMSO (10 mg/ml), and DMF.
Storage:	Store at 4° C
Melting Point:	223-226 °C (lit.)
Boiling Point:	378.26 °C at 760 mmHg (Predicted)
Density:	1.28 g/cm³ (Predicted)
Refractive Index:	n²⁰_D 1.63 (Predicted)
Fluoresence:	λex 365 nm, λem 440 nm in ethanol; λex 428 nm, λem 441 nm in methanol; λex 380 nm, λem 460 nm
IC50:	HIV-1(RF) : IC₅₀ = 5.21 µM (CEM); HIV-1(RF) : EC₅₀50 = >149 µM (CEM)
Ki Data:	Carbonic anhydrase XII: K_i= 9.13 µM (human); Carbonic anhydrase IX: K_i= 7.64 µM (human); Carbonic anhydrase I: K_i= 5.56 µM (human)

Safety and Reference Information

Transport:	UN 2811, Class 6.1, Packing group III
WGK Germany:	3
PubChem CID:	92249
MDL Number:	MFCD00006868
EC Number:	247-454-8
Beilstein Registry:	142231
SMILES:	CC1=CC(=O)OC2=C1C=CC(N)=C2

For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.

References

1. Zimmerman, M., et al. 1977. Anal. Biochem. 78: 47-51. PMID: 848756
2. Kanaoka, Y., et al. 1982. Chem. Pharm. Bull. 30: 1485-1487. PMID: 7105264
3. Liu, X et al. 2008. Appl. Microbiol. Biotechnol. 78: 241-247. PMID: 18092158
4. Yodoshi, M., et al. 2008. J Chromatogr A. 1203: 137-145. PMID: 18684461

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Datasheet/SDS