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257370

Sigma-Aldrich

7-Amino-4-methylcoumarin

99%

Synonym(s):

Coumarin 120

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About This Item

Empirical Formula (Hill Notation):
C10H9NO2
CAS Number:
26093-31-2
Molecular Weight:
175.18
Beilstein:
142231
EC Number:
247-454-8
MDL number:
MFCD00006868
UNSPSC Code:
12352103
PubChem Substance ID:
57648146
NACRES:
NA.23

description

chromophore for enzyme substrates

Assay

99%

form

solid

mp

223-226 °C (lit.)

λmax

354 nm in ethanol

storage temp.

2-8°C

SMILES string

CC1=CC(=O)Oc2cc(N)ccc12

InChI

1S/C10H9NO2/c1-6-4-10(12)13-9-5-7(11)2-3-8(6)9/h2-5H,11H2,1H3

InChI key

GLNDAGDHSLMOKX-UHFFFAOYSA-N

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General description

7-Amino-4-methylcoumarin (coumarin120) is an aminocoumarin laser dye that can emit laser in the range of 370-760 nm. It has three intermolecular hydrogen bonded structures with C-H···O and N-H····O.

Application

Coumarin 120 is used as a fluorescent labeling reagent for trace determination of enzymes. It may be used as an antibacterial agent against MDR isolates of M. tuberculosis as it impacts the cell morphology. Coumarin 120 may also be used as an electron donor (amino groups) to transfer charge in a fluorescent sensor for the detection of mercury ions in aqueous media.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Fluorescence quenching of 7-amino-4-methylcoumarin by different TEMPO derivatives.
Zamojc K, et al.
Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy, 136(12), 1875-1880 (2015)
7-Amino-4-methylcoumarin.
Jasinski J and Woudenberg R
Acta Crystallographica Section C, Crystal Structure Communications, 50(12), 1954-1956 (1994)
A ?turn-on? coumarin-based fluorescent sensor with high selectivity for mercury ions in aqueous media.
Voutsadaki S, et al.
Chemical Communications (Cambridge, England), 46(19), 3292-3294 (2010)
Aldrichimica Acta, 15, 42-42 (1982)
Sander S van Berkel et al.
ChemMedChem, 7(4), 606-617 (2012-02-02)
The synthesis of a series of peptides containing C-terminal 7-amino-4-methylcoumarin (AMC) for use in the thrombin generation test (TGT) is described. The lead structure in this project was H-Gly-Gly-Arg-AMC, of which the water solubility and kinetic parameters (K(M) and k(cat))
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