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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:
Molecular Weight:
175.18
Beilstein:
142231
EC Number:
MDL number:
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.23

description

chromophore for enzyme substrates

Quality Level

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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Aldrichimica Acta, 15, 42-42 (1982)
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)
Bernadette S Creaven et al.
Journal of inorganic biochemistry, 103(9), 1196-1203 (2009-07-28)
The condensation of 7-amino-4-methyl-coumarin (1) with a number of substituted salicylaldehydes yielded a series of Schiff bases (2a-2k) in good yields. Subsequent reaction of these ligands with copper(II) acetate yielded Cu(II) complexes (3a-3k) and some were characterised using X-ray crystallography.
Letícia Christina Pires Gonçalves et al.
PloS one, 8(1), e53874-e53874 (2013-01-24)
A model betalainic dye was semisynthesized from betanin, the magenta pigment of the red beet, and was effective for live-cell imaging of Plasmodium-infected red blood cells. This water-soluble fluorescent probe is photostable, excitable in the visible region and cell membrane-permeable

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