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Key Documents

A9891

Sigma-Aldrich

7-Amino-4-methylcoumarin

chromophore for enzyme substrates, fluorogenic, ≥98% (HPLC), powder

Sinônimo(s):

Coumarin 120

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About This Item

Fórmula empírica (Notação de Hill):
C10H9NO2
Número CAS:
Peso molecular:
175.18
Beilstein:
142231
Número CE:
Número MDL:
Código UNSPSC:
12352204
ID de substância PubChem:
NACRES:
NA.32

product name

7-Amino-4-methylcoumarin, Chromophore for substrates

Nível de qualidade

descrição

chromophore for enzyme substrates

Ensaio

≥98% (HPLC)

forma

powder

pf

223-226 °C (lit.)

solubilidade

acetone: 10 mg/mL, clear, colorless to yellow

fluorescência

λex 365 nm; λem 440 nm in ethanol(lit.)

temperatura de armazenamento

2-8°C

cadeia de caracteres SMILES

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

chave InChI

GLNDAGDHSLMOKX-UHFFFAOYSA-N

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Aplicação

7-Amino-4-methylcoumarin has been used:
  • to determine cathepsin B like- activity
  • as a substrate for leucine aminopeptidase (LAP)
  • in chymotryptic assay
  • as a standard to detect the activation of caspase-3 during
  • sanguinarine-induced damage
  • protection by human DEAD-box DDX3

Used as matrix for analysis of monosulfated disaccharides and as a co-matrix with 6-aza-2-thiothymidine for sulfated neutral and sialylated tri-and tetrasaccharides.

Ações bioquímicas/fisiológicas

7-Amino-4-methylcoumarin is a coumarin derivative, which serves as a fluorescence reference standard to screen protease inhibitors.

Nota de preparo

Soluble in DMSO (10 mg/mL), DMF, and acetone (10 mg/mL).

Outras notas

Reagent for preparing new fluorogenic AMC-based substrates for cystine aminopeptidase (and other hydrolases); used as reference compound in the enzyme assay.

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

dust mask type N95 (US), Eyeshields, Gloves


Certificados de análise (COA)

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Issues in Chemistry and General Chemical Research (2012)
Significant activities of extracellular enzymes from a brown tide in the coastal waters of Qinhuangdao, China
Ou L, et al.
Harmful Algae, 74, 1-9 (2018)
Regulation of p21 expression for anti-apoptotic activity of DDX3 against sanguinarine-induced cell death on intrinsic pathway
Nguyen CN, et al.
Phytomedicine, 153096-153096 (2019)
Berberine-induced cardioprotection and Sirt3 modulation in doxorubicin-treated H9c2 cardiomyoblasts
Coelho AR, et al.
Biochimica et Biophysica Acta (BBA)-Molecular Basis of Disease, 1863(11), 2904-2923 (2017)
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))

Artigos

Glycosylation is known to have profound influence on various physiochemical, cellular and biological functions of proteins. Alterations in this modification are known to affect the immune system and have been associated with various pathological states such as cancer, rheumatoid arthritis, and inflammatory diseases.

Glycosylation is known to have profound influence on various physiochemical, cellular and biological functions of proteins. Alterations in this modification are known to affect the immune system and have been associated with various pathological states such as cancer, rheumatoid arthritis, and inflammatory diseases.

Mass Spectrometry of Glycans, method comparison and products

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