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A9891

Sigma-Aldrich

7-Amino-4-methylcoumarin

Chromophore for substrates

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Synonym(s):
Coumarin 120
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:
12352204
PubChem Substance ID:
24891406
NACRES:
NA.32

Quality Level

200

description

chromophore for enzyme substrates

Assay

≥98% (HPLC)

form

powder

mp

223-226 °C (lit.)

solubility

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

fluorescence

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

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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Application

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.

Biochem/physiol Actions

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

Preparation Note

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

Other Notes

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

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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Articles

Enzymatic Assay of Cathepsin B

Cathepsin B is a lysosomal cysteine proteinase with broad specificity. This protocol uses Nα–CBZ–Arg–Arg–7–amido–4–methylcoumarin as the substrate for fluorometric detection of Cathepsin B activity.

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