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A9891

Sigma-Aldrich

7-Amino-4-methylcoumarin

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

Synonym(s):

Coumarin 120

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250 MG
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250 MG
CN¥1,057.45
500 MG
CN¥2,776.18
1 G
CN¥3,865.78

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:
12352204
PubChem Substance ID:
24891406
NACRES:
NA.32

CN¥1,057.45

List priceCN¥1,244.06Save 15%

Available to ship onApril 07, 2025Details

New, lower price on this item!

Product Name

7-Amino-4-methylcoumarin, Chromophore for substrates

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

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1 of 4

This Item
A3401257370M5639
7-Amino-4-methylcoumarin Chromophore for substrates

A9891

7-Amino-4-methylcoumarin

Ala-Ala-Phe-7-amido-4-methylcoumarin protease substrate

A3401

Ala-Ala-Phe-7-amido-4-methylcoumarin

7-Amino-4-methylcoumarin 99%

257370

7-Amino-4-methylcoumarin

4-Methylumbelliferyl β-D-N,N′,N′′-triacetylchitotrioside fluorogenic glycanase substrate

M5639

4-Methylumbelliferyl β-D-N,N′,N′′-triacetylchitotrioside

solubility

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

solubility

ethanol: 20 mg/mL, clear, colorless to light yellow

solubility

-

solubility

water: pyridine, 1:1: 4.90-5.10 mg/mL, clear, colorless to light yellow

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

300

form

powder

form

powder

form

solid

form

powder

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

fluorescence

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

fluorescence

-

fluorescence

-

fluorescence

-

Application

7-Amino-4-methylcoumarin has been used:
  • to determine cathepsin B like- activity[1]
  • as a substrate for leucine aminopeptidase (LAP)[2]
  • in chymotryptic assay[3]
  • as a standard to detect the activation of caspase-3 during
  • sanguinarine-induced damage
  • protection by human DEAD-box DDX3[4]

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.[5]

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.

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
  • Specification Sheet

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    Certificates of Analysis (COA)

    Lot/Batch Number
    0000429351
    0000429351
    0000414879
    0000414879
    0000394185

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    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)
    Issues in Chemistry and General Chemical Research (2012)
    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)
    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))
    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)
    View All Related Papers

    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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