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7-Amino-4-methylcoumarin Chromophore for substrates

Sigma-Aldrich

A9891

7-Amino-4-methylcoumarin

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

Sigma-Aldrich

A3401

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

Sigma-Aldrich

257370

7-Amino-4-methylcoumarin

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

Sigma-Aldrich

M5639

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

Chromophore for substrates

protease substrate

99%

fluorogenic glycanase substrate

A9891

7-Amino-4-methylcoumarin

A3401

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

257370

7-Amino-4-methylcoumarin

M5639

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

Description

Synonyms

Coumarin 120

H-Ala-Ala-Phe-AMC

Coumarin 120

4-Methyl-7-coumarinyl-tri-N-acetyl-β-chitotrioside, 4-Methylumbelliferyl-N,N′,N″-triacetyl-β-chitotrioside

CAS Number

Molecular Formula

Empirical Formula (Hill Notation)

: C₁₀H₉NO₂

Empirical Formula (Hill Notation)

: C₂₅H₂₈N₄O₅

Empirical Formula (Hill Notation)

: C₁₀H₉NO₂

Empirical Formula (Hill Notation)

: C₃₄H₄₇N₃O₁₈

Molecular Weight

: 175.18

Molecular Weight

: 464.51

Molecular Weight

: 175.18

Molecular Weight

: 785.75

MDL Number

MFCD00006868

MFCD00070149

MFCD00006868

MFCD00036892

Quality Designations

300

Properties

λ<SUB>max</SUB>:

354 nm in ethanol

λ<SUB>max</SUB>:

Assay:

≥98% (HPLC)

Assay:

≥98% (TLC)

Assay:

99%

Assay:

≥98.00% (TLC)

fluorescence:

λ_ex 365 nm; λ_em 440 nm in ethanol(lit.)

fluorescence:

description:

chromophore for enzyme substrates

description:

chromophore for enzyme substrates

description:

InChI:

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

InChI:

1S/C25H28N4O5/c1-14-11-22(30)34-21-13-18(9-10-19(14)21)28-25(33)20(12-17-7-5-4-6-8-17)29-24(32)16(3)27-23(31)15(2)26/h4-11,13,15-16,20H,12,26H2,1-3H3,(H,27,31)(H,28,33)(H,29,32)

InChI:

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

InChI:

1S/C34H47N3O18/c1-12-7-22(44)50-18-8-16(5-6-17(12)18)49-32-24(36-14(3)42)28(47)30(20(10-39)52-32)55-34-25(37-15(4)43)29(48)31(21(11-40)53-34)54-33-23(35-13(2)41)27(46)26(45)19(9-38)51-33/h5-8,19-21,23-34,38-40,45-48H,9-11H2,1-4H3,(H,35,41)(H,36,42)(H,37,43)/t19-,20-,21-,23-,24-,25-,26-,27-,28-,29-,30-,31-,32-,33+,34+/m1/s1

InChI key:

GLNDAGDHSLMOKX-UHFFFAOYSA-N

InChI key:

FVRLYIFIDKXFHU-UHFFFAOYSA-N

InChI key:

GLNDAGDHSLMOKX-UHFFFAOYSA-N

InChI key:

BNYGKUQXGBVTRE-JFWBNMEYSA-N

mp:

223-226 °C (lit.)

mp:

223-226 °C (lit.)

mp:

form:

powder

form:

powder

form:

solid

form:

powder

SMILES string:

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

SMILES string:

CC(N)C(=O)NC(C)C(=O)NC(Cc1ccccc1)C(=O)Nc2ccc3C(C)=CC(=O)Oc3c2

SMILES string:

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

SMILES string:

CC(=O)N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@H]2[C@H](O)[C@@H](NC(C)=O)[C@@H](O[C@@H]2CO)O[C@H]3[C@H](O)[C@@H](NC(C)=O)[C@@H](O[C@@H]3CO)Oc4ccc5C(C)=CC(=O)Oc5c4

solubility:

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

solubility:

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

solubility:

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

storage temp.:

2-8°C

storage temp.:

2-8°C

storage temp.:

2-8°C

storage temp.:

2-8°C

Quality Level:

300

Usage and Safety

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.

Ala-Ala-Phe-7-amido-4-methylcoumarin has been used:

in the preparation of the reaction mixture for enzymatic assays
to initiate the enzyme reaction in tripeptidyl peptidase-1 (TPP1) enzyme activity assay
to initiate the assay reaction in lysosomal hydrolases activity assay

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.

4-Methylumbelliferyl β-D-N,N′,N′′-triacetylchitotrioside has been used as a fluorogenic substrate to determine chitinase and chitotriosidase enzyme activity.

Risk and Safety

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

Storage Class Code:

11 - Combustible Solids

WGK:

WGK 3

Flash Point(F):

Not applicable

Flash Point(C):

Not applicable

Personal Protective Equipment:

Eyeshields, Gloves, type N95 (US)

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

Storage Class Code:

11 - Combustible Solids

WGK:

WGK 3

Flash Point(F):

Not applicable

Flash Point(C):

Not applicable

Personal Protective Equipment:

Eyeshields, Gloves, type N95 (US)