Name | 7-amino-4-(trifluoromethyl)-2-benzopyrone |
Synonyms | Coumarin 490 Coumarin 151 7-AMIDO-4-TRIFLUOROMETHYLCOUMARIN 7-Amino-4-(trifluoromethyl)coumarin 7-amino-4-(trifluoromethyl)-2-benzopyrone 7-AMINO-4-(TRIFLUOROMETHYL)COUMARIN, FOR FLUORESCENCE |
CAS | 53518-15-3 |
EINECS | 258-599-1 |
InChI | InChI=1/C10H6F3NO2/c11-10(12,13)7-4-9(15)16-8-3-5(14)1-2-6(7)8/h1-4H,14H2 |
Molecular Formula | C10H6F3NO2 |
Molar Mass | 229.16 |
Density | 1.4096 (estimate) |
Melting Point | 221-222℃ |
Boling Point | 314.6±42.0 °C(Predicted) |
Water Solubility | Soluble in dimethyl sulfoxide (25 mg/ml), dimethyl formamide (25 mg/ml), and methanol (25 mg/ml). Insoluble in water. |
Appearance | Form Powder, Color Yellow |
pKa | 1.12±0.20(Predicted) |
Storage Condition | under inert gas (nitrogen or Argon) at 2–8 °C |
MDL | MFCD00006858 |
Physical and Chemical Properties | EPA Chemical Information 2H-1-Benzopyran-2-one, 7-amino-4-(trifluoromethyl)- (53518-15-3) |
Use | Uses can be used as fluorescent labeling of laser dyes and proteases. |
Hazard Symbols | Xn - Harmful |
Risk Codes | R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. R36/37/38 - Irritating to eyes, respiratory system and skin. |
Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S37/39 - Wear suitable gloves and eye/face protection |
WGK Germany | 3 |
TSCA | T |
HS Code | 29322090 |
Hazard Class | IRRITANT |
biological activity
7-Amino-4-(trifluoromethyl)coumarin (Coumarin 151) is a fluorescent marker that can be used to sensitively detect proteases. Its excitation and emission wavelengths are 400 and 500 nm respectively.
in vitro studies
Amino acid and peptide derivatives of 7-amino-4-(trifluoromethyl)coumarin are used to monitor peptidase activities. Caspase activation is measured using the fluorogenic compound N-acetyl-asp-glu-val-asp-7-Amino-4-(trifluoromethyl)coumarin (Ac-DEVD-AFC). This substrate rapidly enters cells where it is efficiently cleaved at the aspartate residue by specific caspases, yielding the fluorescent compound 7-Amino-4-(trifluoromethyl)coumarin (AFC). Following cell disruption, released 7-Amino-4-(trifluoromethyl)coumarin is separated on HPLC and detected by fluorescence. The appearance of 7-Amino-4-(trifluoromethyl)coumarin in cells is blocked by the pancaspase inhibitor benzyloxycarbonyl-val-ala-asp-fluoromethylketone, thus establishing that intracellular caspases are responsible for the cleavage. γ-glutamyl-7-amino-4-(trifluoro-methyl)coumarin is synthesized and used as a substrate for fluirimetric assay of γ-gluta-myltranspeptidase. The reaction product 7-amino-4-(trifluoromethyl)coumarin is fluorescent at neutral pH values and with excitation and emission wavelengths of 400 and 490 nm, respectively, concentration is linearly related to fluorescence over the range of 10 to 300 pmol/3 mL reaction mixture.
Hazard Note | Irritant |
BRN | 4456797 |