coumarin 151

Names

[ Name ]:
coumarin 151

[Synonym ]:
7-Amino-4-(trifluoromethyl)-2H-chromen-2-one
2H-1-Benzopyran-2-one, 7-amino-4- (trifluoromethyl)-
7-amino-4-trifluoromethylchromen-2-one
MFCD00006858
Coumarin 151
7-NH2-4-CF3-coumarin
7-Amino-4-(trifluoromethyl)coumarin
7-amino-4-trifluoromethylcoumarin
7-amino-4-(trifluoromethyl)chromen-2-one
Coumarin 151,laser grade
EINECS 258-599-1
2H-1-Benzopyran-2-one, 7-amino-4-(trifluoromethyl)-

Biological Activity

[Description]:

7-Amino-4-(trifluoromethyl)coumarin (AFC, Coumarin 151) is a fluorescent marker for the sensitive detection of proteinases. The excitation and emission wavelengths are 400 and 490 nm, respectively.

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Others

Dye Reagents

[In Vitro]

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[1]. 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[2].

[References]

[1]. Tao Z, et al. Caspase activation by anticancer drugs: the caspase storm. Mol Pharm. 2007 Jul-Aug;4(4):583-95.

[2]. White IN, et al. A continuous fluorometric assay for gamma-glutamyltranspeptidase. Anal Biochem. 1996 Jan 1;233(1):71-5.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.5±0.1 g/cm3

[ Boiling Point ]:
314.6±42.0 °C at 760 mmHg

[ Melting Point ]:
221-222 °C(lit.)

[ Molecular Formula ]:
C₁₀H₆F₃NO₂

[ Molecular Weight ]:
229.155

[ Flash Point ]:
144.1±27.9 °C

[ Exact Mass ]:
229.035065

[ PSA ]:
56.23000

[ LogP ]:
1.64

[ Vapour Pressure ]:
0.0±0.7 mmHg at 25°C

[ Index of Refraction ]:
1.562

MSDS

Click to get detail MSDS

Safety Information

[ Hazard Codes ]:
Xn:Harmful;

[ Risk Phrases ]:
R20/21/22;R36/37/38

[ Safety Phrases ]:
S26-S36-S37/39

[ WGK Germany ]:
3

[ HS Code ]:
2932209090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2932209090

[ Summary ]:
2932209090. other lactones. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%