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Coumarin 151

CAS 53518-15-3 ≥99%

Coumarin 151 | CAS 53518-15-3 | ≥99%

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Technical Specifications

CAS Number 53518-15-3
EC / EINECS Number 258-599-1
MDL Number MFCD00006858
SMILES C1=CC2=C(C=C1N)OC(=O)C=C2C(F)(F)F
InChI InChI=1S/C10H6F3NO2/c11-10(12,13)7-4-9(15)16-8-3-5(14)1-2-6(7)8/h1-4H,14H2
InChIKey JBNOVHJXQSHGRL-UHFFFAOYSA-N
PubChem CID 100641
Molecular Formula C₁₀H₆F₃NO₂
Molecular Weight 229.16 g/mol
Melting Point 221-222 °C
Solubility Soluble in DMSO, DMF, methanol. Insoluble in water
Purity ≥99%
Physical Form Light-yellow to yellow powder
HS Code 2932.20
Shelf Life Retest period: 36 months from date of manufacture
Storage Conditions Store in a cool, dry place in a tightly sealed container, protected from light

Product Description & Scientific Applications

7-Amino-4-(trifluoromethyl)coumarin (AFC; Coumarin 151) is a 7-aminocoumarin dye with a trifluoromethyl group at the 4-position. It is supplied as the free amine, and is used to build fluorogenic protease substrates and to calibrate the assays that use them.

Building substrates. The 7-amino group is coupled through an amide bond to the C-terminus of a peptide. The conjugate does not fluoresce, because acylating the amine quenches the dye. A protease that cuts the peptide liberates the reporter amine and fluorescence rises, in proportion to enzyme activity.

Calibrating assays. Free AFC is the standard used to convert assay fluorescence into the amount of product released.

Making stocks. AFC dissolves in DMSO, DMF and methanol and is insoluble in water, so stocks are prepared in DMSO and diluted into buffer.

Reading the signal. Absorbs at 371 nm and emits at 508 nm, the same in water as in methanol. Assay protocols excite at 400 nm and read at 505 nm.

Enzymes measured this way. Caspase-3 and -7 with Ac-DEVD-AFC. Cathepsin B with z-ARR-AFC. Live-cell counts with GF-AFC, which reads alongside rhodamine 110 for dead cells in the same well.

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Safety Information

GHS Pictograms
GHS07 Harmful/Irritant
Signal Word Warning
Hazard Class Not regulated for transport
Transport Category Not classified as dangerous goods for transport (ADR/IATA/IMDG)
H-Statements H315 - H319 - H335
P-Statements P261 - P264 - P271 - P280 - P302+P352 - P305+P351+P338 - P332+P313 - P337+P313 - P362+P364 - P501

Documentation

Safety Data Sheet Download PDF
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