
Coumarin 343 X carboxylic acid | CAS 946123-11-1
| Catalog Number | F06-0003 |
| Category | Coumarin |
| Molecular Formula | C22H26N2O5 |
| Molecular Weight | 398.45 |
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Product Introduction
Coumarin 343 is a blue emitting fluorophore used as a laser dye. The fluorophore can serve as a FRET donor for FAM (fluorescein).
Chemical Information
Product Specification
Application
Computed Properties
Patents
Chemical Information
| Synonyms | 6-({4-Oxo-3-oxa-13-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1,5,7,9(17)-tetraen-5-yl}carbonylamino)hexanoic acid; 6-(11-Oxo-2,3,6,7-tetrahydro-1H,5H,11H-pyrano[2,3-f]pyrido[3,2,1-ij]quinoline-10-carboxamido)hexanoic acid |
| Purity | NMR 1H, HPLC-MS (95%) |
| IUPAC Name | 6-[(4-oxo-3-oxa-13-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1,5,7,9(17)-tetraene-5-carbonyl)amino]hexanoic acid |
| SMILES | C1CC2=C3C(=C4C(=C2)C=C(C(=O)O4)C(=O)NCCCCCC(=O)O)CCCN3C1 |
| InChI | InChI=1S/C22H26N2O5/c25-18(26)8-2-1-3-9-23-21(27)17-13-15-12-14-6-4-10-24-11-5-7-16(19(14)24)20(15)29-22(17)28/h12-13H,1-11H2,(H,23,27)(H,25,26) |
| InChIKey | HCUGYFCWVUOZRK-UHFFFAOYSA-N |
| Solubility | Well soluble in DMF, DMSO, moderately soluble in DCM, DCE, EtOAc, insoluble in diethyl ether. |
| Appearance | yellow crystals |
Product Specification
| ε, L⋅mol-1⋅cm-1 | 39000 |
| Fluorescence Quantum Yield | 0.63 |
| Excitation | 437 |
| Emission | 477 |
| Storage | 24 months after receival at -20°C in the dark. Transportation: at room temperature for up to 3 weeks. Avoid prolonged exposure to light. |
Application
Coumarin 343 X carboxylic acid is a coumarin-based fluorescent dye bearing a carboxylic acid functionality that supports covalent attachment to amine-containing biomolecules and labeling handles in fluorescence workflows. Its strong fluorescence in the visible/near-UV range makes it a common choice for constructing fluorescent conjugates used in microscopy, labeling studies, and fluorescence-based assay development where a coumarin fluorophore is preferred. The dye format is especially useful when downstream conjugates require a defined attachment site rather than passive adsorption.
1. Fluorescent Labeling Conjugates
Coumarin 343 X carboxylic acid is used to prepare fluorescent labeling conjugates for proteins, peptides, and other amine-bearing targets in chemical biology and biomaterials research. Researchers typically incorporate the carboxylic acid functionality to enable covalent coupling strategies that yield stable dye-biomolecule conjugates for tracking, binding studies, and reagent construction. In practice, this supports workflows where the dye must remain associated with the labeled macromolecule during washing, incubation, and imaging steps, such as fluorescent tagging of affinity reagents, labeling standards, and conjugate-based characterization experiments.
2. Fluorescence Microscopy Imaging
Coumarin 343 X carboxylic acid is applied in fluorescence microscopy to visualize labeled biomolecules and surface-associated materials with coumarin emission. Users in cell biology, materials science, and analytical imaging often rely on coumarin dyes to generate clear fluorescence contrast for localization studies, including labeling of biomaterial coatings, fluorescent tracking of conjugated probes in microenvironments, and imaging of prepared samples where excitation and emission are compatible with their microscope filter sets. The carboxylic acid group also facilitates consistent conjugate preparation for imaging experiments that require defined dye attachment rather than noncovalent staining.
3. Fluorescence-Based Bioassays
Coumarin 343 X carboxylic acid is frequently incorporated into fluorescence assay development as a reporter dye for monitoring binding, labeling efficiency, and assay readouts in microplate and cuvette-based formats. In chemical biology workflows, the dye is used to generate fluorescent conjugates that serve as assay reagents, enabling fluorescence measurement after incubation and separation steps. This approach is particularly common when a coumarin fluorophore is chosen for its excitation/emission compatibility with standard fluorescence instrumentation and when covalently attached dye conjugates are needed to reduce dye loss and improve reproducibility across assay runs.
4. Surface And Polymer Functionalization
Coumarin 343 X carboxylic acid supports fluorescent surface functionalization and polymer labeling for materials characterization and imaging. Researchers use the dye to introduce fluorescent tags onto polymer backbones, coatings, and biomaterial surfaces through covalent coupling to available reactive groups, enabling visualization of functional layers and tracking of labeled components in engineered constructs. This application is common in biomaterials science and industrial R&D settings where fluorescence provides a practical readout for coating uniformity, material processing verification, and spatial localization of functionalized surfaces.
Computed Properties
| XLogP3 | 3.4 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 6 |
| Rotatable Bond Count | 7 |
| Exact Mass | 398.18417193 g/mol |
| Monoisotopic Mass | 398.18417193 g/mol |
| Topological Polar Surface Area | 95.9Ų |
| Heavy Atom Count | 29 |
| Formal Charge | 0 |
| Complexity | 691 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Covalently-Bonded Unit Count | 1 |
| Compound Is Canonicalized | Yes |
Patents
| Publication Number | Title | Priority Date |
|---|---|---|
| EP-1842923-A1 | Methanesulfonylaminoindole derivatives and labeled oligonucleotide probes containing them. | 2006-02-20 |
| EP-1842923-B1 | Methanesulfonylaminoindole derivatives and labeled oligonucleotide probes containing them | 2006-02-20 |
| US-2007196852-A1 | Labeling reagent | 2006-02-20 |
| US-7759470-B2 | Labeling reagent | 2006-02-20 |
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