
7-Amino-4-methylcoumarin | CAS 26093-31-2
| Catalog Number | A17-0066 |
| Category | Laser Dyes |
| Molecular Formula | C10H9NO2 |
| Molecular Weight | 175.18 |
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Product Introduction
7-Amino-4-methylcoumarin is a high-brightness fluorescent dye and key building block for custom probe synthesis. Partner with a leading fluorescent probe supplier to access reliable fluorescent labeling reagents for bioimaging.
Chemical Information
Product Specification
Application
Computed Properties
Literatures
Patents
Chemical Information
| Synonyms | 7-amino-4-methyl-1-benzopyran-2-one; 7-amino-4-methylchromen-2-one |
| Purity | ≥ 98 % (HPLC) |
| IUPAC Name | 7-amino-4-methylchromen-2-one |
| SMILES | CC1=CC(=O)OC2=C1C=CC(=C2)N |
| InChI | InChI=1S/C10H9NO2/c1-6-4-10(12)13-9-5-7(11)2-3-8(6)9/h2-5H,11H2,1H3 |
| InChIKey | GLNDAGDHSLMOKX-UHFFFAOYSA-N |
| Solubility | Soluble in DMSO, Methanol |
| Density | 1.275 g/cm3 |
| Appearance | Slight yellow powder |
| Boiling Point | 378.3 °C at 760 mmHg |
| Melting Point | 223-232 °C |
| LogP | 2.26480 |
Product Specification
| Storage | Store at 2-8 °C |
| Signal | Warning |
| GHSHazardStatements | H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation] H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation] H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation] |
| Precautionary Statement Codes | P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (The corresponding statement to each P-code can be found at the GHS Classification page.) |
Application
7-Amino-4-methylcoumarin is a coumarin-based fluorescent dye featuring an aniline (amino) substituent that enables straightforward derivatization and incorporation into labeled constructs used in fluorescence-based assays and microscopy workflows. Its coumarin scaffold is widely used as a bright, photostable fluorophore platform for building conjugates, standards, and fluorescence readouts where excitation in the visible range and emission in the blue-to-green region are advantageous. In practice, this dye is selected when researchers need a reactive fluorophore handle for preparing fluorescent conjugates and imaging reagents.
1. Fluorescent Labeling Reagents
7-Amino-4-methylcoumarin is frequently used as a fluorophore building block for preparing fluorescent labeling reagents for proteins, peptides, and other biomolecules in chemical biology and materials research. The amino functionality supports downstream coupling strategies that yield dye-labeled conjugates for tracking biomolecule distribution, monitoring binding events, and generating fluorescent standards for assay development. Researchers often incorporate this coumarin dye into conjugates used in endpoint fluorescence measurements and imaging experiments where a coumarin emission profile provides clear signal separation from background autofluorescence.
2. Fluorescence Microscopy Staining
7-Amino-4-methylcoumarin is applied as a coumarin fluorophore component in microscopy staining workflows, particularly when labeled biomolecules are used as imaging probes for cellular structures or extracellular components. Laboratories commonly prepare dye-conjugated targeting reagents (for example, dye-tagged affinity reagents or dye-labeled polymers) and use them in fluorescence imaging to visualize localization patterns. This dye's small, rigid coumarin core helps maintain strong fluorescence in many labeling contexts, making it a practical choice for constructing microscopy stains and fluorescent tracers used in fixed-sample imaging and imaging reagent development.
3. Fluorescence Bioassay Development
7-Amino-4-methylcoumarin is also used in fluorescence assay development where coumarin-based readouts provide robust endpoint or kinetic signals for monitoring biochemical workflows. Researchers incorporate the dye into assay reagents such as fluorescently labeled substrates, detection tags, or calibration materials to support fluorescence readout in plate-based formats. In these applications, the dye's role is typically to provide a stable fluorescence reporter that can be integrated into custom assay architectures for screening, method optimization, and fluorescence-based quantification.
4. FRET Pair Construction
7-Amino-4-methylcoumarin is commonly used as a donor fluorophore component when building FRET-based systems for fluorescence resonance energy transfer experiments. By using the amino handle to create donor-labeled constructs, researchers can assemble donor-acceptor pairs in labeled biomolecules, polymer systems, or molecular assemblies designed for distance- or proximity-dependent fluorescence changes. This coumarin platform is particularly useful during probe and sensor construction when a visible-excitation donor is needed to pair with an appropriate acceptor dye for ratiometric or signal-suppression readouts.
Computed Properties
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 0 |
| Exact Mass | 175.063328530 g/mol |
| Monoisotopic Mass | 175.063328530 g/mol |
| Topological Polar Surface Area | 52.3Ų |
| Heavy Atom Count | 13 |
| Formal Charge | 0 |
| Complexity | 260 |
| 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 |
Literatures
| PMID | Publication Date | Title | Journal |
|---|---|---|---|
| 22925447 | 2012-09-15 | Structure-anti-leukemic activity relationship study of ortho-dihydroxycoumarins in U-937 cells: key role of the δ-lactone ring in determining differentiation-inducing potency and selective pro-apoptotic action | Bioorganic & medicinal chemistry |
| 22517611 | 2012-06-04 | Dual-luminophore-labeled gold nanoparticles with completely resolved emission for the simultaneous imaging of MMP-2 and MMP-7 in living cells under single wavelength excitation | Chemistry (Weinheim an der Bergstrasse, Germany) |
| 22402981 | 2012-06-01 | Integrin/Fak/Src-mediated regulation of cell survival and anoikis in human intestinal epithelial crypt cells: selective engagement and roles of PI3-K isoform complexes | Apoptosis : an international journal on programmed cell death |
| 22499434 | 2012-06-01 | SERINE proteinase like activity in apolipophorin III from the hemolymph of desert locust, Schistocerca gregaria | Archives of insect biochemistry and physiology |
| 22294421 | 2012-04-01 | Fluorogenic peptide-based substrates for monitoring thrombin activity | ChemMedChem |
Patents
| Publication Number | Title | Priority Date |
|---|---|---|
| CN-115125232-A | A Sensitive Detection Method of Organophosphorus Pesticide Residues Based on Immobilized Organophosphorus Hydrolase | 2022-06-21 |
| CN-114965454-A | A colorimetric fluorescent dual-mode reagent for on-site detection of nitrite | 2022-05-24 |
| CN-115160204-A | A kind of fibroblast activation protein inhibitor and preparation method and application thereof | 2022-05-13 |
| CN-114869863-A | A kind of multifunctional composite scaffold and its preparation method and application | 2022-05-10 |
| CN-114736193-A | A kind of bedaquiline derivative and preparation method thereof | 2022-04-27 |
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