
5-Dodecanoylaminofluorescein | CAS 107827-77-0
| Catalog Number | A16-0072 |
| Category | Lipid Fluorescent Probes |
| Molecular Formula | C32H35NO6 |
| Molecular Weight | 529.62 |
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Product Introduction
5-Dodecanoylaminofluorescein is an amine-reactive fluorophore that belongs to the xanthene dye class, characterized by its conjugated aromatic system and distinctive spectral properties. It exhibits green fluorescence upon excitation, making it suitable for applications in fluorescence microscopy and flow cytometry. This compound is commonly used in the labeling of biomolecules, where its dodecanoyl chain facilitates membrane association, enhancing its utility in membrane-related studies and intracellular tracking.
Chemical Information
Product Specification
Application
Chemical Information
| Synonyms | DAF; N-(3',6'-dihydroxy-3-oxospiro[2-benzofuran-1,9'-xanthene]-5-yl)dodecanamide |
| SMILES | CCCCCCCCCCCC(=O)NC1=CC2=C(C=C1)C3(C4=C(C=C(C=C4)O)OC5=C3C=CC(=C5)O)OC2=O |
| InChI | InChI=1S/C32H35NO6/c1-2-3-4-5-6-7-8-9-10-11-30(36)33-21-12-15-25-24(18-21)31(37)39-32(25)26-16-13-22(34)19-28(26)38-29-20-23(35)14-17-27(29)32/h12-20,34-35H,2-11H2,1H3,(H,33,36) |
| InChIKey | VJNRUQFWKRLMSL-UHFFFAOYSA-N |
Product Specification
| Excitation | 553 |
| Emission | 575 |
Application
5-Dodecanoylaminofluorescein is a fluorescein-based labeling dye bearing a long-chain dodecanoyl amide, which increases hydrophobic character and supports incorporation into lipid-like environments. In fluorescence workflows, this reagent is commonly used as a membrane-associated tracer for visualizing transport, uptake, and retention in hydrophobic or amphiphilic systems, where fluorescein provides strong visible emission under standard fluorescein excitation conditions. Its amide functionality also makes it a practical fluorescent component for constructing hydrophobic conjugates and staining reagents used in microscopy and materials studies.
1. Membrane Tracing Studies
5-Dodecanoylaminofluorescein is frequently used by cell biology and membrane biophysics groups as a fluorescent tracer to monitor association with lipid-rich membranes and membrane-adjacent compartments. Researchers incorporate the dye into labeling protocols to visualize how amphiphilic fluorescent species partition into membranes, enabling qualitative tracking of localization patterns during incubation and wash steps. Because fluorescein emission is readily imaged with common epifluorescence and confocal setups, the dye is also used to compare relative membrane association across experimental conditions such as formulation changes, incubation time, or surface chemistry of membrane-mimicking materials.
2. Lipid-Based Probe Development
5-Dodecanoylaminofluorescein is applied in the development of lipid-like fluorescent probes for studying delivery and distribution in model membranes, liposomes, and amphiphilic assemblies. Materials scientists and chemical biology teams use the dye as a hydrophobic fluorescent component to prepare labeled lipid formulations that can be imaged to follow vesicle behavior, membrane mixing, or retention within lipid phases. The long-chain dodecanoyl group helps drive partitioning into hydrophobic domains, which is particularly useful when the goal is to report on lipid-phase localization rather than purely aqueous labeling.
3. Biomaterial Surface Labeling
5-Dodecanoylaminofluorescein supports fluorescence labeling of hydrophobic or amphiphilic biomaterial surfaces, including polymer films and membrane-mimetic coatings, where fluorescent signal arises from dye retention within or at the material interface. Researchers use the dye to visualize surface coverage, coating uniformity, and spatial distribution of fluorescently labeled materials under microscopy. This makes it useful for workflow development in biomaterials characterization, including comparative studies of surface modification strategies that influence dye uptake or interfacial residence.
4. Fluorescence Imaging Standards
5-Dodecanoylaminofluorescein is also used as a practical fluorescein-based reference dye in imaging and fluorescence assay development workflows, particularly when a membrane-associated fluorescent behavior is desired in the reference material. Imaging method developers and assay engineers may prepare labeled reference samples to validate microscope alignment, filter set performance, and day-to-day imaging consistency for fluorescein-channel experiments. The dye's incorporation into hydrophobic test matrices can provide a stable, visually trackable reference format for method qualification and troubleshooting in fluorescence microscopy studies.
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