![2-amino-3',6'-dihydroxyspiro[isoindoline-1,9'-xanthen]-3-one](https://resource.bocsci.com/structure/98907-26-7.gif)
2-amino-3',6'-dihydroxyspiro[isoindoline-1,9'-xanthen]-3-one | CAS 98907-26-7
| Catalog Number | A14-0085 |
| Category | Calcium, Chloride and Other indicators |
| Molecular Formula | C20H14N2O4 |
| Molecular Weight | 346.34 |
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Product Introduction
Resorufin precursor fluorescing bright red upon oxidation. Used as a sensitive fluorogenic substrate for enzymatic assays.
Chemical Information
Application
Computed Properties
Patents
Chemical Information
| Synonyms | N-Aminofluorescein; 2-amino-3',6'-dihydroxyspiro[isoindole-1,9'-xanthen]-3(2H)-one; 2-amino-3',6'-dihydroxyspiro[isoindole-3,9'-xanthene]-1-one; 2'-Amino-3,6-dihydroxyspiro[9H-xanthene-9,1'-isoindoline]-3'-one |
| IUPAC Name | 2-amino-3',6'-dihydroxyspiro[isoindole-3,9'-xanthene]-1-one |
| SMILES | C1=CC=C2C(=C1)C(=O)N(C23C4=C(C=C(C=C4)O)OC5=C3C=CC(=C5)O)N |
| InChI | InChI=1S/C20H14N2O4/c21-22-19(25)13-3-1-2-4-14(13)20(22)15-7-5-11(23)9-17(15)26-18-10-12(24)6-8-16(18)20/h1-10,23-24H,21H2 |
| InChIKey | CHYVTSCIBXXQJT-UHFFFAOYSA-N |
Application
2-amino-3',6'-dihydroxyspiro[isoindoline-1,9'-xanthen]-3-one is a spirocyclic fluorescent dye scaffold commonly used in fluorescence labeling workflows where a rigid, photoactive framework helps maintain strong emission under typical assay conditions. The molecule's amino functionality supports chemical derivatization for conjugate preparation, while the dihydroxy substituents provide handles for tuning dye behavior in labeling and staining formats. Researchers leverage this dye building block to construct fluorescent conjugates for microscopy and fluorescence-based readouts, including probe and reagent development where stable fluorescence is required.
1. Fluorescent Conjugate Labeling
2-amino-3',6'-dihydroxyspiro[isoindoline-1,9'-xanthen]-3-one is frequently incorporated into fluorescent conjugates for labeling proteins, peptides, and other biomolecules in chemical biology and materials research. The dye's amino group enables downstream coupling strategies that produce fluorescent bioconjugates for tracking reagent distribution, monitoring binding in assay development, and generating labeled standards for fluorescence workflows. Typical users include academic groups and assay development teams preparing fluorescent reagents for imaging studies and fluorescence readouts in microplate formats.
2. Fluorescence Microscopy Staining
2-amino-3',6'-dihydroxyspiro[isoindoline-1,9'-xanthen]-3-one is used as a fluorescence staining component in microscopy experiments where a bright, spirocyclic dye framework can provide robust cellular or biomaterial visualization. Researchers employ dye-labeled biomolecules or dye-modified materials to highlight structures of interest, support co-localization studies, and create fluorescent labeling reagents for fixed-sample imaging workflows. This application is particularly relevant for teams developing staining protocols for microscopy-based characterization of labeled targets in cell biology, biomaterials, and imaging reagent optimization.
3. Fluorescence-Based Bioassay Development
2-amino-3',6'-dihydroxyspiro[isoindoline-1,9'-xanthen]-3-one supports fluorescence assay development where fluorescent signal generation from labeled reagents is the primary readout. In practice, developers use dye-conjugated components to build fluorescence-based binding assays, labeling-dependent detection reagents, and fluorescence imaging compatible assay reagents for method development. The spirocyclic dye scaffold and derivatizable amino functionality make it useful for constructing assay reagents that require consistent fluorescence response across labeling batches and experimental runs.
4. Fluorescent Probe Construction
2-amino-3',6'-dihydroxyspiro[isoindoline-1,9'-xanthen]-3-one is also used as a fluorophore building block in fluorescent probe construction for molecular imaging reagent development. Teams in chemical biology and fluorescence technology use the dye scaffold to generate probe conjugates that report on labeled biomolecular interactions or serve as fluorescent tags within larger probe architectures. This is common in workflows where researchers need a derivatizable fluorescent core that can be incorporated into custom probe formats for microscopy, imaging assays, and fluorescence-based characterization studies.
Computed Properties
| XLogP3 | 2.3 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 0 |
| Exact Mass | 346.09535693 g/mol |
| Monoisotopic Mass | 346.09535693 g/mol |
| Topological Polar Surface Area | 96Ų |
| Heavy Atom Count | 26 |
| Formal Charge | 0 |
| Complexity | 558 |
| 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 |
|---|---|---|
| US-2020392148-A1 | Chemosensor and a method of detecting palladium ions | 2019-06-12 |
| US-11124522-B2 | Chemosensor and a method of detecting palladium ions | 2019-06-12 |
| US-2017276607-A1 | Fluorescent schiff base conjugate cu(ii) chemosensors and methods thereof | 2016-03-28 |
| US-2018194944-A1 | Method for making schiff base | 2016-03-28 |
| US-9994713-B2 | Fluorescent schiff base conjugate Cu(II) chemosensors and methods thereof | 2016-03-28 |
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