This compound belongs to the class of organic compounds known as xanthenes. These are polycyclic aromatic compounds containing a xanthene moiety, which consists of two benzene rings joined to each other by a pyran ring.
External Descriptors
Not available
1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.
Certificati (CoA, COO, BSE/TSE e tabella di analisi)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Proprietà chimiche e fisiche
Peso molecolare
662.900 g/mol
XLogP3
5.500
Hydrogen Bond Donor Count
3
Hydrogen Bond Acceptor Count
6
Rotatable Bond Count
0
Exact Mass
662.717 Da
Monoisotopic Mass
658.721 Da
Topological Polar Surface Area
102.000 Ų
Heavy Atom Count
30
Formal Charge
0
Complexity
681.000
Isotope Atom Count
0
Defined Atom Stereocenter Count
0
Undefined Atom Stereocenter Count
0
Defined Bond Stereocenter Count
0
Undefined Bond Stereocenter Count
0
The total count of all stereochemical bonds
0
Covalently-Bonded Unit Count
1
Calcolatori di soluzioni
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Recensioni
Recensioni dei clienti
Application Protocols
No tested biological assay protocols are provided for this SKU. Performance parameters such as recommended dilutions, imaging settings, or control samples are application-specific and should be determined empirically.
General starting points (guidance only):
Stock solutions: Prepare 1–10 mM in anhydrous DMSO or DMF. Filter (0.2 µm PTFE) if needed. Protect from light.
Spectroscopy: Verify λmax and fluorescence response in your exact solvent and pH; prepare calibration curves to account for inner-filter effects at higher concentrations.
Conjugation trials: Begin with 1–2 equiv dye relative to activated partner; pH 7.5–8.5 for aqueous EDC/NHS workflows, or 2–3 equiv base in DMF for HATU/HBTU couplings. Optimize by small-scale screens.
For validated, application-specific protocols, consult the primary literature appropriate to your system.
Biological Roles
Item-specific biological roles are not applicable; this is a synthetic research dye. No biological function or clinical use is claimed.
General biochemical context (literature):
Xanthene dyes (fluorescein/eosin family) are widely used as fluorescent reporters due to strong visible absorption and environment-sensitive emission. The presence of ionizable phenolic/fluorone groups yields pH-dependent fluorescence, often maximized near neutral to mildly basic pH.
The primary amine in 5-aminated dyes enables facile bioconjugation to carboxyl-bearing biomolecules via amide formation (through activated esters) or to aldehyde-modified glycans via reductive amination after appropriate linker strategies. For direct protein labeling, N-hydroxysuccinimide esters of the dye are typically used; with a dye that itself bears a primary amine, one may instead couple to activated carboxyls on biomaterials or convert the amine to isothiocyanate for lysine labeling (general chemistry; ensure compatibility with your system).
Photophysical behavior can be modulated by microenvironment (protein binding, solvent polarity, aggregation), which in turn affects quantum yield and lifetime—important for sensor design and fluorescence readouts.
Note: Any use in biological systems should be validated by the end user. This product is for research use only.
Buffer Applications
Not typically used as a buffer component. However, eosin/fluorescein-type dyes exhibit pH-dependent spectral changes, so buffer choice can influence performance.
Practical guidance (general):
For spectroscopic work, select buffers with low UV/Vis absorbance in the visible region (e.g., phosphate, HEPES, borate), and avoid components that strongly quench fluorescence (e.g., high concentrations of transition metals).
pH considerations: Fluorescein/eosin derivatives often display strong fluorescence near neutral to mildly basic pH; verify optimal pH for your specific application via a pH titration in your matrix.
Ionic strength: High salt can influence dye aggregation; maintain consistent ionic strength across measurements for reproducibility.
Recipes and quantitative buffer parameters are application-dependent and not specified for this item; consult primary sources for buffer preparation.
Green Alternatives
Perspective on greener choices (literature/general):
Role of 5-Aminoeosin: A visible-light-absorbing xanthene dye that can act as an organophotocatalyst, often enabling room-temperature transformations under mild conditions and replacing precious-metal photocatalysts in some cases.
Alternative catalysts/labels (trade-offs):
Riboflavin (vitamin B2) and flavin derivatives: bio-derived, benign, effective in certain aerobic oxidations; narrower reaction scope and different redox potentials than eosin.
Rose Bengal: halogenated xanthene with strong absorption; effective for singlet oxygen generation; may be more phototoxic and can undergo faster photobleaching in some systems.
4CzIPN (organic donor–acceptor photocatalyst): metal-free with tunable redox properties; synthesis and cost may be higher; different solubility profile.
Eosin Y (without amino handle): simpler handling if no conjugation is needed; lacks the primary amine for covalent attachment.
Solvent and process greening:
Prefer water/EtOH or water/MeCN with minimal DMSO/DMF where possible; adjust pH to maximize dye solubility and performance.
Flow photochemistry can increase photon efficiency and reduce over-irradiation, lowering byproducts.
Use LED sources at the dye’s absorption band to cut energy consumption and heat.
Small comparison (general attributes, not specifications):
5-Aminoeosin: organocatalyst + conjugation handle; good visible absorption; tunable via pH and environment.
Metal photocatalysts (e.g., Ru/Ir): broad scope but rely on critical metals; challenging sustainability profile.
Flavins: greener feedstock, but narrower scope and often oxygen-dependent.
Pharmaceutical Uses
No pharmacopeial grade or excipient status is specified for this item; it is offered for research use only.
General formulation context (literature/industry practice):
Xanthene dyes are occasionally used as colorants or analytical tracers in process development; however, regulatory acceptance depends on identity, purity, residual solvents/metals, and toxicology. 5-Aminoeosin, with a reactive amine, is more commonly a synthetic intermediate for derivatizing eosin chromophores rather than a direct excipient.
In drug delivery/materials R&D, amino-functionalized dyes are used to fabricate fluorescently labeled polymers, nanoparticles, or hydrogels to track distribution or release profiles in non-clinical studies.
If pharmaceutical or diagnostic use is contemplated, qualification to appropriate standards (e.g., compendial testing, elemental impurities, residual solvent limits, microbial limits, and photostability studies) would be required. This SKU does not provide such specifications; refer to the CoA and your quality system.
Physical Properties
Item-specific specifications
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
Literature/general properties for eosin-type amino xanthene dyes (for context only; not item specifications):
Physical form: typically colored solid (orange to red hues common for eosin derivatives).
Solubility: often soluble in polar organic solvents (DMF, DMSO, alcohols); water solubility depends strongly on ionization state and counterion (free acids typically sparingly soluble; salts more soluble).
Photophysics: eosin-type chromophores show strong visible absorption (λmax commonly near ~510–525 nm) and green fluorescence; quantum yield and λmax vary with solvent and pH (literature).
Acid–base behavior: fluorescein/eosin cores are pH-sensitive; phenolic/fluorone groups display multiple pKa values leading to marked spectral shifts (literature). Exact pKa values depend on substitution and medium.
Partitioning: logP/logD vary with ionization; anionic forms are more hydrophilic, neutral forms more hydrophobic (literature trend).
Do not treat the above as specifications. For authoritative, lot-specific data (including any UV/Vis characteristics, purity, residual solvents, water, and metals), consult the item’s CoA/SDS.
Quality and Grades
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Guidance on interpreting quality for dye reagents (general):
Research grade: typically supports synthetic, analytical, and materials R&D. Exact assay purity, residual metals, inorganic salts, and moisture are specified on the CoA. When dyes are used as photoredox catalysts or labeling agents, spectral purity (absence of nonfluorescent chromophores) and counterion identity can affect performance.
Chromatographic purity: for spectroscopic or photoredox use, low levels of colored impurities are desirable to avoid inner-filter effects and quenching.
Stabilizers: Some dye materials are supplied without stabilizers; others may include trace stabilizers or specific counterions to improve solubility or stability. If stabilizers or salt forms are used, they will be listed on the CoA/SDS. None are specified here for this item.
Batch-to-batch consistency: verify λmax, extinction coefficient, and fluorescence response in your chosen solvent/pH as part of incoming QC if these metrics are critical to your application.
Documentation:
For concrete numerical values (assay, water, metals, UV cutoffs, residual solvents), this listing does not specify them. Refer to the lot-specific CoA and SDS for authoritative details.
Reaction and Applications
This compound combines the eosin chromophore with a primary amine, enabling both photochemical applications and covalent conjugation.
Applications (literature/general for amino-eosin dyes):
Conjugation chemistry: The aniline –NH2 allows formation of amides (with activated esters such as NHS esters), ureas (with carbamoyl chlorides), and thioureas/isothiocyanates (via reaction with thiophosgene-equivalents). Useful for attaching the dye to carboxylated polymers, nanoparticles, or linkers.
Surface/materials labeling: Amide coupling to carboxyl-functional surfaces (e.g., EDC/NHS activation on polymers, silica with carboxylates) to embed an eosin chromophore in materials for sensing or photonic applications.
Photoredox catalysis: Eosin scaffolds are established visible-light organophotocatalysts for reductive and oxidative quenching cycles (e.g., C–H functionalization, C–C bond formation, atom transfer variants). The amino substituent can tune redox/solubility properties relative to eosin Y (literature context).
Spectroscopic probes: The eosin/fluorescein family exhibits environment- and pH-sensitive absorption/fluorescence, enabling use in optical sensors when immobilized or conjugated.
Practical tips:
Minimize light exposure during setup to reduce background photoreactions; use amber glassware when feasible.
For amide couplings, mildly basic conditions (e.g., DIPEA, pH 7.5–8.5 in aqueous-organic systems) help maintain dye solubility while preserving reactive esters.
For photoredox, degas solutions (N2 or Ar sparge) when oxygen-sensitive; conversely, some eosin-catalyzed oxidations use O2 as the terminal oxidant—match atmosphere to mechanism.
Verify spectral purity of the dye in your solvent (UV/Vis) before critical experiments to ensure consistent photochemical performance.
Reaction Conditions
General conditions from literature/practice for analogous amino-xanthene dyes (guide only; not item specifications):
Amide coupling to carboxylates (materials/bioconjugation):
Solvent: DMF, DMSO, or aqueous buffer/DMF mixtures.
Activators: EDC/NHS (aqueous), HATU/HBTU/DIC (organic); base such as DIPEA or triethylamine (2–4 equiv relative to dye).
Temperature: 20–25 °C; 2–16 h depending on partners. Protect from light.
Isothiocyanate formation (to make a reactive labeling dye):
Reagents: thiophosgene or safer surrogates (e.g., 1,1′-thiocarbonyldiimidazole) under anhydrous conditions.
Solvent: dry DCM/MeCN/THF or DMF.
Temperature: 0 °C to rt; monitor by TLC/LC–MS. Quench and purify under low light.
Photoredox catalysis using eosin-type dyes:
Light source: green LEDs (e.g., 520–535 nm) matched to dye absorption.
Solvents: MeCN, MeOH, DMSO, or aqueous mixtures depending on substrates.
Additives: sacrificial electron donors/acceptors (e.g., DIPEA, TEA) or O2 depending on mechanism.
Atmosphere: inert (Ar/N2) for reductive quenching; oxygen for aerobic oxidations.
Temperature: ambient; reaction times from 1–24 h based on substrate and light intensity.
Analytical checks: UV/Vis to confirm dye integrity and concentration; LC–MS or HPLC to monitor conversion. Always run small-scale trials to optimize equivalents and pH.
Note: Verify compatibility of reagents with the dye’s phenolic/halogenated core to avoid undesired side reactions.
Safety and Handling
Safety summary (item-specific):
GHS classification, signal word, pictograms, and H-statements: Not specified for this item; refer to SDS.
Storage conditions (product data): Store at room temperature. Protect from light to maintain dye integrity (good practice for xanthene dyes).
General safety considerations for eosin/fluorescein-type dyes (literature/good laboratory practice; not a substitute for SDS):
Avoid inhalation of dust and contact with skin/eyes. Wear appropriate PPE: lab coat, safety glasses, and suitable gloves (e.g., nitrile).
Handle under low-light or amber lighting when preparing stock solutions to minimize photobleaching/photooxidation.
Incompatibilities: strong oxidizers/reductants may degrade the chromophore; strong bases/acids can alter ionization and cause spectral/solubility changes. Avoid reactive acylating/chlorinating agents unless intended for derivatization.
Thermal stability: dyes are generally stable at ambient conditions but can decompose upon prolonged heating or intense light exposure.
First aid (overview): in case of contact, rinse with water for 15 minutes; if inhaled, move to fresh air; if ingested, rinse mouth and seek medical attention. Always follow SDS instructions.
Waste: dispose of dye-containing solutions and solids as organic hazardous waste in accordance with institutional and local regulations.
Authoritative safety information is found exclusively in the SDS for this SKU.
Solvent Selection
Context for 5-Aminoeosin (general guidance for eosin-type dyes; not item specifications):
Polarity/ionization: The eosin/fluorescein scaffold bears acidic phenolic/fluorone functions; with a primary aniline (–NH2) substituent, the dye’s charge state is pH-dependent. Solubility and spectral properties shift with solvent polarity and pH.
Practical solvent choices:
Stock solutions for reactions/labeling: DMSO or DMF are excellent for preparing concentrated stocks due to high polarity and dye solubilization. Methanol/ethanol can also be suitable at lower concentrations.
Aqueous work: Solubility in water depends on the ionization state and any counterions present. Small percentages of DMSO, DMF, or ethanol can aid dissolution. Adjusting pH to favor the anionic form often increases aqueous solubility for eosin-like dyes.
Nonpolar media: Poorly soluble; consider co-solvents or surfactants if nonpolar matrices are required.
When to choose 5-Aminoeosin vs alternatives:
Choose 5-Aminoeosin when you need an eosin-like chromophore with a built-in primary amine for downstream coupling (amide/urea/thiourea formation) or incorporation into polymers/surfaces.
If you only require a photoredox catalyst without conjugation, eosin Y (no amino handle) or Rose Bengal may suffice.
Comparison (general):
DMSO vs DMF: DMSO typically offers better oxidative stability and lower volatility; DMF can be advantageous for certain coupling chemistries. Both are miscible with water for gradient dilution.
Aqueous buffers: Use pH 7–9 for many fluorescein/eosin dyes to balance solubility and fluorescence; confirm for your system by small-scale trials.
Storage and Reconstitution
Storage temperature (product data): Room temperature.
Light sensitivity: As with most xanthene dyes, store protected from light (amber bottle or foil-wrapped container) to minimize photobleaching.
Atmosphere: Store tightly closed in a dry environment. If frequent opening is expected, consider using a desiccator.
Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
Reconstitution and handling (general):
Prepare concentrated stocks (e.g., 1–10 mM) in dry DMSO or DMF; aliquot and store protected from light. For aqueous work, adjust pH and/or include a small percentage of co-solvent to aid dissolution.
Freeze–thaw: If solutions are stored cold, minimize freeze–thaw cycles by aliquoting. Allow solutions to equilibrate to room temperature before opening to avoid condensation.
Shelf life: Not specified for this item; verify integrity by UV/Vis (absorption profile) before critical experiments. Discard if significant degradation or precipitation is observed.
Always consult the SDS and CoA for lot-specific guidance and stability information. This product is for research use only.
Structure and Identity
Brief overview: 5-Aminoeosin is an amino-functionalized xanthene dye derived from the eosin/fluorescein scaffold. The primary amine provides a convenient handle for conjugation and materials modification while retaining the eosin chromophore.
Product name: 5-Aminoeosin (research grade)
CAS: 75900-75-3 (product data)
PubChem CID: 44150682 (product data)
InChIKey: 36874 (product data as provided)
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
Structural features (general, literature):
Core: xanthene/fluorone framework related to fluorescein/eosin dyes.
Substitution: eosin-type tetrabrominated fluorescein core; the “5-amino” descriptor indicates a primary aryl amine substituent on the ring system (literature description for amino-eosin derivatives). Exact regiochemistry and counterions should be confirmed from the CoA.
Functional groups: phenolic/fluorone oxygen functionalities, multiple aryl bromides (typical for eosin), and a primary aniline-type amine enabling further derivatization (amide, urea, isothiocyanate, etc.).
2D description: tricyclic xanthene with two fused benzene rings bridged by an oxygenated central ring; peripheral halogens on the outer rings; one ring bearing an aniline –NH2 substituent and phenolic/carboxy-like functionalities characteristic of fluorescein/eosin families.
Notes:
Exact ionization state, salt form (free acid vs salt), and stereochemical descriptors are generally not applicable to xanthene dyes; verify specific lot information on the CoA.
Synthetic Utility
Functional handle and dye core make 5-Aminoeosin a versatile building block for materials and probe synthesis.
Transformations enabled by the –NH2 (general):
Amide bond formation: Couple with activated carboxylic acids (NHS esters, acid chlorides, DIC/EDC-mediated couplings) to attach the dye to polymers, surfaces, or linkers.
Urea/carbamate formation: Reaction with chloroformates or carbamoyl chlorides yields protected or functional ureas/carbamates.
Isothiocyanate generation: Conversion of the aryl amine to an isothiocyanate (e.g., via thiophosgene surrogates) affords an electrophilic dye tag compatible with lysine labeling on proteins (general method).
Diazonium chemistry: Anilines can be diazotized to form azo linkages; exercise caution given the complex dye core.
Utility of the eosin core:
Provides a robust visible chromophore/fluorophore for tracking and analytics.
Halogenated xanthene framework can modulate intersystem crossing, enabling triplet generation and photosensitization (useful in photoredox and singlet-oxygen processes).
Practical notes:
Maintain moderate temperatures and protect from strong light during coupling to minimize background photoreactions.
Control pH/solvent to balance nucleophilicity of the amine and solubility of the dye (DMF/DMSO, or mixed aqueous-organic systems with mild base).
Purification: Reverse-phase or normal-phase chromatography may be used; dye aggregation and tailing can be mitigated with small amounts of acid/base modifiers.
Target Specificity
Not applicable. This product is a small-molecule dye, not an antibody or affinity reagent. No antigen/epitope, clone, or species reactivity data are provided or implied for this item.
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