This compound belongs to the class of organic compounds known as flavonols. These are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position.
External Descriptors
trihydroxyflavone
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.
Determine the necessary mass, volume, or concentration for preparing a solution.
Dilution Calculator
Determine the dilution needed to prepare a stock solution.
Reconstitution Calculator
Revisões
Avaliações dos Clientes
Application Protocols
No validated, item-specific application protocols are provided in the Product Data for this SKU. The following is general guidance for using 3,6,4'-trihydroxyflavone as a fluorescent ESIPT probe in solution; adjust to your system and instrumentation.
Stock and working solutions (general):
Prepare a 10 mM stock in anhydrous DMSO or ethanol under low light. Store aliquots in amber vials.
For measurements, dilute into the desired solvent/buffer to 1–10 µM (fluorescence) or 10–50 µM (UV–vis). Keep final organic cosolvent ≤1–2% v/v for aqueous assays.
Spectral acquisition:
Typical excitation: 330–370 nm (select band to minimize overlap with buffer/protein absorbance). Record emission 400–650 nm to capture both N* and T* bands.
For ratiometric analysis, compute I_T*/I_N* using peak maxima or integrated areas; calibrate with solvent polarity/H‑bonding standards.
Controls and interferences:
Include blank solvent/cosolvent controls and, for biomolecular studies, proper minus‑probe controls to quantify background fluorescence.
Avoid strong bases or high pH which shift ionization and may alter emission.
Data quality:
Use matched quartz cuvettes; correct for inner‑filter effects at higher concentrations.
Minimize oxygen and light exposure for time‑dependent studies to limit photobleaching/oxidation.
These steps are provided as general literature-based practices and are not validated performance specifications for this SKU.
Biological Roles
Item-specific biological testing is not provided for this SKU. The following summarizes general, literature-based roles of flavonols like 3,6,4'-trihydroxyflavone in biochemistry; it is not a medical or clinical claim.
Natural products context: Flavonols are widespread plant polyphenols functioning as UV‑protective pigments and signaling molecules. The 3‑hydroxyflavone core is a common scaffold in secondary metabolism.
Chemical biology utility: 3‑hydroxyflavone derivatives are widely used as ratiometric fluorescent probes due to ESIPT. 3,6,4'-trihydroxyflavone’s dual emission is sensitive to polarity and hydrogen‑bonding, enabling studies of protein binding pockets, lipid bilayers, micelles, and nucleic acid environments in vitro.
Redox/antioxidant chemistry: Phenolic OH groups can undergo one‑electron transfer and H‑atom donation to reactive radicals; metal chelation at adjacent OH/carbonyl sites can also modulate redox behavior (context for in vitro antioxidant assays). Specific quantitative antioxidant capacity for this exact compound depends on conditions and is not item‑specified.
Enzyme interactions (in vitro): Flavonols may interact with oxidoreductases or binding proteins; such interactions are often exploited to modulate or report on microenvironmental properties via spectral shifts. These are research observations and not validated for therapeutic use.
Important: This product is provided strictly for research use. Do not use in humans or animals, and do not interpret these roles as medical claims.
Buffer Applications
This compound is not a buffer reagent and does not define a specific buffering range. However, it is frequently used as a fluorescent probe in buffered aqueous assays. Practical guidance (general/literature):
Stock preparation:
Prepare concentrated stocks in DMSO or ethanol (e.g., 1–50 mM) under low light. Filter (0.2 µm PTFE) if needed.
Aliquot and store in amber vials to avoid repeated freeze–thaw.
Use in buffers:
Add small volumes of organic stock to the target buffer to achieve final organic cosolvent ≤1–2% v/v when possible (verify assay tolerance). Common buffers: PBS (pH 7.2–7.4), HEPES (pH 7.2–7.6), Tris (pH 7–8). Note that strong hydrogen‑bonding or basic pH can alter ESIPT emission.
For higher apparent solubility at low organic content, consider cyclodextrin inclusion complexes or mild surfactants (e.g., 0.05–0.1% Tween‑20) after validating spectral effects.
pH considerations:
Phenolic deprotonation above pH ~8 can change absorption/emission and promote oxidation; work near neutral pH for reproducible spectra unless studying pH effects intentionally.
Light/oxygen:
Protect cuvettes/well plates from stray light. Degassing or using antioxidant-free, oxygen‑controlled conditions may improve signal stability in long measurements.
Item-specific buffer compatibility data and precise solubility in given buffers are not specified for this SKU; consult CoA/Spec Sheet or perform small‑scale pretests.
Green Alternatives
Because 3,6,4'-trihydroxyflavone is a solid analyte/reagent rather than a process solvent, “greener alternatives” primarily concern solvent choice and synthesis planning rather than replacing the compound itself.
Greener solvent choices for handling and spectroscopy (literature/practice):
Prefer ethanol (bio‑based) over methanol when feasible for spectroscopic measurements, balancing safety and spectral needs.
Acetonitrile (readily recyclable) can substitute for DMF/DMSO in some preparations and analytical runs, though solubility may be lower.
2‑MeTHF or CPME can replace THF/acetone in certain extraction/film‑casting workflows; verify solubility and photophysical impacts.
Comparison (general attributes; not item-specific):
Ethanol vs. Methanol: Ethanol is less toxic and renewable; both are protic and can influence ESIPT—validate spectra.
MeCN vs. DMF/DMSO: MeCN offers easier recovery and lower chronic toxicity but may provide lower solubility.
Water‑based media with cosolvents: Reduce VOCs; use cyclodextrins or micelles to enhance apparent solubility. Monitor pH to prevent phenolate‑driven degradation.
Greener synthesis considerations (for those preparing derivatives):
Employ Baker–Venkataraman or Algar–Flynn–Oyamada routes under catalytic, solvent‑minimized conditions; explore solid‑state or microwave methods to reduce time/solvent.
Replace halogenated solvents with alcohols, esters, or green ethers where compatible; use heterogeneous bases (K2CO3) and recyclable catalysts.
Note: Validate that greener conditions do not compromise spectral integrity or purity. Item-specific green certifications are not provided for this SKU.
Pharmaceutical Uses
No pharmacopeial status, excipient role, or GMP grade is specified for this SKU; refer to the CoA/Spec Sheet for any regulatory information. The content below concerns general laboratory and formulation context only and makes no therapeutic claims.
Typical laboratory/formulation context (general):
Used as a fluorescent analytical marker in in vitro studies of microenvironment polarity and binding interactions.
Can serve as a surrogate standard or internal standard for certain flavonol analyses, provided assay validation supports its use.
Polyphenolic nature may limit stability in strongly basic or oxidative formulation environments; antioxidants and light protection can be considered for analytical solutions.
Regulatory considerations:
Research-use-only materials are not intended for human or veterinary applications, clinical diagnostics, or as APIs/excipients in marketed products.
If adapting for process development analytics, ensure appropriate purity documentation (HPLC/qNMR) and stability data for the intended analytical method.
Handling in development labs:
Prepare fresh standards; verify absence of particulate matter before HPLC/LC–MS injection to protect instrumentation.
Record solvent lots and grades for traceability, especially for fluorescence-based quantitation where background matters.
Conclusion: While valuable as an analytical/fluid‑environment probe in research workflows, no pharmaceutical use is claimed or specified for this item.
Physical Properties
Item-specific physicochemical specifications (e.g., melting point, water content, residual solvents) are not provided in the Product Data for this SKU. Always consult the CoA/Spec Sheet for certified values.
General/literature properties for 3,6,4'-trihydroxyflavone (reference only; not item specifications):
Phase/appearance: Typically a yellow to yellow‑orange crystalline solid (literature; actual item appearance not specified for this SKU).
Acid–base: Weakly acidic due to three phenolic OH groups; stepwise pKa values for related 3‑hydroxyflavones often fall in the ~6–10 range depending on substitution and solvent (literature, qualitative guidance).
Solubility profile: Sparingly soluble in water at neutral pH; soluble in polar aprotic organics (DMSO, DMF) and in alcohols (MeOH, EtOH). Solubility increases in basic aqueous media due to phenolate formation (literature).
Partitioning: Polyphenolic and moderately conjugated; logP for 3‑hydroxyflavones is commonly in the 2–3 range (literature; exact value depends on substitution and measurement method).
UV–vis: Strong π–π* absorption typical of flavonols in the near‑UV with band I/II transitions; exhibits dual fluorescence (N* and T* bands) via ESIPT under appropriate conditions (literature qualitative note).
Stability considerations: Phenolic antioxidants are generally stable in the solid state when kept dry and protected from light. In solution, gradual oxidation and photochemical changes can occur, accelerated by light, oxygen, and alkaline pH (literature).
Not specified for this item; refer to CoA/Spec Sheet for: melting point, exact solubility limits, water content, heavy metals, UV cutoff, and any chromatographic purity metrics.
Quality and Grades
Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet for assay, impurity profile, and any stabilizers.
Context and guidance (general; not item-specific):
Common research grades you may encounter for small organic chromophores include:
Research grade: Suitable for general synthesis and spectroscopy. Purity typically ≥95% by HPLC/GC/NMR, but exact spec varies by supplier.
HPLC/Fluorescence grade: Emphasizes low UV background and minimal fluorescent impurities; useful for analytical or bioimaging applications. UV absorbance specs and residual solvent limits are commonly provided.
Reference standard grade: Provided with detailed characterization package (HPLC/UPLC chromatograms, qNMR, HRMS) suitable for quantitative analytical use.
Stabilizers/antioxidants: Polyphenolic flavonols can auto‑oxidize in solution. Some lots may be packed under inert gas or include oxygen absorbers. If a stabilizer is used, it will be declared on the CoA/Spec Sheet.
Batch-to-batch considerations for flavonols:
Isomeric or O‑methylated impurities can modestly shift UV–vis/fluorescence spectra.
Trace metal ions may influence fluorescence via quenching/chelation; high-purity, low‑metal grades are preferred for spectroscopic work.
Recommendation: If you require low-background fluorescence or tight impurity control for mechanistic ESIPT studies, request HPLC chromatograms, UV–vis baseline data, and any residual metal analyses for the specific lot.
Reaction and Applications
Applications (general/literature; expand your use cases as appropriate):
Photophysics/ESIPT probe:
3,6,4'-Trihydroxyflavone is a 3‑hydroxyflavone derivative exhibiting excited‑state intramolecular proton transfer, leading to characteristic dual fluorescence (normal N* and tautomer T* bands). It is widely used to probe microenvironment polarity and hydrogen‑bonding dynamics in solutions, micelles, membranes, polymers, and protein binding sites.
Ratiometric fluorescence (I_T*/I_N*) offers internal calibration for environment sensing, minimizing artifacts from concentration or light path.
Analytical/supramolecular:
Phenolic and carbonyl sites enable metal ion coordination; spectral shifts or quenching can report on complexation in analytical assays (literature: Al3+, Zn2+, Fe3+ commonly studied with flavonols).
Noncovalent interactions with cyclodextrins or surfactants are used to modulate solubility and emission.
Synthetic derivatization platform:
The three phenolic OH groups allow selective protection (benzylation, silylation), etherification, and esterification to tailor photophysical properties or attach linkers for conjugation (e.g., to polymers or biomolecules for in vitro studies).
Practical tips (general):
Dry solvents and exclude oxygen/light during photophysical measurements to minimize oxidative quenching and photobleaching.
For ratiometric assays, calibrate in the same solvent system and temperature; define excitation/emission bands to avoid spectral overlap.
When derivatizing, control regioselectivity via protecting-group strategies (e.g., silyl protection at 3‑OH to preserve ESIPT capacity during further functionalization).
Manufacturer Applications: Not specified in Product Data for this SKU. The above reflects common research uses of this chemical class.
Reaction Conditions
No item-specific reaction condition recommendations are provided in the Product Data. The following summarizes general literature conditions for common manipulations of 3‑hydroxyflavones and related polyphenols; adapt to your substrate and safety requirements.
Algar–Flynn–Oyamada oxidation: Chalcone + H2O2/base gives flavonol; greener variants employ catalytic systems or flow.
Spectroscopy sample prep:
Solvents: Spectroscopic grade MeCN, EtOH, or DMSO. Concentrations: 1–10 µM for fluorescence; 10–50 µM for UV–vis.
Light/oxygen control: Use amber glassware; deoxygenate if monitoring long‑lived excited states.
All conditions above are literature guidance and not specifications for this item.
Safety and Handling
Item-specific hazard classification is not provided in the Product Data for this SKU (no signal word, H‑statements, GHS classes, or pictograms listed). Always consult the product SDS for authoritative safety information.
General laboratory safety guidance for polyphenolic flavonols (literature/practice, not item-specific):
Expected hazards: Low volatility solid; may cause irritation to eyes, skin, or respiratory tract if dust is generated. Avoid inhalation and contact. Phenolic compounds can be harmful if swallowed in significant quantities.
PPE: Use lab coat, safety glasses or goggles, and appropriate chemically resistant gloves (e.g., nitrile). Handle powders in a fume hood or ventilated enclosure to minimize dust.
Storage incompatibilities: Avoid strong oxidizers (can promote phenolic oxidation), strong bases (can accelerate degradation/air oxidation in solution), and strong acids for prolonged periods. Protect from light to limit photodegradation of conjugated chromophores.
Handling tips: Prepare solutions freshly or store aliquots under inert atmosphere (e.g., argon) in amber vials at low temperature when feasible. Minimize repeated freeze–thaw of solutions.
First aid overview (consult SDS for details):
Eye/skin contact: Rinse cautiously with water for several minutes; remove contaminated clothing. Seek medical attention if irritation persists.
Inhalation: Move to fresh air; seek medical advice if symptoms occur.
Ingestion: Rinse mouth; seek medical attention.
Fire safety: Organic solid; combustible. Use CO2, dry chemical, or foam for small fires. Avoid water jets that may spread material.
Note: This product is for research use only and not for human or animal consumption or diagnostic use.
Solvent Selection
As a polyphenolic, moderately conjugated flavonol, 3,6,4'-trihydroxyflavone dissolves best in polar organic solvents and exhibits solvent‑dependent spectroscopic behavior.
Practical stock solvents (literature/practice):
DMSO or DMF: Excellent solvating power for phenolic aromatics; ideal for concentrated stocks (e.g., 10–50 mM). Hygroscopic—use anhydrous grades to maximize stability.
Alcohols (MeOH, EtOH): Good solubility; facile for UV–vis/fluorescence measurements. Avoid prolonged storage in basic alcohols.
MeOH/EtOH: Convenient, but may alter emission profiles via H‑bonding.
MeCN: Balanced; low background for spectroscopy; moderate solubility.
Note: For chromatography or analytical fluorescence, select solvent grades with low UV absorbance and minimal fluorescent impurities. Item-specific solvent compatibility limits are not specified for this SKU; consult CoA/Spec Sheet if needed.
Storage and Reconstitution
Item-specific storage: Room temperature (per Product Data). If long-term storage is anticipated, protecting from light and moisture is recommended for polyphenolic chromophores.
Packaging and shipping: Not specified for this item; refer to CoA/Spec Sheet. As a low‑volatility solid, it is typically shipped at ambient conditions unless otherwise noted.
Reconstitution/preparation (general guidance):
Solvents: DMSO, DMF, methanol, ethanol, or acetonitrile. Begin with small volumes and sonicate gently if needed. Water solubility at neutral pH is low; use cosolvent strategies for aqueous media.
Concentrated stocks: 1–50 mM in anhydrous DMSO or ethanol. Filter through 0.2 µm PTFE for spectroscopic clarity.
Aliquoting: Dispense into amber vials under inert gas (optional) to minimize oxidation; store tightly capped.
Short- and long-term stability (general):
Solid: Stable when dry, protected from light, and at ambient temperature; desiccation reduces moisture uptake.
Solution: More susceptible to oxidation and photodegradation, especially in basic media and under light. Store solutions at 2–8 °C or −20 °C in amber vials; avoid repeated freeze–thaw cycles.
Disclaimers:
Exact shelf life, assay stability, and impurity limits are not specified for this item; consult the lot-specific CoA/Spec Sheet.
For research use only. Not for human or animal use.
Structure and Identity
Brief overview: 3,6,4'-Trihydroxyflavone is a polyphenolic flavonol (a 3‑hydroxyflavone) bearing phenolic OH groups at the 3-position of the heterocycle, the 6-position of the A-ring, and the 4'‑position of the B‑ring. It is widely used as an ESIPT (excited‑state intramolecular proton transfer) fluorescent reporter in physical organic and biophysical studies.
Product Data (item-specific):
SKU: T1006868
Product name: 3,6,4'-Trihydroxyflavone
Storage: Room temperature (per Product Data)
Research use: For research use only
Other identifiers (SMILES, InChI/InChIKey, CAS-related specs): Not specified for this item; refer to CoA/Spec Sheet.
Literature identity (for reference; not item specifications):
Core scaffold: Flavone (1-benzopyran-4-one) with an additional OH at C-3 (thus a flavonol)
Functional groups: One conjugated aryl ketone (lactone-like chromone carbonyl), one aryl–O–aryl ether within the chromone ring system, and three phenolic OH groups (3, 6, 4').
Structural description in words (general):
A bicyclic chromone (benzopyran-4-one) ring fused to a benzene A-ring, with a pendant para‑hydroxyphenyl B‑ring at C-2.
The 3‑OH participates in strong intramolecular hydrogen bonding to the 4‑one carbonyl, enabling ESIPT behavior.
Substitution pattern: 6‑OH on the chromone A‑ring; 4'‑OH on the para position of the phenyl B‑ring.
Note: Where precise identifiers (SMILES, InChIKey) are required for informatics, consult the CoA/Spec Sheet or contact Aladdin Scientific for the exact registry data corresponding to this SKU.
Synthetic Utility
From a synthetic perspective, 3,6,4'-trihydroxyflavone is both a versatile polyphenolic scaffold and a photophysically rich core for probe derivatization.
Functional group handles:
Three phenolic OH groups (3, 6, 4') enable selective protection and diversification (O‑alkylation, O‑acylation, carbonate/urethane formation). Regioselectivity can be steered via protecting groups (e.g., silyl or benzyl) and choice of base/solvent.
The chromone carbonyl engages in hydrogen bonding and can participate in condensation or acyl transfer under activating conditions.
Typical transformations (literature):
O‑alkylation: K2CO3 or Cs2CO3 in DMF/acetone with alkyl halides or tosylates affords anisole-like ethers. Phase-transfer catalysis can improve selectivity.
O‑acylation: Ac2O or acyl chlorides in pyridine/DMAP deliver esters for tuning lipophilicity and emission.
Electrophilic aromatic substitution on the B‑ring is limited by deactivation; prefunctionalized analogs are more amenable to cross‑coupling. However, late-stage demethylation (BBr3) of protected methoxy precursors is common.
Metal complexation: Formation of chelates via 3‑OH/4‑carbonyl can be leveraged to build coordination probes (release/transfer ligands in situ).
Retrosynthetic access (general routes):
Baker–Venkataraman rearrangement of 2‑acylated phenyl benzoates, followed by cyclodehydration and oxidative steps to introduce the 3‑OH (flavonol formation).
Algar–Flynn–Oyamada oxidation of chalcones to flavonols using H2O2/base or catalytic variants; substituent placement (6‑OH, 4'‑OH) is controlled by starting phenols.
Guidance: Maintain ESIPT capability by preserving a free 3‑OH and the 4‑one; protect selectively during multistep sequences to retain desired photophysics.
Target Specificity
Not applicable. This product is a small-molecule flavonol, not an antibody, enzyme, or biological that exhibits defined antigen/epitope specificity. No target binding specificity is provided in the Product Data.
We use cookies to ensure the website functions properly and, where permitted, to improve your experience. You can manage your preferences at any time in Settings. Learn more in our Cookie Policy.
Shall we send you a message when we have discounts available?
Remind me later
Thank you! Please check your email inbox to confirm.
Products are supplied to verified businesses, institutions, and qualified professionals for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
