3-Hydroxy-4',7,8-trimethoxyflavone , CAS No.57499-06-6

CAS: 57499-06-6 Cat. No.: H992963 Summenformel: C₁₈H₁₆O₆ Molekulargewicht: 328.300 EG-Nummer: 676-571-0

Storage

Room temperature

Specifications

Storage

Room temperature

Namen und Kennungen

• Kanonisches Lächeln: COC1=CC=C(C=C1)C2=C(C(=O)C3=C(O2)C(=C(C=C3)OC)OC)O
• IUPAC Name: 3-hydroxy-7,8-dimethoxy-2-(4-methoxyphenyl)chromen-4-one
• InChIKey: XTFPORCSCKBAHV-UHFFFAOYSA-N
• INCHI: 1S/C18H16O6/c1-21-11-6-4-10(5-7-11)16-15(20)14(19)12-8-9-13(22-2)18(23-3)17(12)24-16/h4-9,20H,1-3H3
• Molekulargewicht: 328.300

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Klasse Flavonoids
      • Subclass Flavones

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Klasse: Flavonoids
• Subclass: Flavones
• Intermediate Tree Nodes: Not available
• Direct Parent: Flavonols
• Alternative Parents: 8-O-methylated flavonoids 7-O-methylated flavonoids 4'-O-methylated flavonoids 3-hydroxyflavonoids Chromones Phenoxy compounds Methoxybenzenes Anisoles Pyranones and derivatives Alkyl aryl ethers Heteroaromatic compounds Oxacyclic compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: 4p-methoxyflavonoid-skeleton - 7-methoxyflavonoid-skeleton - 3-hydroxyflavone - 8-methoxyflavonoid-skeleton - 3-hydroxyflavonoid - Hydroxyflavonoid - Chromone - Benzopyran - 1-benzopyran - Phenoxy compound - Phenol ether - Methoxybenzene - Anisole - Pyranone - Alkyl aryl ether - Pyran - Monocyclic benzene moiety - Benzenoid - Heteroaromatic compound - Ether - Organoheterocyclic compound - Oxacycle - Organic oxygen compound - Organooxygen compound - Hydrocarbon derivative - Organic oxide - Aromatic heteropolycyclic compound
• Beschreibung: 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: Flavones and Flavonols

Data sources

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.

DOI: 10.1186/s13321-016-0174-y

Chemische und physikalische Eigenschaften

• Molekulargewicht: 328.300 g/mol
• XLogP3: 2.900
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 328.095 Da
• Monoisotopic Mass: 328.095 Da
• Topological Polar Surface Area: 74.200 Ų
• Heavy Atom Count: 24
• Formal Charge: 0
• Complexity: 494.000
• 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

Application Protocols

No manufacturer-validated protocols are provided for this item. General laboratory practices for small-molecule handling apply:

• Stock preparation (general)

  • Dissolve in anhydrous DMSO to 10–50 mM; vortex and, if needed, briefly sonicate. Filter through 0.2 µm PTFE for spectroscopy.
  • For alcohol or acetonitrile stocks, warm gently (≤40 °C) to aid dissolution and cool before use.

• Use in spectroscopic assays (general)

  • Work at 1–10 µM in optically transparent solvents; protect from strong light; equilibrate temperature to ensure reproducibility of ESIPT features.

• Metal-binding studies (general)

  • Titrate aqueous/MeOH buffer solutions with metal salts; maintain pH to keep ligand deprotonation/complexation consistent; record UV–Vis/fluorescence changes.

These are literature-style suggestions and are not product certifications.

Biological Roles

• General biochemistry context (no clinical claims)

  • Flavonols like 3-hydroxyflavone derivatives are plant secondary metabolites associated with UV protection, pigmentation, and stress responses. Methoxy substitution modulates membrane permeability and metabolic stability.
  • The 3-hydroxy–4-keto motif supports metal chelation; binding to Fe3+/Cu2+/Al3+ can alter redox behavior and spectroscopic signatures.
  • As phenolic ethers, O-demethylation by cytochrome P450s is a common metabolic route in vitro; conjugation (glucuronidation/sulfation) often follows phenolic liberation.
  • Antioxidant and radical-scavenging capacity generally correlate with free phenolic positions and substitution pattern; methoxy groups can influence electron density and H-atom transfer kinetics.

• Laboratory relevance

  • Used as a model scaffold to study ESIPT fluorescence in microenvironments (proteins, membranes, micelles).
  • Serves as a probe for examining phase partitioning and binding to serum albumin/transport proteins via steady-state and time-resolved spectroscopy.

Note: These points describe general roles of methoxylated 3-hydroxyflavones in biochemical research and are not product-specific potency or efficacy claims.

Buffer Applications

This reagent is not a buffering agent and is not typically used to prepare buffer systems. For biological assays, it is commonly dissolved as a DMSO stock and then diluted into an existing buffer (e.g., PBS, HEPES) with a low final DMSO percentage to prevent precipitation. Adjust the buffer composition (pH, protein content, surfactant) to maintain solubility and avoid nonspecific adsorption when working at sub-micromolar concentrations.

Green Alternatives

While the substance itself is a solid reagent, its handling and transformations often involve organic solvents. Greener choices can reduce environmental impact without compromising performance.

• Greener dissolution media (general)

  • Ethanol (bio-derived) or isopropanol can replace acetonitrile or dichloromethane for many spectroscopy and extraction tasks, acknowledging possible solubility differences.
  • 2-Methyltetrahydrofuran (2-MeTHF) or cyclopentyl methyl ether (CPME) may substitute for THF/Et2O in some derivatizations; check solubility and reaction rates.
  • Ethyl acetate often substitutes for chlorinated solvents in workups and chromatography.

• Emerging options

  • Deep eutectic solvents (choline chloride–glycerol, etc.) have been reported for polyphenol extraction and modification; evaluate viscosity and compatibility with downstream analytics.
  • Aqueous micellar catalysis (TPGS-750-M) can enable O-acylations/alkylations under milder, water-rich conditions.

• Trade-offs

  • Solubility vs sustainability: Highly polar aprotics (DMSO/DMF) dissolve flavonols well but are harder to remove and have higher EHS burdens. Alcohols/esters are greener but may require heating or co-solvents.
  • Photophysics: Solvent polarity/hydrogen bonding affects ESIPT behavior; when swapping solvents, re-establish calibration curves.

• Quick comparison (general)

  • ACN: fast evaporation, petro-derived; EtOH: renewable, safer, slower evaporation.
  • DCM: excellent for Lewis-acid steps but chlorinated; EtOAc: greener, broader safety margin.

Pharmaceutical Uses

• Item-specific regulatory status: Not specified for this item; refer to CoA/Spec Sheet.

• General roles for related compounds (no therapeutic claims)

  • Analytical/quality control: Methoxylated flavonols can serve as reference standards for assay calibration in natural product analysis and stability-indicating methods.
  • Preformulation research: Used to study solubilization strategies (co-solvents, cyclodextrins, amorphous dispersions) for poorly water-soluble polyphenolics.
  • Excipient interactions: Investigations into binding with cellulose derivatives, PVP, or cyclodextrins to modulate dissolution and photostability.

• Practical notes

  • For dosage-form research, define polymorph/amorphous state and moisture uptake as they influence dissolution.
  • Document residual solvent limits and elemental impurities if developing internal standards; follow ICH Q3 guidelines as applicable within a research framework.

Physical Properties

• Item-specific specifications

  • Appearance: 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.

• Literature/general expectations for this class (3-hydroxyflavones; informational only, not product specifications)

  • Physical state: Typically a yellow to off-yellow crystalline solid for conjugated flavones/flavonols.
  • Melting point: Often in the 200–300 °C range for poly-methoxylated flavonols (varies with substitution).
  • Solubility profile: Poorly soluble in water; soluble in polar aprotic and polar protic organic solvents (DMSO, DMF, acetone, methanol, ethanol); enhanced solubility in hot alcohols and with co-solvents or cyclodextrins.
  • UV–Vis: Strong π–π* transitions for flavone backbone (typical bands I/II in 250–380 nm region), red-shifted/strengthened with 3-OH and methoxy substitution (qualitative note).
  • Acid–base: Phenolic 3-OH is weakly acidic (flavonol pKa typically ~6–9 depending on substitution); keto–enol tautomerization contributes to spectral properties.
  • LogP: Methoxy substitution generally yields moderate lipophilicity (often logP ~2–3.5 for trimethoxyflavonols; literature ranges).

Note: For exact specifications of this item (mp, purity, UV cutoff, water content, residual solvents, metals), consult the item’s CoA/Specification Sheet.

Quality and Grades

• Item-specific quality information

  • Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
  • Stabilizers/Additives: Not specified for this item; refer to CoA/Spec Sheet.

• How to interpret grades for this compound class (general guidance)

  • Research/analytical grade flavonoids are typically qualified by HPLC purity (% area), identity by NMR/HRMS, and water/volatile content by KF/LOD. If designated as reference-standard grade, additional orthogonal assays (qNMR) and impurity profiling may be provided.
  • Low-UV-absorbing solvent residuals and defined moisture content are important for spectroscopic/biochemical assays due to the strong intrinsic UV absorbance of flavones.

• Practical considerations

  • For quantitative work (calibration standards, SAR, photophysics), request the latest CoA with HPLC trace, assay basis, and residual solvent profile.
  • If your application is moisture/oxygen sensitive (e.g., metal complexation studies), confirm water content and consider brief vacuum drying before use.
  • Batch-to-batch comparability: Retain a reference spectrum (1H/13C NMR, UV–Vis) for internal QC.

Reaction and Applications

• Typical research uses (general; expand from compound class)

  • Chemical biology probes: Flavonols are used to interrogate oxidative stress chemistry, metal chelation, and fluorescence-based sensing (3-hydroxy–4-keto motif can chelate Al3+, Zn2+, Fe3+).
  • Photophysics: 3-hydroxyflavones exhibit excited-state intramolecular proton transfer (ESIPT), enabling ratiometric fluorescence; methoxy substitution modulates emission.
  • Reference material: Useful as a standard in plant metabolomics/polyphenol profiling and for structure–activity relationship (SAR) sets involving methoxy patterns.

• Synthetic/derivatization applications (see also Synthetic Utility)

  • O-Functionalization: 3-OH permits ether/ester formation (alkylation/acylation) to tune solubility or photophysical behavior.
  • Demethylation: BBr3 or AlCl3/thiols can selectively remove aryl OMe groups to access catechol-like motifs for further coupling/complexation.
  • Metal complexes: Formation of chelates (e.g., Al3+) used to study shifts in UV–Vis/fluorescence or to construct coordination materials.

• Practical tips

  • Drying: Brief vacuum drying at ambient temperature protects against hydrate-associated spectral variability.
  • Light sensitivity: Store and handle under subdued light to limit photochemical changes.
  • Stock solutions: Filter (0.2 µm PTFE) DMSO or ACN solutions for reproducible spectroscopic baselines.

Note: No manufacturer-specific application notes were provided for this item; above reflects literature-guided practices for 3-hydroxyflavone derivatives.

Reaction Conditions

General literature guidance for derivatization of 3-hydroxyflavone scaffolds (non-product-specific):

• O-Alkylation at 3-OH

  • Typical: 1.1–1.5 equiv alkyl halide, 1.5–2.0 equiv K2CO3 or Cs2CO3, DMF or acetone, 25–60 °C, 2–16 h. Yields often 60–90% depending on sterics and leaving group.
  • Tips: Dry solvent, exclude moisture. For hindered alkylation, use NaH (carefully) in THF or DMF at 0–25 °C.

• O-Acylation/Carbamate

  • Acyl chloride (1.1–1.5 equiv), pyridine or triethylamine base, catalytic DMAP, DCM or ACN, 0–25 °C, 1–4 h.

• Demethylation of aryl OMe

  • BBr3 (1–3 equiv per OMe), DCM, −78 to 0 °C, 1–6 h; quench with MeOH/H2O. Sequential additions may afford selectivity across 7/8/4' positions. Alternative: BCl3 with TBAI or AlCl3/thiophenol under refluxing toluene.

• Metal complex formation

  • Mix flavonol (1.0 equiv) with metal salt (e.g., AlCl3, Zn(OAc)2, FeCl3, 0.5–1.0 equiv) in MeOH/EtOH or MeCN with base (Et3N) to adjust pH ~7–8; monitor by UV–Vis/fluorescence.

• Photophysical assays (ESIPT)

  • Solvent: dry MeOH/ACN/EtOH; c ~1–10 µM. Excite near band I (typically 340–380 nm); record dual emission (N* vs T* forms). Avoid oxygen quenching for time-resolved studies.

These conditions are representative literature practices and should be optimized for your specific substitution pattern and scale.

Safety and Handling

• Product-specific hazard data (from Product Data)

  • GHS classification: Not specified for this item; refer to SDS.
  • Signal word / H-statements / pictograms: Not specified for this item; refer to SDS.

• General laboratory safety for polyphenolic flavonoids (informational only)

  • Likely low volatility solid; avoid dust formation and inhalation. Handle in a fume hood when weighing.
  • Personal protective equipment: Safety glasses, lab coat, and appropriate gloves (e.g., nitrile). Avoid skin/eye contact.
  • Incompatibilities: Strong oxidizers; strong bases/acids may promote degradation or O-demethylation under forcing conditions. Protect from strong UV light to minimize photodegradation.
  • First aid (overview; defer to SDS): If inhaled, move to fresh air; if on skin/eyes, rinse with water for ≥15 min; if ingested, rinse mouth and seek medical advice. Provide SDS to medical personnel.
  • Spill/cleanup: Avoid raising dust; gently sweep/HEPA vacuum and place in suitable container for disposal per institutional and local regulations.
  • Waste: Dispose as organic laboratory waste in accordance with regulations.

Always consult the product-specific Safety Data Sheet (SDS) for authoritative hazard, toxicological, and regulatory information.

Solvent Selection

This compound is an aromatic polyphenolic ether (trimethoxy-substituted flavonol) with low aqueous solubility and good solubility in polar organics.

• Miscibility/solubility tendencies (literature/general)

  • Water: Poorly soluble.
  • DMSO, DMF, NMP: High solubility; ideal for stock solutions.
  • Alcohols (MeOH, EtOH, i-PrOH): Moderate to good solubility; heat can aid dissolution.
  • Acetone, acetonitrile, ethyl acetate: Typically soluble to moderately soluble.
  • Nonpolar (hexanes, toluene): Limited solubility; toluene may dissolve upon heating due to π–π interactions.

• Choosing a medium

  • Biological assays: Prepare concentrated DMSO stocks (e.g., 10–50 mM), then dilute into aqueous buffers with ≤1% DMSO final to avoid precipitation.
  • Spectroscopy/photophysics: Use dry MeOH/EtOH/ACN for resolved UV–Vis/fluorescence spectra; note solvatochromic shifts.
  • Synthesis/derivatization: DMF/DMSO/acetone commonly used for O-alkylation/acylation; dichloromethane or toluene for Lewis acid-mediated steps.

• Small comparison (general)

  • DMSO vs DMF: DMSO offers highest solubility but can reduce some metals; DMF is less viscous and easier to remove.
  • MeOH/EtOH: Greener and volatile; may participate in acyl/alkyl transfer under basic conditions.

Storage and Reconstitution

• Item-specific storage

  • Storage conditions: Room temperature (as provided). Store tightly closed in a dry place.
  • Shipped in: Not specified for this item; refer to CoA/Spec Sheet.

• General best practices for this class of compounds

  • Protect from light: Use amber vials/foil wrapping to minimize photodegradation.
  • Moisture control: Keep desiccated; avoid prolonged exposure to humid air which can affect spectral properties and weight accuracy.
  • Long-term stability: For multi-month storage, consider 2–8 °C in the dark for added margin, allowing equilibration to room temperature before opening to prevent condensation.

• Reconstitution (general guidance)

  • Prepare concentrated stock solutions in DMSO (e.g., 10–50 mM) or in MeOH/EtOH as needed. If precipitation occurs upon aqueous dilution, increase co-solvent fraction or add surfactant/protein carrier as appropriate to the assay.
  • Avoid repeated freeze–thaw of solutions; aliquot stocks and store at −20 °C (DMSO or alcohol) protected from light. Thaw at ambient temperature and mix thoroughly before use.

• Research use note

  • For research use only. Not for human or veterinary use.

Structure and Identity

Brief overview: 3-Hydroxy-4',7,8-trimethoxyflavone is a trimethoxy-substituted flavonol (a 3-hydroxyflavone) bearing methoxy groups at the 4' position of the B-ring and at the 7 and 8 positions of the A-ring.

• Item-specific identifiers (from Product Data)

  • SKU: H992963
  • Product name: 3-Hydroxy-4',7,8-trimethoxyflavone
  • CAS: 57499-06-6
  • PubChem CID: 42553051
  • InChIKey: 426663 (as provided)
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/computed identity details (non-specification)

  • Compound class: Flavonol (3-hydroxyflavone derivative)
  • Typical ring system: 1 benzopyran-4-one (chromen-4-one) fused to a phenyl (B-ring)
  • Substitution pattern: 3-OH on the heterocycle (C-ring); 7-OMe and 8-OMe on A-ring; 4'-OMe on B-ring
  • Approximate formula and molecular weight (computed from the name; not item specification): C18H16O6, MW ≈ 328.32 g/mol

• Structural description in words (general)

  • The scaffold is a planar, conjugated chromen-4-one core. The 3-hydroxyl and 4-keto functions form a classical 3-hydroxy-4-keto chelating motif. Three methoxy substituents increase lipophilicity and modulate electronics (two ortho methoxys at 7/8 on A-ring, one para methoxy on B-ring). No stereogenic centers are present.

Synthetic Utility

• Functional groups and reactivity (general)

  • 3-Hydroxyl with adjacent 4-keto enables chelation and ESIPT; acts as a nucleophile under basic conditions for O-alkylation/acylation.
  • Three anisole-type methoxy groups are directing/electron-donating; they can be demethylated (BBr3, BCl3/TBAI) to reveal phenols, enabling further cross-couplings (via subsequent halogenation) or ether/ester formation.
  • The conjugated enone in the chromen-4-one ring is electrophilic; careful with strong nucleophiles to avoid ring opening or 1,4-addition side reactions.

• Transformations

  • O-Alkylation: K2CO3 or Cs2CO3 in DMF/acetone with alkyl halides to give 3-alkoxyflavones.
  • O-Acylation/Carbamate formation: Acyl chlorides/activated carbonates with base in DCM or ACN; DMAP catalysis enhances rates.
  • Demethylation: BBr3 in DCM at −78 to 0 °C affords phenols; stepwise selectivity possible due to differential activation.
  • Metal coordination: Generation of stable Al3+/Zn2+ complexes for materials/photophysical studies.

• Retrosynthetic value

  • Serves as a late-stage diversification node in flavone libraries—orthogonal handles (3-OH vs aryl OMe) allow tuning of polarity and chromophore properties without altering the core scaffold.

Target Specificity

Not applicable. This product is a small-molecule flavonol, not an antibody, enzyme, or nucleic acid reagent. No target specificity data (antigen, epitope, clone, isotype, species reactivity) are provided for this item.