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
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.
Zertifikate (CoA, COO, BSE/TSE und Analyse-Diagramm)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Chemische und physikalische Eigenschaften
Molekulargewicht
252.260 g/mol
XLogP3
3.800
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
1
Exact Mass
252.079 Da
Monoisotopic Mass
252.079 Da
Topological Polar Surface Area
46.500 Ų
Heavy Atom Count
19
Formal Charge
0
Complexity
393.000
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
Lösungsrechner
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Application Protocols
Item-specific tested applications and recommended conditions: Not specified for this item; no validated protocols are provided in the Product Data.
Please refer to domain literature for protocol development relevant to your use case (e.g., fluorescence spectroscopy of ESIPT dyes, HPLC reference standard preparation, or derivatization reactions). Any procedure should be validated in your laboratory setting with appropriate controls.
Biological Roles
General biochemistry context (literature)
Flavonols (3‑hydroxyflavones) are a subclass of flavonoids found broadly in plants where they participate in UV protection, pigmentation, and interactions with proteins and metal ions. They display characteristic redox and H‑bonding behavior and can act as antioxidants in model chemical systems.
6‑Methylflavonol is a synthetic or rare natural analogue featuring a methyl group that modulates hydrophobicity and electronic distribution on the A‑ring. This substitution can influence membrane partitioning in model systems and alter binding affinities in biophysical assays.
Research applications (non-clinical)
Used as a fluorescent reporter for microenvironment polarity and H‑bond donor/acceptor capacity via ESIPT dual emission. Ratios of tautomer/normal bands provide sensitive readouts that have been applied to study protein binding pockets, micelles, and lipid bilayers.
Chelation: the 3‑hydroxy‑4‑keto motif binds metal ions in vitro, altering spectral signatures; such responses can be exploited to probe metal availability or site interactions in biochemical models.
Metabolism/transformations (general)
Phenolic flavonoids can undergo phase II conjugation (glucuronidation, sulfation) in biological systems; methyl substitution at C‑6 may modulate metabolic rate and regioselectivity in comparative studies (literature trends).
Note: All uses are for research and laboratory investigations only. No medical, diagnostic, or therapeutic claims are made.
Buffer Applications
This compound is not a buffer reagent and is not typically used to set or maintain solution pH.
Applicability
Not typically applicable as a buffering component.
Practical note for assays (general guidance)
When used in biochemical assays, prepare a concentrated stock in DMSO or ethanol and dilute into the target buffer (e.g., phosphate, HEPES) keeping organic cosolvent ≤1% v/v to limit precipitation and solvent effects on biology and photophysics. Adjust pH to control the phenolate/neutral ratio if studying pH‑dependent properties.
For exact preparation instructions specific to this item, refer to your protocol or consult the literature; item-specific buffer recipes are not provided.
Green Alternatives
Because 6‑methylflavonol is a solid research chemical rather than a process solvent, “green alternatives” primarily concern solvent selection and processing choices during its use and derivatization.
Greener solvent choices (general guidance)
Prefer ethanol or isopropanol over chlorinated solvents for dissolution and crystallization when solubility allows.
For reactions, consider 2‑MeTHF or CPME as ether alternatives to THF; ethyl acetate can replace DCM for many workups and chromatographic mobile phases (with heptane/IPA systems).
Water/ethanol cosolvent systems can support spectroscopy and some biophysical assays, minimizing DMSO content.
Environmental/health tradeoffs (general)
DMSO: low toxicity profile but persistent; excellent solubilizer.
Acetonitrile: good UV transparency, but toxic flammability risk and waste burden.
Ethanol: renewable and low toxicity; may alter ESIPT behavior via H‑bonding compared with aprotics.
Small comparison table (general; not item specifications)
Use case: stock solutions — DMSO (high solubility) vs ethanol (greener, lower solubility).
Use case: O‑alkylation — DMF (effective but problematic) vs MeCN/2‑MeTHF (cleaner EHS profile, may require optimization).
Use case: chromatography — heptane/EtOAc or heptane/IPA over hexane/DCM to reduce chlorinated solvent usage.
Recommendation: Select the least hazardous solvent that maintains required solubility and performance, validate photophysical properties in the chosen greener medium, and document any shifts induced by solvent polarity/H‑bonding.
Pharmaceutical Uses
Item-specific regulatory status
Pharmacopeial status (USP/Ph.Eur./JP): Not specified for this item; refer to CoA/Spec Sheet.
Typical roles in pharmaceutical R&D (general; not therapeutic claims)
Reference standard: Flavonoids and their analogues are commonly employed as analytical reference materials for method development and system suitability in HPLC‑UV/FLD.
Discovery chemistry scaffold: The flavonol core is a versatile heteroaromatic pharmacophore used in SAR studies; 6‑methyl substitution offers a hydrophobic/electronic handle for tuning in vitro properties.
Excipient use: No common role as an excipient.
Formulation considerations (general guidance)
Low aqueous solubility suggests use of cosolvents (ethanol, PG), surfactants, or solid dispersion approaches for exploratory in vitro dosing. Control of pH influences ionization (phenolate formation) but may alter photophysics and stability.
Note: This product is supplied strictly for research use only. It is not intended for human or veterinary use, clinical applications, or as an active pharmaceutical ingredient.
Physical Properties
Item-specific (from Product Data)
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Storage conditions: Room temperature (as provided).
Other specifications (mp/bp, density, UV cutoff, residuals, metals, water): Not specified for this item; refer to CoA/Spec Sheet.
Literature/general properties (for reference only; not item specifications)
Physical state: typically a crystalline solid for flavonol derivatives of this type.
Solubility profile: sparingly soluble in water; soluble in polar aprotic organics (DMSO, DMF, acetone) and moderately in alcohols (ethanol, methanol), with solubility enhanced by base (phenolate formation) or by cosolvents/surfactants.
Acid–base: 3‑phenolic OH is weakly acidic (flavonol pKa often ~7–9, literature range depends on substitution). Deprotonation increases aqueous solubility and bathochromically shifts UV–Vis spectra (general flavonol behavior).
Spectroscopy: strong π→π* absorption in near‑UV with vibronic structure; ESIPT leads to dual fluorescence bands (normal and tautomer emissions) sensitive to microenvironment polarity and H‑bonding strength (literature for 3‑hydroxyflavones).
Partitioning: methyl substitution generally increases hydrophobicity (higher logP than unsubstituted 3‑hydroxyflavone; qualitative literature expectation).
Notes: Where exact numeric values (mp, logP, UV λmax) are critical, please consult primary literature or request the item-specific CoA/Spec Sheet.
Quality and Grades
Item-specific information
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/Inhibitors: Not specified for this item; refer to CoA/Spec Sheet.
Guidance on grades (general context for this molecule class)
Analytical/reference grade: When 6‑methylflavonol is used as a spectroscopic or chromatographic reference (e.g., fluorescence, UV–Vis, LC), low levels of UV‑active impurities and defined water content are desired; HPLC assay and residual solvent/water are typically reported on the CoA.
Synthesis grade: For use as a building block or probe in organic synthesis or photophysical studies, the key attributes are assay purity, identity confirmation (1H/13C NMR, HRMS), and low inorganic residue (sulfated ash or metals, if relevant).
Impurity considerations: Isomeric flavones/flavonols, unreacted precursors, and O‑methylated byproducts can co‑elute. For fluorescence applications, even trace impurities may perturb emission; verify purity by HPLC with DAD/FLD when necessary.
Stabilizer implications: Flavonols generally do not require stabilizers. If any stabilizer is used to enhance shelf life or suppress oxidative discoloration, it should be disclosed on the CoA; absence/presence is item-specific.
Recommendation: Use the batch CoA to confirm suitability for sensitive analytical work (e.g., quantum yield standards), and document any additional in‑house purification (recrystallization, preparative HPLC) if your application demands ultra‑high purity.
Reaction and Applications
Photophysical probe (literature)
3‑Hydroxyflavones, including 6‑methylflavonol, exhibit ESIPT (excited‑state intramolecular proton transfer) leading to dual fluorescence (normal vs tautomer bands). The 6‑Me group tunes electron density on the A‑ring, shifting emission and affecting sensitivity to H‑bonding and polarity. Applications include microenvironment polarity sensing, hydrogen‑bond donor/acceptor studies, and excited‑state dynamics.
Analytical/standards
Useful as a reference compound in flavonoid analysis (HPLC‑UV/FLD) and as a calibration/check standard for ESIPT fluorophores.
Coordination/chelation studies (literature)
The 3‑hydroxy‑4‑keto motif can chelate metal ions in the deprotonated form, enabling model studies of metal–flavonol interactions (e.g., with Al3+, Fe3+), which often induce bathochromic shifts and fluorescence modulation.
Synthetic transformations (general)
O‑Derivatization: the 3‑OH undergoes O‑alkylation (e.g., with alkyl halides) or O‑acylation (acyl chlorides/anhydrides) under basic or catalytic conditions to give ethers/esters, enabling probe tuning or protecting‑group strategies.
Electrophilic aromatic substitution on the B‑ring (nitration, halogenation) can install handles for cross‑coupling; the 6‑methyl ortho/para-directs on the A‑ring but also blocks positions, influencing regioselectivity.
Cross‑coupling: after halogenation, Suzuki–Miyaura or Sonogashira reactions can expand the conjugation for tailored photophysical properties.
Practical tips
Dry conditions limit base‑promoted side reactions and hydrolysis of acyl derivatives.
Monitor by HPLC‑DAD or TLC under UV (254/365 nm), exploiting the strong chromophore.
For photophysics, rigorously control solvent purity, oxygen content (degassing can reduce quenching), and concentration to avoid inner‑filter effects.
Reaction Conditions
General literature guidance for typical transformations of 3‑hydroxyflavones; adapt to your system and verify experimentally.
O‑Alkylation (to 3‑alkoxy derivatives)
Conditions: K2CO3 (2–3 equiv) in dry DMF or acetonitrile, alkyl halide (1.2–2 equiv), 20–60 °C, 2–16 h. Alternatively, NaH (1.1–1.5 equiv) in THF/DMF at 0–25 °C for more hindered electrophiles. Monitor by TLC/HPLC.
O‑Acylation
Conditions: acyl chloride or anhydride (1.2–2 equiv) with pyridine or Et3N in DCM/MeCN, 0–25 °C; or DMAP-catalyzed Steglich esterification (DCC/EDC) in DCM at 0–25 °C. Typical reaction times 1–6 h.
Mild halogenation: NBS/NCS (1.1 equiv) in acetonitrile or AcOH, 0–25 °C; regioselectivity depends on substitution pattern.
Cross‑coupling (after aryl halide installation)
Suzuki–Miyaura: Pd(PPh3)4 (1–3 mol%), base (K2CO3, K3PO4), dioxane/H2O or MeCN/H2O, 50–90 °C, 4–16 h.
Sonogashira: Pd/Cu co‑catalysis, amine base (Et3N/DIPEA), THF/MeCN, 25–60 °C.
Photophysics measurements (use guidance, not a specification)
Solutions: 1–50 µM in spectroscopic‑grade solvents. Deoxygenation (argon sparge) can reduce quenching. Record excitation near the first intense UV band; observe dual emission (ESIPT) bands whose ratio is solvent/pH dependent.
Notes:
Above conditions are literature‑style generalizations for flavonol scaffolds; optimize for 6‑methyl substitution as electronics/sterics may shift rates/selectivity.
No item-specific performance data or guaranteed yields are provided; consult primary sources and validate on small scale.
Safety and Handling
Item-specific hazard data
GHS classification: Not specified for this item; refer to SDS.
Signal word and H‑statements: Not specified for this item; refer to SDS.
Pictograms: Not specified for this item; refer to SDS.
Research Use: For research use only (as provided).
Storage: Room temperature (as provided).
General laboratory handling (professional guidance; defer to SDS)
PPE: laboratory coat, safety glasses, and appropriate gloves (e.g., nitrile). Avoid inhalation of dust/particulates and contact with skin/eyes.
Engineering controls: use in a fume hood when weighing, dissolving, or transferring powders/solutions to minimize dust and solvent vapor exposure.
Incompatibilities: strong oxidizers and strong bases/acids may alter the phenolic and conjugated ketone functions; avoid reactive acylating/alkylating agents unless intended.
Hygroscopicity/peroxide risk: Flavonols are not peroxide-forming; hygroscopicity is typically low to moderate. Keep container tightly closed to avoid moisture uptake and contamination.
First‑aid overview (consult SDS): rinse eyes/skin thoroughly with water upon contact; if inhaled, move to fresh air; if ingested, rinse mouth and seek medical attention. Provide SDS to responders.
Spill response: avoid dust generation; collect solids with minimal disturbance; absorb solutions with inert material. Dispose according to institutional and local regulations.
Always consult the product‑specific SDS for authoritative hazard classification, exposure limits, and disposal guidance.
Solvent Selection
6‑Methylflavonol is a moderately hydrophobic, conjugated phenolic ketone. Solvent choice should balance solubility, chemical stability (phenol vs base), and spectroscopic transparency if used as a probe.
Polarity/miscibility (general)
Water: very low solubility in neutral water; solubility increases upon deprotonation (basic pH) but may change photophysics.
Polar aprotic: DMSO, DMF, NMP – high solubility; good for stock solutions and synthesis; note DMSO’s own UV cutoff if doing UV–Vis below ~270 nm.
Protic solvents: ethanol, methanol, isopropanol – moderate solubility; suitable for spectroscopy and bioassay cosolvent dosing.
Esters/ketones: ethyl acetate, acetone – useful for workup and recrystallization; acetone can participate in base-promoted reactions, so avoid strong base.
Nonpolar: toluene, dichloromethane – limited solubility; may be useful at elevated temperature or for chromatography.
Practical selection tips
Prepare concentrated stocks in anhydrous DMSO or ethanol (e.g., 10–50 mM), then dilute into assay media to ≤1% v/v organic to maintain solubility and avoid precipitation.
For fluorescence studies, choose solvents with low background and well‑characterized polarity (e.g., cyclohexane, toluene, acetonitrile, ethanol) to probe ESIPT dual emission.
For O‑alkylation/acylation, dry polar aprotics (DMF/MeCN/THF) with mild base (K2CO3) are typical; stronger bases (NaH) in THF/DMF increase reactivity but risk side reactions.
Acetonitrile: good for HPLC and photophysics; moderate solubility; low UV background.
Storage and Reconstitution
Item-specific storage/shipping
Storage: Room temperature (as provided). Protect from light and moisture; keep container tightly closed to maintain integrity.
Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
Reconstitution/solution preparation
Item-specific instructions: Not specified for this item; refer to CoA/Spec Sheet.
General guidance (not a specification): Dissolve to prepare a concentrated stock in anhydrous DMSO or ethanol (e.g., 10–50 mM), vortex/sonicate as needed, then dilute into the working medium. Filter (0.2 µm PTFE) if particulate is observed. Avoid prolonged exposure to strong base once in solution to limit degradation or photophysical drift.
Stability considerations (general)
Store solid in the dark at ambient laboratory conditions; minimize repeated heating/cooling cycles. For solutions, aliquot and store at 2–8 °C or −20 °C depending on solvent to reduce oxidative discoloration; equilibrate to room temperature before use.
Always rely on the batch-specific CoA and SDS for definitive handling and storage instructions.
Structure and Identity
Brief description: 6-Methylflavonol is a flavonol (3‑hydroxyflavone) derivative bearing a methyl substituent at the 6‑position on the A‑ring, retaining the characteristic 3‑hydroxy‑4‑oxo chromenone core conjugated to a phenyl ring at C‑2.
Item-specific (from Product Data)
CAS: 6971-18-2
PubChem CID: 227445
InChIKey: 183025 (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.
Literature/computed identifiers and features (for reference only; not item specifications)
Structural class: flavonol (3-hydroxyflavone scaffold) with a 6‑methyl substituent.
Typical formula for 6‑methylflavonol (literature): C16H12O3; calculated formula weight ≈ 252.26 g/mol (literature).
Functional groups: phenolic OH at C‑3 (acidic, H‑bond donor/acceptor), conjugated 4‑oxo (lactone-like) within a 4H‑chromen‑4‑one, and an appended phenyl at C‑2; one methyl substituent at C‑6 increasing hydrophobicity.
2D structural description (general)
The backbone is a benzopyran-4‑one (chromenone) fused ring (A/C rings), with the B‑ring (phenyl) attached at C‑2. The 3‑OH and 4‑keto form an intramolecular H‑bond and enable ESIPT (excited-state intramolecular proton transfer) typical of 3‑hydroxyflavones. The 6‑methyl resides ortho to the 5‑OH position (which is absent in flavonols; here the phenol is at C‑3), subtly modulating electronics and sterics on the A‑ring.
Synthetic Utility
6‑Methylflavonol combines a phenolic OH with an adjacent conjugated ketone within a rigid, electron‑rich, polycyclic scaffold, providing multiple synthetic handles.
Key reactive sites (general)
3‑Phenolic OH: susceptible to O‑alkylation (Williamson ether) and O‑acylation (Steglich, acid chloride/pyridine) to modulate polarity and photophysics or to serve as protecting groups.
4‑Oxo/3‑OH chelate: enables metal complexation and serves as a directing motif in some transformations; tautomerism can influence reactivity under basic or photochemical conditions.
Aromatic rings: electrophilic substitution on the B‑ring is accessible; the 6‑methyl on the A‑ring is ortho/para‑directing and sterically biases substitution patterns.
Transformations and strategies
Halogenation followed by cross‑coupling (Suzuki–Miyaura, Buchwald–Hartwig after halogen installation, Sonogashira) to extend conjugation for custom fluorophores.
O‑Protect/O‑modify to probe structure–property relationships: convert 3‑OH to methyl/benzyl/aryl ethers or esters; subsequent deprotection restores the parent flavonol.
Nucleophilic addition to the carbonyl is typically disfavored by conjugation; however, reduction (e.g., NaBH4 with caution) can lead to dihydro derivatives altering ESIPT behavior.
Late‑stage C–H functionalization (e.g., directed ortho‑metalation on suitably protected derivatives) may be feasible to access position‑selective analogues.
Retrosynthetic note
Access via Algar–Flynn–Oyamada or Baker–Venkataraman‑type sequences is common for flavonols; a methylated acetophenone precursor can be used to install the 6‑methyl substituent prior to ring closure (literature strategies).
Target Specificity
This product is a small-molecule flavonol, not a biological affinity reagent.
Antigen/epitope, clone, isotype, species reactivity: Not applicable to this product type.
Item-specific targeting data: Not specified for this item; no target specificity information is provided in the Product Data.
For binding/interaction studies (e.g., with proteins, membranes, or metals), consult the primary literature on 3‑hydroxyflavone/6‑methylflavonol photophysics and binding assays; any such interactions are context‑dependent and not product specifications.
Häufig gestellte Fragen
How should this product be stored?
Store at room temperature.
What are the CAS number, molecular formula and molecular weight?
The CAS Number is 6971-18-2, the molecular formula is C16H12O3, and the molecular weight is 252.260 g/mol. InChIKey KLGALCMPMFKGDQ-UHFFFAOYSA-N.
What documentation is provided?
Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.
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