This compound belongs to the class of organic compounds known as 8-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C8 atom of the flavonoid backbone.
External Descriptors
Flavones and Flavonols
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
378.800 g/mol
XLogP3
3.800
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
7
Rotatable Bond Count
4
Exact Mass
378.051 Da
Monoisotopic Mass
378.051 Da
Topological Polar Surface Area
94.500 Ų
Heavy Atom Count
26
Formal Charge
0
Complexity
566.000
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
Molarity Calculator
Determine the necessary mass, volume, or concentration for preparing a solution.
Dilution Calculator
Determine the dilution needed to prepare a stock solution.
Reconstitution Calculator
Recensioni
Recensioni dei clienti
Application Protocols
No manufacturer-tested application protocols are provided for this SKU. General starting points for research use include:
Stock preparation: Dissolve in DMSO to 10–50 mM; vortex and sonicate briefly if needed; filter (0.2 µm PTFE) for analytical use.
Antioxidant assays (e.g., DPPH/ABTS, literature methods): Prepare serial dilutions in MeOH or buffer with ≤1% DMSO; measure absorbance changes at method-specific wavelengths; include Trolox or quercetin as comparators.
LC–MS/LC–UV method development: Start with C18 column, water/MeOH or water/ACN gradients (0.1% formic acid); detect at 270–360 nm; adjust gradient based on retention and peak shape.
These are general suggestions; adapt to your system and consult peer-reviewed procedures. For validated, item-specific protocols, refer to the CoA/Spec Sheet when available.
Biological Roles
Literature/general perspective (no therapeutic claims):
Origin: Chlorflavonin is reported as a halogenated flavonoid natural product isolated from certain lichen/fungal sources. As with many flavonoids, it features a conjugated chromone scaffold and phenolic groups.
Biochemical activities: Polyphenolic flavonoids often exhibit redox activity (radical scavenging), metal chelation, and the ability to modulate enzyme function through hydrogen bonding and π–π interactions. Halogenation can influence membrane affinity, metabolic stability, and target binding.
Assay use: Serves as a reference analyte in antioxidant capacity assays (e.g., DPPH/ABTS), enzyme inhibition panels (e.g., kinases/oxidoreductases in exploratory screens), and as a spectral standard due to defined UV–Vis bands of the flavone core.
ADME considerations (in vitro, general for flavonoids): Limited aqueous solubility, potential for glucuronidation/sulfation by phase II enzymes, and protein binding via hydrophobic and H-bonding interactions. Halogen substitution may reduce metabolic turnover relative to non-halogenated analogs.
Important: All uses are for research purposes only (per product data). For any biological testing, ensure vehicles (e.g., DMSO ≤1%) and pH are controlled to avoid artifactual outcomes arising from polyphenol autooxidation or aggregation.
Buffer Applications
Chlorflavonin is not a buffering reagent and does not serve as a primary component of common biological buffer systems. For experiments requiring buffered conditions (e.g., bioassays with chlorflavonin dissolved in DMSO), select an appropriate buffer (PBS, HEPES, Tris, etc.) and verify compound stability across the working pH. Consider:
Maintain DMSO cosolvent typically ≤0.5–1% v/v to minimize solvent effects.
Avoid strongly basic buffers for prolonged incubations to limit phenolate-driven degradation/oxidation.
No item-specific buffer recipes apply to this compound.
Green Alternatives
Although chlorflavonin is a solid analyte/building block rather than a process solvent, greener choices can be made for its handling and transformations.
Greener solvent choices for dissolution/workup (general guidance):
Replace DMF/DMAC with ethanol or acetone where feasible (e.g., recrystallization, extractions). For analytics, ethanol/water gradients can substitute for ACN/MeOH in some UV methods.
Use 2‑MeTHF or CPME instead of toluene/THF for certain extractions or couplings when solubility permits.
Comparison (general pros/cons):
Ethanol: renewable, low toxicity; slightly lower solvating power vs MeOH/DMF; higher boiling point improves recrystallization control.
Acetone/EtOAc: readily biodegradable; good for partitioning and workups; may have limited solubility for highly polar polyphenols.
2‑MeTHF: bio-based, hydrophobic; useful in metal-catalyzed couplings; water content must be controlled for base-sensitive steps.
Process-intensity and waste minimization:
Favor catalytic cross-couplings with ligand systems enabling aryl chloride activation at lower temperatures (reduced energy input).
Employ aqueous micellar catalysis or ethanol/water media for certain O‑alkylations and acylations to reduce reliance on dipolar aprotics, where compatible.
Choose solid-supported scavengers for metal removal to minimize solvent volumes in workup.
Note: Verify solubility and stability of chlorflavonin in the chosen green solvent system before scale-up.
Pharmaceutical Uses
No excipient or pharmacopeial status is specified for this item. Chlorflavonin is supplied for research use only (per product data) and is not indicated for clinical or diagnostic applications.
Research/formulation context (general):
Can serve as a reference standard for analytical method development (LC–UV/LC–MS) targeting halogenated flavonoids in natural-product characterization or metabolism studies.
For in vitro studies, stock solutions are commonly prepared in DMSO; for in vivo formulation development research (non-clinical), solubilizing systems such as PEG400/ethanol/saline or cyclodextrin complexes are sometimes evaluated to improve exposure—subject to institutional policies and safety review.
Always verify regulatory constraints and quality requirements before any use beyond basic laboratory research.
Physical Properties
Item-specific specifications (for this SKU):
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
Other specifications (mp, bp, density, refractive index, UV cutoff, water content, metal limits, etc.): Not specified for this item; refer to CoA/Spec Sheet.
Literature/general properties for chlorinated flavonoids like chlorflavonin (non-spec, for context only):
Physical state: typically a yellow to yellow-brown crystalline solid due to extended conjugation in the chromone system.
Solubility: sparingly soluble in water; soluble in polar organic solvents such as DMSO, DMF, methanol, ethanol, and acetone; limited solubility in nonpolar hydrocarbons. Aqueous solubility may improve at higher pH due to phenolate formation.
UV–Vis: strong absorption in the near-UV (~250–380 nm) with band I/II transitions characteristic of flavones (literature), practical for HPLC-UV detection.
Acid–base behavior: phenolic pKa values for related flavonoids are typically in the range ~7–10 (literature), enabling pH-dependent ionization and metal chelation.
Practical notes:
For analytical work, prepare stock solutions in dry DMSO or MeOH; filter through 0.2 µm to remove particulates.
Protect from strong light to minimize photooxidation and color changes in solution (general for polyphenolics).
Quality and Grades
Grade/Purity for this SKU: Not specified for this item; refer to CoA/Spec Sheet.
Context and expectations:
Without a declared grade (e.g., analytical reference standard grade, ≥98% purity, HPLC grade), end-users should consult the lot-specific Certificate of Analysis (CoA) for:
Assay purity (e.g., HPLC/UPLC area %), identity confirmation (NMR, MS, HRMS), and water/ash content if available.
Residual solvents, chromatographic profile, and UV absorbance characteristics if intended for analytical method development.
Stabilizers: Not specified for this item; refer to CoA/Spec Sheet. Flavonoid solids typically do not require stabilizers; however, antioxidants or inert-atmosphere packaging can be useful to limit oxidation.
Implication for use:
For quantitative bioassays or as a reference material, verify potency/purity by independent HPLC or qNMR.
If trace-metal sensitivity is critical (e.g., for complexation studies), check metal content or pre-treat with chelating resins and re-crystallization as needed.
Reaction and Applications
Research applications (literature/general for chlorinated flavonoids):
Chemical biology probe/reference: Used as a characterized polyphenolic standard to study structure–activity relationships (SAR) of halogenated flavones/flavonols, redox properties, and UV–Vis signatures.
Metal chelation studies: Phenolic and carbonyl functionalities support bidentate chelation (e.g., 3-hydroxy-4-keto or catechol-like motifs); complexation alters spectral and redox behavior.
Antioxidant/oxidation chemistry: Serves as a substrate in radical-scavenging assays (DPPH, ABTS) and electrochemical studies to benchmark electron-donating capacity (literature context; not an item spec).
Transformations and derivatization (synthetic applications):
O‑alkylation/O‑acylation: Phenolic OH groups can be selectively protected or derivatized (e.g., methyl/benzyl ethers; acetates/carbonates) to modulate solubility and reactivity.
Cross-coupling on aryl chloride: With appropriate activation and catalysts (e.g., Pd(0)/ligand systems), the chloro substituent can undergo Suzuki–Miyaura, Buchwald–Hartwig (C–N), or Sonogashira couplings to generate analog libraries.
Electrophilic substitution/halogen–metal exchange is generally less selective due to multiple activated positions; protecting-group strategies recommended.
Practical tips:
Drying: For base-promoted O‑alkylation, rigorously dry solvents (DMF/acetone) and use anhydrous inorganic bases (K2CO3, Cs2CO3) to favor clean ether formation.
Degassing: For Pd-catalyzed couplings, sparge with N2/Ar and employ degassed solvents to maintain catalyst activity.
Analytics: Track reactions by LC–MS and UV (band I/II transitions); phenolic tautomers may give multiple spots in TLC under different pH conditions.
Reaction Conditions
General literature-guided conditions for common transformations of chlorinated flavonoids (reference guidance; optimize per substrate):
O‑Alkylation (ether formation):
Solvent: dry DMF, acetone, or acetonitrile.
Base: K2CO3 or Cs2CO3 (1.5–3.0 eq), 0.1–0.5 M.
Electrophile: alkyl halide or sulfate (1.2–2.0 eq).
Temperature/time: 40–80 °C, 2–16 h.
Notes: Protect more acidic phenols first if selectivity is required; monitor by LC–MS.
O‑Acylation/Carbamate formation:
Reagents: Acyl chlorides or anhydrides; DIPEA/Et3N as base; DMAP (cat.).
Solvent: DCM, THF, or EtOAc.
Temperature: 0 °C to rt, 1–4 h.
Notes: Avoid excess base to limit chromone opening.
Suzuki–Miyaura coupling at aryl chloride:
Catalyst: Pd2(dba)3 or Pd(OAc)2 (1–3 mol%) with bulky electron-rich ligands (e.g., SPhos/XPhos).
Base: K3PO4, Cs2CO3, or K2CO3 (2–3 eq).
Solvent: 1,4‑dioxane/H2O, toluene/H2O, or EtOH/H2O.
Temperature/time: 80–110 °C, 4–24 h.
Notes: Protect phenols as needed to prevent catalyst deactivation; degas thoroughly.
Hydrogenolysis of benzyl ethers (for deprotection):
Catalyst: Pd/C (5–10 wt%).
Solvent: EtOH or EtOAc; 1–3 bar H2.
Temperature: rt to 40 °C, 2–8 h.
Yields and exact conditions vary with substitution pattern; run small-scale screens to identify optimal ligands/bases and protection strategies.
Safety and Handling
Item-specific hazard information (GHS/SDS):
Signal word: Not specified for this item; refer to SDS.
Hazard statements (H-phrases): Not specified for this item; refer to SDS.
Pictograms: Not specified for this item; refer to SDS.
GHS classification: Not specified for this item; refer to SDS.
General laboratory safety guidance for flavonoid polyphenols (not a substitute for the SDS):
Likely hazards: may cause skin/eye irritation and respiratory irritation if dust is generated. Avoid inhalation and contact.
PPE: lab coat, safety glasses or goggles, and suitable gloves (e.g., nitrile). Handle powders in a fume hood to control dust.
Incompatibilities: strong oxidizing agents (phenolic oxidation), strong bases or strong acids may lead to degradation or hydrolysis of sensitive motifs; avoid prolonged exposure to alkali and light in solution.
First aid (general):
Eye contact: rinse cautiously with water for several minutes; remove contact lenses if present and easy; seek medical attention if irritation persists.
Skin contact: wash with soap and water; remove contaminated clothing; seek medical attention if irritation develops.
Inhalation: move to fresh air; seek medical attention if symptoms occur.
Ingestion: rinse mouth; do not induce vomiting; seek medical advice.
Handling/storage: keep container tightly closed, dry, and protected from light at room temperature (per product data). Avoid generating dust and static.
Always consult the product SDS for authoritative and item-specific safety information before use.
Solvent Selection
Polarity and dissolution behavior (literature/general for flavonoids):
Preferred solvents for stock solutions: DMSO and DMF (excellent solvating power for polyphenols and aryl chlorides). Methanol and ethanol are often adequate for preparative work and analytics.
Aqueous media: Very low intrinsic solubility; solubility can be increased by cosolvents (≤1–2% DMSO in assay buffers), cyclodextrins, or by adjusting pH to form phenolates (note potential chemical changes and assay interference).
When to choose specific solvents:
Analytical HPLC: MeOH/H2O or ACN/H2O with formic acid or ammonium formate modifiers for LC–UV/LC–MS (avoid high pH to limit degradation).
Preparative work: Hot ethanol or methanol for recrystallization; DMSO for high-concentration stocks.
Spectroscopy: MeOH or EtOH for UV–Vis; DMSO‑d6 or acetone‑d6 for NMR.
Quick comparison (general):
DMSO vs DMF: DMSO offers better biocompatibility in small volumes for bioassays; DMF can be advantageous for certain coupling reactions but is less desirable in biological systems.
MeOH vs EtOH: MeOH gives stronger elution and better UV transparency at shorter wavelengths; EtOH is greener/safer for scale-up and workup.
Container: Keep tightly closed in the original container. Protect from light and moisture to minimize oxidative or photolytic degradation typical of polyphenols.
Stability: Item-specific shelf life and retest dates are provided on the CoA/label where applicable. Avoid prolonged exposure to air and elevated humidity.
Reconstitution/preparation of solutions (general guidance):
Solvents: Prepare concentrated stocks in anhydrous DMSO (commonly 10–50 mM) or methanol. For biological assays, dilute into buffer or media ensuring final DMSO ≤0.5–1%.
Filtration: For analytical work, pass solutions through a 0.2 µm PTFE filter to remove particulates.
Light/temperature: Prepare and store solutions in amber vials at 2–8 °C for short-term use (days). For longer-term storage, aliquot and freeze at −20 °C to −80 °C to reduce freeze–thaw cycles.
Freeze–thaw: Minimize cycles; thaw at room temperature, vortex to redissolve, and inspect for precipitation or color change before use.
Note: If the CoA specifies different storage or stability instructions for your lot, follow the CoA/SDS as the source of record.
Structure and Identity
Product name: Chlorflavonin (natural-product type flavonoid)
CAS: 23363-64-6 (product data)
InChIKey: Not specified for this item; refer to CoA/Spec Sheet. (product data listed a non-standard token; authoritative ID should be taken from CoA/SDS)
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 (literature/general description):
Chlorflavonin is a chlorinated flavonoid of the flavone/flavonol family, consisting of a fused chromen-4-one (1-benzopyran-4-one) core with a pendant phenyl ring.
Contains multiple phenolic hydroxyl groups (typical for flavonoids) capable of hydrogen bonding and metal chelation.
Contains one aryl chloride substituent on the B-ring (positioning varies by specific substitution pattern reported in the literature), useful as a handle for cross-coupling derivatization.
2D description: one six-membered benzene ring fused to a heterocyclic pyrone ring (chromone), forming a planar polyaromatic system; a second benzene ring (B-ring) is attached at the 2-position of the chromone. Hydroxy groups are generally located on the A- and/or B-rings; a chlorine atom is present on the B-ring.
Notes:
Where exact positions, formula, and MW are critical, please consult the item-specific CoA/Spec Sheet for definitive identifiers and analytical data.
Synthetic Utility
Functional handles and reactivity (general for chlorinated polyphenolic flavones/flavonols):
Phenolic OH groups: amenable to selective protection (Me, Bn, silyl), acylation, carbonate/urethane formation; can direct metalation or chelation.
Aryl chloride: potential site for Pd-catalyzed cross-couplings (Suzuki–Miyaura, Buchwald–Hartwig, Sonogashira) with proper ligand design to activate the C–Cl bond.
Conjugated chromone: participates in electrophilic substitution on activated rings; undergoes hydrogen-bond-driven tautomerism that can affect reactivity.
Applications in synthesis:
Late-stage diversification: install substituents on the B‑ring via C–C/C–N coupling to generate SAR libraries.
Prodrug strategies (research): mask phenols (e.g., carbonate/ester pro-moieties) to improve lipophilicity and solubility for tool-compound studies.
Metal complexes: formation of defined chelates (e.g., with Al3+, Fe3+, Cu2+) used to probe coordination chemistry and spectroscopic shifts.
Retrosynthetic perspective:
Chlorflavonin frameworks can be accessed via Algar–Flynn–Oyamada oxidation, Baker–Venkataraman rearrangement from acylated o‑hydroxyacetophenones, or via Claisen–Schmidt condensations followed by cyclization—useful for analog synthesis and isotopic labeling.
Target Specificity
Not applicable. This product is a small-molecule flavonoid, not an antibody, enzyme, or oligonucleotide reagent. No antigen/epitope or species reactivity applies. For biochemical targets studied with chlorflavonin in the literature, consult primary sources; item-specific target data are not provided for this SKU.
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.
