This compound belongs to the class of organic compounds known as 2'-hydroxychalcones. These are organic compounds containing chalcone skeleton that carries a hydroxyl group at the 2'-position.
External Descriptors
Chalcones and dihydrochalcones
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
330.300 g/mol
XLogP3
3.400
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
6
Rotatable Bond Count
6
Exact Mass
330.11 Da
Monoisotopic Mass
330.11 Da
Topological Polar Surface Area
85.200 Ų
Heavy Atom Count
24
Formal Charge
0
Complexity
429.000
Isotope Atom Count
0
Defined Atom Stereocenter Count
0
Undefined Atom Stereocenter Count
0
Defined Bond Stereocenter Count
1
Undefined Bond Stereocenter Count
0
The total count of all stereochemical bonds
1
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 vendor-validated biological or analytical test protocols are provided for this item.
General starting points (user-optimized):
Preparation of analytical standard: Accurately weigh 5–10 mg, dissolve in dry DMSO or MeOH to 1.0–10.0 mg/mL, sonicate if necessary, filter (PTFE, 0.22 µm) before LC-UV/LC–MS.
Stock solution for assays: Prepare 10–50 mM in DMSO; store aliquots at −20 °C protected from light; thaw once and dilute into assay buffer keeping final DMSO ≤1–2%.
TLC/HPLC monitoring: UV detection at 254 nm and an additional longer-wavelength channel (e.g., 330–360 nm) improves sensitivity for conjugated chalcones.
For any application requiring validated performance (e.g., QC reference), consult the lot-specific CoA for purity/identity and qualify the method in your lab.
Biological Roles
General biochemistry context (no medical/clinical claims):
Chalcones are open-chain precursors in the biosynthesis of flavonoids in plants. Enzyme chalcone synthase forms chalcone scaffolds from p-coumaroyl-CoA and malonyl-CoA, and chalcone isomerase converts them to flavanones in vivo (literature).
Phenolic and methoxy substitution patterns modulate redox behavior, metal chelation, and UV absorption. Such compounds often function in plants as pigments, UV screens, or signaling molecules; they can also influence plant–microbe interactions (literature, general).
In biochemical assays, chalcones are frequently used as tool compounds for studying Michael acceptor reactivity with nucleophilic residues in proteins (e.g., cysteine) and for probing structure–activity relationships across the flavonoid/chalcone space.
Item-specific biological data (targets, pathways, activities) are not provided for this product; users should consult primary literature for mechanistic insights relevant to their assays and validate activity under their exact experimental conditions.
Buffer Applications
This compound is a hydrophobic small molecule and is not a buffer component. It does not constitute a buffering system or maintain pH.
Practical guidance:
For biochemical assays, dissolve in DMSO or ethanol to make a concentrated stock, then dilute into the working buffer (e.g., phosphate, HEPES) keeping co-solvent ≤1–2% v/v to avoid precipitation.
For tests requiring phenolate forms, adjust buffer pH above the phenolic pKa (typically ~9–10 for phenols, literature generalization), but note that high pH can induce chalcone E/Z isomerization and possible oxidative degradation—control with inert atmosphere and minimal light.
Always pre-screen solubility at the intended buffer composition and temperature.
Green Alternatives
Consider solvent and reagent choices that lower environmental impact while maintaining performance with chalcone chemistry.
Greener solvent swaps (literature guidance):
Reaction medium for base-catalyzed cyclizations or conjugate additions:
Instead of DMF/DMSO: Use bio-derived 2-methyltetrahydrofuran (2-MeTHF) or Cyrene (dihydrolevoglucosenone) where compatible; both dissolve many chalcones and support organocatalysis. Evaluate basicity compatibility (Cyrene may react under strong base).
Workup/extraction:
Replace chlorinated solvents (DCM) with ethyl acetate or MTBE; both provide good partitioning for phenolic chalcones and lower persistence.
Crystallizations:
Favor ethanol or isopropanol over methanol/acetone where solubility permits.
Comparison snapshot (illustrative):
DCM vs EtOAc: Similar extraction efficiency for many chalcones; EtOAc has better EHS profile and is biodegradable.
THF vs 2-MeTHF: 2-MeTHF offers lower peroxide tendency, higher boiling point, and bio-based origin; performance in conjugate additions often comparable.
Reagent considerations:
Demethylation of methoxy groups: Opt for milder reagents (e.g., AlCl3/thiols, ionic liquids) or catalytic systems instead of stoichiometric BBr3/TMSI when feasible.
Hydrogenations: Employ transfer hydrogenation (e.g., formic acid/triethylamine, HCO2NH4) or heterogeneous catalysts recoverable by filtration.
Note: Validate solvent/reagent changes by small-scale screening; monitor isomerization and phenol oxidation, which can be sensitive to solvent polarity and dissolved oxygen.
Pharmaceutical Uses
No pharmacopeial grade or excipient designation is provided for this item.
Contextual, non-clinical information:
Chalcone derivatives are commonly used as research standards and reference materials in analytical method development (e.g., LC-UV/LC–MS) for profiling polyphenolic constituents in botanicals and complex matrices.
In preformulation research, compounds of this class are often evaluated for solubility enhancement techniques (co-solvents, cyclodextrin inclusion, amorphous dispersions) and solid-state characterization (polymorph screening), but such use is strictly for R&D.
If incorporation into dosage-form research is contemplated, ensure source material quality (impurities, residual solvents) and stability data are established. For this specific item, Grade/Purity is not specified; refer to CoA/Spec Sheet.
No therapeutic claims are made or implied. For regulatory work, verify identity, purity, and stability with your QA unit and consult all relevant guidelines.
Physical Properties
Item-specific properties (Product Data):
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Storage Conditions: Room temperature (as provided).
Typical/literature properties for substituted chalcones (reference values; verify experimentally):
Physical state: usually a yellow to orange crystalline solid for conjugated chalcones with multiple phenolic/methoxy groups (literature, qualitative).
UV-Vis: strong π→π* absorption in near-UV; phenolic/methoxy substitution often gives bands around 330–380 nm with additional bands at ~240–280 nm (literature ranges; exact λmax depends on solvent and substituents).
Solubility profile (qualitative, literature):
Good solubility in polar aprotic organics (DMSO, DMF) and polar protic solvents (MeOH, EtOH, acetone); poor solubility in water due to hydrophobic aryl core and ether groups; increased in basic aqueous media via phenolate formation.
Acid–base behavior: two phenolic OH groups (typical phenol pKa ~9–10; methoxy substitution can modestly modulate acidity; literature, qualitative).
Partitioning: expected moderate-to-high lipophilicity due to tri-methoxy and aryl groups; exact logP not established here.
Melting point, boiling point, density, refractive index: Not specified for this item; refer to CoA/Spec Sheet.
Notes for users:
Spectral characterization: 1H NMR typically shows vinylic doublets (J ~15–16 Hz for E-chalcone), phenolic OH (often downfield/broad), and anisole OCH3 singlets; IR shows strong C=O (~1650–1670 cm−1) and C=C conjugation bands (literature, qualitative).
Quality and Grades
Item-specific quality 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.
Context and guidance:
For small-molecule research reagents like chalcones, “research grade” typically targets high chemical purity for synthetic and analytical work, but may not meet pharmacopeial monographs. When purity is provided on the CoA, it is commonly determined by HPLC/UPLC with UV detection and corroborated by NMR and MS.
If low-UV or LC/MS applications are intended, inquire about residual solvents, inorganic content (ash), and UV background absorbance. For photophysical or biological assays, lot-specific purity and isomer ratio (E/Z chalcone) can be critical.
Phenolic compounds can slowly oxidize or discolor upon prolonged light/air exposure; suppliers may package under inert atmosphere or with desiccant. If the listing specifies such measures on the label/CoA, retain them to preserve quality.
Verification: For quantitative work, perform an incoming quality check (1H NMR integration, HPLC purity, water content by KF if applicable). Absent a stated water limit or peroxide specification on this item, treat as “Not specified for this item; refer to CoA/Spec Sheet.”
Reaction and Applications
This molecule is a multifunctional building block within the chalcone (α,β-unsaturated aryl ketone) family and supports diverse transformations.
Michael acceptor chemistry: The conjugated enone undergoes 1,4-conjugate additions from soft nucleophiles (thiols, malonates, enamines, cuprates). Phenolic substituents can direct reactivity and affect rate via resonance.
Hydrogenation/reduction: Selective 1,4-reduction of the C=C (e.g., Pd/C, H2) affords saturated dihydrochalcones; 1,2-reduction of the carbonyl (NaBH4, selectrides) yields allylic alcohols. Chemoselectivity is tunable by catalysts/solvent.
Cyclization to flavanones/flavones: Base- or acid-catalyzed intramolecular cyclization (chalcone isomerization) gives flavanones; oxidative/Dehydrogenative protocols yield flavones. Lewis acids (AlCl3, BF3·Et2O) or NaOH/EtOH conditions are commonly used (literature).
Cross-coupling handles: While this structure lacks halogens, O‑methyl groups can be demethylated (e.g., BBr3) to access polyphenols for further derivatization (acylation, alkylation, etherification) or late-stage metalation strategies.
Photochemistry/E–Z control: UV irradiation/base can induce E↔Z isomerization around the C=C, useful for studying conjugation effects or generating isomer libraries; monitor by 1H NMR (Jtrans ~15–16 Hz).
Analytical reference: Employed as a standard for method development in polyphenol/chalcone LC-UV profiling due to pronounced UV bands and ionizable phenols.
Practical tips:
Exclude strong oxidants; phenols may oxidize or polymerize under harsh conditions. Use inert atmosphere and light protection when extended heating is required.
Drying: If trace water matters (e.g., base-catalyzed cyclizations), dry by co-evaporation with toluene or store over P2O5 in a desiccator (do not contact solid directly).
Reaction Conditions
General literature guidance for typical transformations on chalcones; optimize for this substrate’s substitution pattern:
Solvents: MeOH, EtOH, acetonitrile, 2-MeTHF, or toluene (for organometallics).
Temperature/time: 0–25 °C for soft nucleophiles (0.5–6 h); −78 to 0 °C for cuprates; yields often 60–90% (literature ranges).
Reductions:
1,2-selective: NaBH4 in MeOH/EtOH at 0–25 °C, 0.5–2 h; quench cautiously.
1,4-selective: H2 (1–3 bar) over Pd/C or Pt/C in EtOH/EtOAc at 25–50 °C, 2–6 h.
Cyclization to flavanones:
Conditions: NaOH (10–30 mol%) in EtOH/H2O or K2CO3 in MeOH at 25–60 °C; 1–8 h. Alternative Lewis acids: AlCl3, BF3·Et2O in DCM/EtOAc.
Demethylation (to unveil additional phenols):
BBr3 (1–3 eq per methoxy) in DCM at −78→0 °C, 2–6 h; aqueous workup. Milder options include AlCl3/EtSH or ionic liquids; monitor to avoid over-deprotection.
Photochemical E/Z isomerization:
UV-A/UV-B irradiation in acetonitrile or ethanol; minutes to hours with steady-state lamps; monitor by HPLC.
Notes:
Oxygen exclusion (N2/Ar) and amber glassware help suppress oxidation.
Phenolate formation at high pH alters solubility/reactivity; titrate base and verify by TLC/HPLC.
All conditions above are literature-level guidance; run small pilot reactions and confirm with analytical data for this specific substrate.
Safety and Handling
Authoritative safety information must be taken from the product SDS.
Product Data safety fields provided: Signal word, H-statements, GHS class, pictograms: Not specified for this item; refer to SDS.
General handling guidance for polyphenolic chalcones (literature/practice-based):
GHS expectation: Many chalcones are unclassified or may present eye/skin irritation hazards; treat as harmful if swallowed/inhaled/absorbed until SDS confirms otherwise.
PPE: Use lab coat, safety glasses or goggles, and appropriate chemically resistant gloves (e.g., nitrile). Handle in a fume hood to avoid dust/aerosol inhalation.
Avoid: Contact with strong oxidizers (phenolic/aromatic substrates can undergo oxidative coupling), strong bases/acids that may cause isomerization or hydrolysis of protecting groups.
Dust control: Minimize dust generation; use weigh boats and antistatic tools. Wipe spills with damp disposable towels; avoid dry sweeping.
First aid (overview; consult SDS): move to fresh air for inhalation; wash with soap/water for skin contact; rinse eyes with water for several minutes and seek advice; if ingested, rinse mouth, do not induce vomiting, obtain medical attention.
Thermal/photochemical sensitivity: Extended conjugation can lead to photochemistry (E/Z isomerization) under strong UV. Store protected from strong light as good practice.
Waste: Collect solid and solvent rinses as organic hazardous waste per institutional and local regulations.
Solvent Selection
Solubility and handling strategy for chalcone scaffolds with phenolic/methoxy substitution:
Polarity class: Moderately lipophilic aromatic with polar functions (conjugated ketone, phenols, aryl ethers). Suitable for polar organic solvents.
Poorly soluble: water and very nonpolar alkanes (hexanes) at room temperature.
Stock solutions for assays: Prepare concentrated stocks in dry DMSO (e.g., 10–50 mM) and dilute into aqueous buffers with co-solvent ≤1–2% v/v DMSO to minimize precipitation; adjust pH if phenolate formation is acceptable.
Extraction/partitioning: Liquid–liquid extraction from reaction media typically favors EtOAc or MTBE against aqueous phases; basic wash (carbonate/bicarbonate) can deprotonate phenols (increase aqueous transfer) if desired, then re-acidify to recover.
Crystallization: Ethanol, methanol, or EtOAc/hexane mixtures often give good crystallization behavior for chalcones; screen solvent pairs to manage oiling out.
When to choose alternatives: For water-sensitive downstream steps, use anhydrous acetonitrile or THF; for greener profiles, consider 2-MeTHF or EtOAc instead of chlorinated solvents (see Green Alternatives).
Storage and Reconstitution
Item-specific storage:
Storage Conditions: Room temperature (as provided in Product Data). As good practice for conjugated phenolics, store tightly closed, in a dry, cool place, protected from light and ambient moisture.
Shipped In: Not specified for this item; refer to CoA/Spec Sheet.
Reconstitution and solution handling (general guidance):
Solvents: DMSO, DMF, MeOH, or EtOH typically dissolve chalcones readily. For aqueous use, prepare a DMSO stock and dilute into buffer with vigorous mixing.
Concentrated stocks: 10–50 mM in dry DMSO are common for screening; filter sterilize if sterility is required (0.22 µm PTFE). Avoid repeated freeze–thaw of solutions; aliquot upon first dissolution.
Light/air sensitivity: Minimize exposure to strong light; use amber vials. Purge headspace with inert gas for long-term storage of solids or solutions.
Stability: Specific long-term stability data are not provided for this item; refer to CoA/Spec Sheet. As a general rule, phenolic chalcones are stable for months as solids under dry, dark conditions; solutions are best prepared fresh or stored ≤1–4 weeks at −20 °C (verify by HPLC).
Research Use Note: For research use only.
Structure and Identity
Concise description: 4,2'-Dihydroxy-3',4',6'-trimethoxychalcone is a polyphenolic chalcone bearing one phenyl ring with a para-hydroxyl and the second phenyl ring bearing one ortho-hydroxyl and three methoxy substituents. The scaffold is an α,β-unsaturated aryl ketone (chalcone) linking the two rings via a propenone bridge (Ar–CO–CH=CH–Ar').
Item-specific identifiers (Product Data):
CAS: 69616-74-6
SKU: D956688
InChIKey: Not specified for this item; refer to CoA/Spec Sheet. (Product Data listed value appears incomplete.)
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/structural description):
Conjugation: extended π-system across two aryl rings and the enone, typically strong UV absorption in the near-UV (literature, qualitative).
Regiochemistry: Ring A (chalcone “benzoyl” ring) carries a 4‑OH; Ring B (the “cinnamyl” ring) carries 2′‑OH and 3′,4′,6′‑OCH3.
Stereochemistry: the enone typically exists as the E (trans) isomer around the C=C bond in chalcones (literature prevalence), though isomerization can occur under UV/base.
Computed/literature identifiers (for reference only; verify against CoA):
PubChem CID: 5375973 (literature index)
Common class: substituted chalcone (flavonoid precursor class).
Synthetic Utility
Strategic roles of 4,2'-dihydroxy-3',4',6'-trimethoxychalcone in synthesis (general literature guidance):
Polyphenol precursor: Demethylation (e.g., BBr3, AlCl3/thiol systems) unveils catechol/pyrogallol-like motifs, enabling metal chelation, oxidative coupling, or further protection–deprotection sequences.
Michael acceptor platform: The enone allows modular installation of nucleophiles (S, C, N) at the β-position, furnishing diversified dihydrochalcones or β-substituted ketones under soft nucleophile conditions.
Cyclization manifold: Base- or acid-promoted intramolecular additions deliver flavanones; oxidative methods extend to flavones/aurones—useful entries into flavonoid libraries.
Late-stage functionalization: Phenolic OH can be selectively protected (silyl, benzyl, carbonate) or derivatized (acylation, sulfonylation) to fine-tune electronics for subsequent steps. Methoxy groups can direct ortho-metalation after appropriate activation.
Photochemical/E/Z control: Access to both E- and Z-chalcones provides handles for stereoelectronic studies; Z isomers can exhibit distinct reactivity in cycloadditions and hydrogenations.
Operational notes:
Manage competing 1,2- vs 1,4-reduction by solvent/catalyst choice (e.g., NaBH4/i-PrOH favors 1,2-addition; Pd/C–H2 favors 1,4-). Monitor by NMR (allylic OH vs saturated ketone signatures).
Protect phenols when employing strong bases or electrophilic catalysts to avoid polymerization or overreaction; staged deprotection restores the target polyphenol pattern.
Target Specificity
Not applicable. This product is a small-molecule chalcone, not an antibody, enzyme, or affinity reagent. No antigen/epitope or isotype information applies.
If using as a biochemical probe, define “target specificity” empirically for your system via orthogonal assays (e.g., covalent labeling patterns, competition experiments). No target claims are made for this item.
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.
