This compound belongs to the class of organic compounds known as retrochalcones. These are a form of normal chalcones that are structurally distinguished by the lack of oxygen functionalities at the C2'- and C6'-positions.
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.
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
344.400 g/mol
XLogP3
3.200
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
6
Rotatable Bond Count
7
Exact Mass
344.126 Da
Monoisotopic Mass
344.126 Da
Topological Polar Surface Area
74.200 Ų
Heavy Atom Count
25
Formal Charge
0
Complexity
445.000
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
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Recensioni
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Application Protocols
Item-specific (Product Data)
Manufacturer Applications: Not specified for this item; refer to CoA/Spec Sheet.
General laboratory protocols (guidance only; not item specification)
Preparation of stock solutions: Dissolve the solid in anhydrous DMSO to 10–50 mM. For sensitive optical work, use amber vials and degassed solvent to limit photo- and oxygen-induced changes.
Working solutions for bioassays: Dilute DMSO stock into prewarmed buffer or media to achieve desired concentrations with ≤0.5–1% final DMSO. Verify absence of precipitation by visual inspection or light scattering.
HPLC assay: Reverse-phase C18, gradient 40–90% acetonitrile in water (0.1% formic acid), detection at 350 nm (plus full PDA scan). Typical injection 5–20 µL of 0.1–1.0 mg/mL solution.
TLC monitoring: Silica gel plates, eluent e.g., hexanes/EtOAc 3:1 to 1:1, visualize at 254 nm and with anisaldehyde or vanillin stains.
Purification tips: If tailing occurs, add 0.1–1% Et3N to eluent or switch to reverse-phase. Dry fractions under reduced pressure at ≤40 °C.
Controls and documentation
Include vehicle controls (DMSO only) and, where relevant, scavengers (e.g., glutathione) to probe nonspecific Michael addition in biochemical assays. Document lot number and preparation conditions for reproducibility.
Biological Roles
This section provides general biochemical context; it does not describe medical effects and is not specific to this SKU.
General background (literature)
Chalcones are open-chain flavonoid precursors found in plants, formed via chalcone synthase in the polyketide pathway. Hydroxy- and methoxy-substituted chalcones are common intermediates en route to flavones, flavanones, and aurones.
The α,β-unsaturated carbonyl can act as a soft electrophile for cysteine thiols, a consideration in enzymology assays where nonspecific covalent interactions may occur. Methoxy substitution increases lipophilicity and can modulate membrane permeability in cell-based experiments.
Utility in research (general)
Conjugated chalcones serve as chromophores for studying solvent effects, intramolecular hydrogen bonding, and charge-transfer transitions.
As privileged scaffolds, substituted chalcones are frequently included in screening libraries to probe covalent and noncovalent interactions with proteins; care should be taken to distinguish target-directed activity from Pan-Assay Interference (PAINS)-like behavior.
Practical notes
For biochemical assays, prepare concentrated DMSO stocks and dilute into assay buffers to ≤1% v/v DMSO final. Include reducing agents (e.g., 1–5 mM DTT) judiciously depending on whether thiol reactivity is desired or should be suppressed.
All uses are for research only; this product is not intended for diagnostic or therapeutic applications.
Buffer Applications
Applicability
As a neutral, largely hydrophobic small molecule, this compound is not used as a buffering agent. It does not define buffer capacity or pH control.
Practical guidance for assay buffers (general)
When used in biochemical or cell-based assays, the compound is typically added from a DMSO stock to a preselected buffer (e.g., PBS, HEPES, or Tris) appropriate for the biological system.
Keep final DMSO content ≤0.5–1% v/v to minimize solvent effects. Solubilization aids (0.01–0.1% nonionic surfactants such as Tween-20) can be considered if precipitation is observed.
Filter or centrifuge assay solutions if any turbidity appears; avoid prolonged exposure to strong base in buffer, which may promote side reactions at the enone or phenolic site.
Not specified for this item; refer to CoA/Spec Sheet for any lot-specific formulation notes.
Green Alternatives
Solvent and process considerations (general guidance)
Many operations with chalcones use chlorinated solvents or high-boiling dipolar aprotics. Where feasible, choose greener options without compromising performance.
Greener substitutions (literature/general)
Replace CH2Cl2 with ethyl acetate or 2-MeTHF for extractions and chromatography when polarity allows.
Use 2-MeTHF or CPME instead of THF for moisture-tolerant reactions; both offer reduced peroxide formation rate and improved safety profiles.
Favor MeOH/EtOH or acetonitrile (low toxicity, recyclable) over DMF/DMSO for base-mediated condensations when solubility permits.
Employ aqueous micellar catalysis (e.g., TPGS-750-M) for certain conjugate additions to minimize organic solvent usage.
Comparison snapshot (general)
THF → 2-MeTHF: similar polarity; 2-MeTHF is bio-derived, less miscible with water (easier workups), but may alter reaction rates/selectivity.
CH2Cl2 → EtOAc: greener and biodegradable; slightly higher polarity; boiling point higher (77 °C) impacting concentration.
DMF → MeCN: MeCN is less problematic toxicologically and easier to remove; lower donor number may affect certain base-catalyzed steps.
Waste minimization
Use catalytic rather than stoichiometric Lewis acids (e.g., Sc(OTf)3, FeCl3) for cyclizations where possible.
Implement inline chromatography alternatives (crystallization, trituration) leveraging the compound’s often strong coloration to monitor purity visually.
Pharmaceutical Uses
Scope of this section
No pharmacopoeial monograph or excipient role is provided for this SKU. Content below is general and for research/formulation development contexts only; no clinical claims are made.
General formulation context (literature/general)
Substituted chalcones are investigated in preformulation as lipophilic small molecules. For in vitro work, they are typically dosed from DMSO stocks. Limited aqueous solubility often necessitates co-solvents (PEG 400, ethanol), cyclodextrin inclusion, or lipid-based systems for exploratory delivery studies.
The strongly absorbing conjugated system may be leveraged as an intrinsic reporter in analytical development (UV detection in HPLC at ~340–380 nm typical for related chalcones).
Analytical considerations
Reverse-phase HPLC with water–acetonitrile (0.1% formic acid) is commonly used for assay and impurity profiling. Photodiode-array detection facilitates peak purity assessment due to strong chromophores.
Regulatory status
No pharmacopeia or GMP grade is indicated. Use is restricted to research and laboratory development. For any regulated use, a formal quality agreement, expanded impurity profile, and stability program would be required.
Item-specific note
Grade/Purity, stabilizers, and excipient roles: Not specified for this item; refer to CoA/Spec Sheet.
Physical Properties
Item-specific (Product Data)
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/computed properties (reference values; not item specification)
Estimated molecular formula: C19H20O6; FW ≈ 344.36 g/mol (derived from substitution pattern on a chalcone core)
Physical state: typically a yellow to orange crystalline solid for conjugated chalcones (literature trend)
Solubility profile: expected low aqueous solubility; soluble in common organic solvents (DMSO, DMF, methanol, ethanol, acetone, ethyl acetate, CH2Cl2) (literature)
UV–Vis: strong π→π* absorbance in the near-UV to visible owing to the extended enone–aryl conjugation; often λmax ~340–380 nm for related hydroxy/methoxy-chalcones (literature, indicative)
logP: likely moderate to high due to four methoxy groups and polyaromatic core; typical chalcone logP ~2–4 (literature, indicative)
Melting point, boiling point, density, refractive index, pKa: Not located in primary literature for this exact substitution pattern; consult primary references or CoA if available.
General notes
Intramolecular hydrogen bonding (2-OH⋯O=C) can influence tautomeric preference and spectral signatures. Solid-state coloration and UV absorbance are often sensitive to solvent polarity (solvatochromism) in this class.
Quality and Grades
Item-specific (Product Data)
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
What grade implies (general guidance)
If provided as “research grade,” this typically indicates suitability for general laboratory synthesis, screening, and mechanistic studies, without certified impurity profiling beyond the CoA.
If offered as “>95%” or “>98%” purity on CoA, this commonly reflects HPLC/GC/NMR assay of the bulk lot. Low residual solvent levels and controlled inorganic content may be noted where relevant.
Absence or presence of stabilizers: For activated enones, stabilizers are uncommon but information would be listed explicitly in the CoA/specification if used. None are specified here.
Practical implications
For sensitive applications (e.g., quantitative SAR, photophysical measurements), verify purity by independent NMR/HPLC and check for geometric isomerism (E/Z at the α,β-double bond) if relevant.
If trace water or protic impurities could interfere (e.g., during strong-base-mediated transformations), consider drying the solid in vacuo at ambient temperature before use, consistent with its thermal stability.
Always defer to the lot-specific CoA for definitive data (assay method, residual solvents, impurity profile, water content). Where values are not specified here, they are Not specified for this item; refer to CoA/Spec Sheet.
Reaction and Applications
General reactivity profile (literature)
As an α,β-unsaturated aryl ketone, this chalcone is a competent Michael acceptor toward soft nucleophiles (thiols, malonates, enamines) under base or Lewis acid catalysis. The electron-rich tetramethoxy ring increases conjugation, potentially enhancing electrophilicity and enabling visible absorption.
The 2-hydroxy group can form a six-membered intramolecular H-bond with the carbonyl, stabilizing the trans-enone and influencing reactivity and NMR shifts.
1,4-Additions: Organocuprate additions in THF or toluene at −78 to 0 °C; Michael additions of malonates with base (DBU, K2CO3) in MeCN or DMF.
Cyclizations to flavones/aurones: Oxidative cyclization of 2′-hydroxychalcones to flavones with I2/DMSO, PhI(OAc)2, or DDQ; aurone formation under Au- or Ag-catalyzed conditions or with basic peroxide protocols.
Hydrogenation: Selective 1,4-hydrogenation of the enone (Pd/C, H2) or full saturation to the saturated ketone/alcohol under forcing conditions.
O-Alkylation/acylation: Phenolic OH can be protected (e.g., methylation with MeI/K2CO3) or diversified for probe synthesis.
Use contexts (general)
Building block for flavonoids and related polyphenolic scaffolds.
Chromophoric handle for photophysical studies of donor–acceptor systems due to multiple methoxy donors and enone acceptor.
Potential electrophilic fragment for chemical biology screening, provided assay conditions mitigate nonspecific thiol reactivity.
Note: No manufacturer application notes were provided for this SKU beyond Research use only.
Reaction Conditions
The following are literature-style general conditions for chalcone-class substrates and should be adapted after small-scale screening; they are not specifications for this SKU.
Michael additions (1,4-)
Typical: malonate (1.5–2.0 equiv), base (DBU 10–20 mol% or K2CO3 1–2 equiv), MeCN or DMF, 25–60 °C, 2–12 h; yields commonly 60–90% depending on nucleophile and substitution.
Thiol additions: catalytic base (Et3N 10 mol%) in MeOH or THF, rt–40 °C, 1–6 h; monitor by TLC/UV.
Oxidative cyclization to flavones (from 2′-hydroxychalcones)
I2 (1.2–2.0 equiv) in DMSO (neat or 5–10 mL/g), 80–120 °C, 2–8 h; workup with Na2S2O3; yields frequently 50–85%.
PhI(OAc)2 (1.5 equiv) in MeCN, rt–50 °C, 1–3 h; often milder with sensitive substituents.
Aurone formation
AuCl3 (5–10 mol%) in MeCN or nitromethane, rt–60 °C, 2–6 h, oxidative conditions as required.
Reductive transformations
1,4-hydrogenation: Pd/C (5–10 wt%), H2 (1–3 atm), EtOH/EtOAc, rt–40 °C, 2–8 h.
Luche reduction (1,2-selective): NaBH4 (1.2–2.0 equiv), CeCl3·7H2O (1.5 equiv), MeOH, 0–25 °C, 0.5–2 h.
Analytical and monitoring
Strong UV absorbance enables convenient TLC visualization (254 nm) and HPLC PDA tracking (λ ~340–380 nm typical for related chalcones). Use inert atmosphere if nucleophiles or bases are air/moisture sensitive.
Safety and Handling
Item-specific (Product Data)
Storage Conditions: Room temperature
Research Use Note: For research use only
GHS Classification, Signal Word, H-Statements, Pictograms: Not specified for this item; refer to SDS.
General safety guidance (not a substitute for SDS)
Likely hazards for chalcone-like enones include irritation to skin/eyes/respiratory tract; however, no official classification is provided here. Always consult the product SDS before use.
Personal protective equipment: lab coat, safety glasses or face shield, and suitable chemical-resistant gloves (e.g., nitrile). Handle powders in a fume hood to minimize dust inhalation.
Handling considerations: Avoid contact with strong bases or nucleophiles if preserving the enone functionality is required; avoid strong oxidants. Prevent exposure to strong UV light if photochemical stability is a concern for conjugated enones.
First-aid overview (general): In case of skin/eye contact, rinse with water for at least 15 minutes; remove contaminated clothing. If inhaled, move to fresh air. If swallowed, rinse mouth; do not induce vomiting; seek medical attention in all cases as per SDS guidance.
Spill and disposal: Collect solids by gentle sweeping or HEPA vacuum; avoid dust generation. Dispose of according to institutional and local regulations for organic laboratory chemicals.
Fire safety: Treat as a combustible organic solid; use CO2, dry chemical, or foam as appropriate. Combustion may produce CO/CO2 and irritating fumes.
Solvent Selection
Polarity and miscibility (literature/general)
The compound is a conjugated chalcone with multiple methoxy groups and one phenolic OH, yielding low water solubility but good solubility in polar aprotic and moderately polar protic organic solvents (DMSO, DMF, MeOH, EtOH, acetone, EtOAc, CH2Cl2). Toluene and THF are also commonly usable.
For biological assays, DMSO stock solutions (e.g., 10–50 mM) are typical due to high solvating power and compatibility with screening workflows.
Choosing solvents by task (general guidance)
Spectroscopy: Use spectroscopic-grade MeOH/EtOH or acetonitrile for UV–Vis to minimize background and enable observation of π→π* transitions. DMSO-d6 or CDCl3 are typical for NMR; the intramolecular H-bond may shift the OH resonance downfield.
Synthesis: For base-mediated steps or Michael additions, polar aprotic solvents (THF, MeCN, DMF, DMSO) favor reactivity. For electrophilic aromatic substitutions on the methoxy-rich ring, use non-nucleophilic solvents (CH2Cl2, nitromethane) to control selectivity.
Purification: Normal-phase silica gel is common; however, the phenolic OH can tail on silica—adding 0.1–1% Et3N or switching to reverse-phase C18 (water–acetonitrile) can improve band shape.
Quick comparison (general)
DMSO: highest solubility, best for stock solutions; high boiling point complicates removal.
MeCN/EtOAc: balanced polarity for reactions and workups; easy removal.
CH2Cl2: excellent for chromatography and rapid extractions; consider greener alternatives if possible (see Green Alternatives).
Storage and Reconstitution
Item-specific (Product Data)
Storage Conditions: Room temperature
Shipped In: Not specified for this item; refer to CoA/Spec Sheet.
General storage recommendations (guidance; not item specification)
Store tightly sealed in a dry place, protected from excessive light and moisture. For long-term archival, consider desiccation and storage in amber containers to preserve conjugated chromophores.
Avoid prolonged exposure to strong bases or acids during storage to prevent degradation of the enone or deprotection of methoxy groups.
Reconstitution and handling
Prepare stock solutions in dry DMSO, DMF, or alcohols. Filter through 0.22 µm PTFE if particle-free solutions are required.
If repeated use is expected, aliquot stock solutions to minimize freeze–thaw; store aliquots at −20 °C protected from light for extended periods. Allow to equilibrate to room temperature before opening to prevent moisture condensation.
Aqueous solutions are not recommended due to low solubility; if necessary, use co-solvents or inclusion complexes (e.g., cyclodextrins) in research settings.
Stability and specification notes
No stabilizers, shelf-life, or assay specifications are provided here. Where exact limits (water, residual solvents, metal content, UV cutoffs) are required: Not specified for this item; refer to CoA/Spec Sheet.
Structure and Identity
Brief overview: 2-Hydroxy-3,4,5,6-tetramethoxychalcone is a substituted chalcone (α,β-unsaturated aryl ketone) bearing an ortho-phenolic OH on one ring and four methoxy substituents on the other ring.
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Literature/computed identity details (for reference; not item specification)
Core scaffold: chalcone (1,3-diphenyl-2-propen-1-one) with an α,β-unsaturated carbonyl (enone)
Substitution pattern: Ring A contains a 2-hydroxy (ortho to the enone linkage); Ring B contains four methoxy groups at the 3-,4-,5-,6-positions (tetramethoxy). The substitution creates a highly electron-rich B ring and a potential intramolecular H-bond between the 2-OH and the carbonyl oxygen.
Putative molecular formula (based on name): C19H20O6 (literature)
A trans-α,β-unsaturated ketone bridge (–CO–CH=CH–) connects two aromatic rings. One ring features an ortho-phenol capable of six-membered intramolecular H-bonding to the carbonyl; the other ring is densely substituted with four methoxy groups, conferring strong electron-donating character and enhanced conjugation across the enone system.
Synthetic Utility
Functional groups enabling reactivity (literature)
α,β-Unsaturated ketone (Michael acceptor), phenolic OH (orthogonal handle), and four anisole-type methoxy groups (electron donation, directing effects, cross-coupling handles after demethylation to phenols).
Strategic transformations
Flavone/aurone synthesis: 2′-Hydroxychalcones cyclize oxidatively to flavones (e.g., I2/DMSO, PhI(OAc)2) or to aurones under gold/silver catalysis—useful routes to densely oxygenated flavonoids.
Conjugate additions: Install diverse nucleophiles (malonates, nitroalkanes, thiols, amines) 1,4- to the enone, enabling rapid diversification into β-substituted ketones followed by further manipulations (reduction, oxidation, cyclization).
Selective protections: Convert the phenolic OH to ethers/esters to tune reactivity and solubility. Demethylation (BBr3, AlCl3/thiols) can unmask additional phenols from methoxy groups for subsequent coupling (e.g., diaryl ether or biaryl formation).
Redox tuning: Chemoselective hydrogenation (1,4- vs 1,2-) or NaBH4/CeCl3 (Luche) reduction strategies provide access to allylic alcohols or saturated alcohols, guiding synthesis of more complex targets.
Retrosynthetic value
Readily accessed by Claisen–Schmidt condensation between appropriately substituted benzaldehydes and acetophenones; thus, it serves as both a synthetic endpoint and a versatile branching-point intermediate for polyphenolic frameworks.
Target Specificity
Not applicable. This SKU is a small-molecule chalcone and not a biological macromolecule or antibody. No antigen, epitope, isotype, or species reactivity data are relevant. Any biochemical interactions would be context-dependent and are not specified for this item; refer to primary literature for target studies using related chalcones.
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