≥98% per flussi di lavoro cromatografici e analitici sensibili che richiedono un'interferenza minima della linea di base.
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Stoccaggio e spedizione
Protected from light,Store at -20°C Spedizione Ice chest + Ice pads. Consultare il COA specifico del lotto per le specifiche esatte.
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Documenti di qualità
SDS, COA, scheda tecnica e scheda delle specifiche disponibili per il download. COA specifico del lotto accessibile tramite ricerca per numero di lotto.
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Prova documentale
Citato in 0 pubblicazioni peer-reviewed su cromatografia, sintesi organica e reazioni di accoppiamento incrociato.
Panoramica
Echinatin disturb the mitochondrial energy transfer reactions and membrane permeability, at a low concentration cause deterioration of respiratory control and oxidative phosphorylation of isolated rat liver mitochondria, inhibits DNP-ATPase activity while stimulating range latent ATPase activity. Echinatin has significant antioxidant activities, it shows strong scavenging activity toward the ABTS + radical, it also dose-dependently inhibits LPS induced reactive oxygen species (ROS) production in RAW 264.7 cells and inhibits the production of nitric oxide (NO), interleukin-6 (IL-6) and prostaglandin E2 (PGE2) in LPS-induced macrophage cells.
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
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.
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Recensioni
Recensioni dei clienti
Application Protocols
No validated immunoassay or biochemical kit protocols are supplied for this item.
General research-use workflows where chalcones like echinatin are commonly employed:
Preparation of DMSO stock solutions (e.g., 10–50 mM) under low light; sterile filtration (0.22 µm PTFE) if required for cell-based assays.
LC–UV/LC–MS reference standard use: Prepare calibration curves across expected concentration range; store aliquots at −20 °C protected from light; verify peak purity at multiple wavelengths (e.g., 254/280/340 nm).
Solubility/stability screens: Evaluate in assay-relevant media with vehicle controls; monitor precipitation and recovery by LC after defined incubation.
For any application requiring validated parameters (e.g., extinction coefficient, response factors), consult the CoA/Spec Sheet or establish in-house under your method conditions.
Biological Roles
Echinatin is reported in the literature as a plant-derived chalcone from Glycyrrhiza (licorice) species, belonging to the flavonoid biosynthetic pathway.
Biosynthetic context (general): Chalcones arise via chalcone synthase (CHS) from p‑coumaroyl‑CoA and malonyl‑CoA, serving as central intermediates en route to flavanones, isoflavonoids, and related phenylpropanoids.
Physicochemical traits relevant to biology (general): Conjugated enone and phenolic substituents contribute to UV absorption (plant photoprotection/pigmentation) and redox activity typical of polyphenols.
Laboratory study roles (research use only):
Reference standard in phytochemical profiling of licorice extracts by LC–UV/LC–MS.
Tool compound for studying chalcone reactivity with nucleophilic biomolecules (e.g., thiol adduction) in chemical biology assays.
Component in natural product libraries for screening structure–activity relationships within flavonoid/chalcone chemotypes.
No medical or clinical claims are made; any biological discussion here is limited to general, literature-based roles of chalcone-type natural products and the use of reference materials in research and analytical method development.
Buffer Applications
Echinatin is not a buffering agent and is not typically used to prepare aqueous buffer systems.
Practical note: If echinatin must be introduced into buffered media for assays, prepare a concentrated DMSO or ethanol stock and dilute into the buffer with vigorous mixing, keeping the final organic cosolvent low (≤0.1–0.5% v/v) to avoid precipitation and biological confounding.
For actual buffer preparation and pH control, choose dedicated buffering systems (e.g., phosphate, HEPES, Tris) appropriate to your application.
Green Alternatives
While echinatin is a target analyte/compound rather than a process solvent, greener choices can be made for its handling, purification, and transformations.
Dissolution/handling (general):
Prefer ethanol or ethyl acetate over DMF/DMSO when feasible for workup and crystallization; for assay stocks, DMSO remains common but minimize volumes and consider PEG400/ethanol cosolvents when compatible.
Reaction media (general):
Use 2-methyltetrahydrofuran (2-MeTHF) or cyclopentyl methyl ether (CPME) instead of toluene/THF when appropriate for reductions or conjugate additions.
Aqueous micellar catalysis (e.g., TPGS-750-M) can enable cross-coupling or conjugate additions with reduced organic solvent usage.
Purification:
Employ reverse-phase flash/LC with water–acetonitrile gradients; replace acetonitrile with ethanol or isopropanol where chromatographic performance permits.
Comparison (general guidance):
DMF/DMSO: excellent solubility; poor EHS profile; difficult to remove.
Ethanol/2‑MeTHF: renewable, lower toxicity; may require longer dissolution times or higher temperature.
These are literature-based green chemistry considerations for chalcone-class compounds; assess compatibility with your specific protocol and purity targets.
Pharmaceutical Uses
No pharmacopeial or excipient status is provided for this item; echinatin is offered for research use only.
Typical research/formulation contexts (general):
Analytical reference standard for quality control of botanical raw materials and extracts (e.g., licorice) by HPLC/UPLC.
Tool compound in pre-formulation solubility and stability studies of chalcone chemotypes, focusing on solvent screening, pH stability, and photostability (research only).
Regulatory note: Without pharmacopeial monograph or GMP documentation, material is not intended for human or veterinary use or for inclusion in commercial drug products.
Always consult internal QA policies before using research-grade materials in any regulated workflow.
Physical Properties
Item-specific physicochemical specifications have not been provided for this catalog entry.
Appearance: Not specified for this item; refer to CoA/Spec Sheet. (product data)
Molecular weight (spec): Not specified for this item; refer to CoA/Spec Sheet. (product data)
Melting point, boiling point, density, refractive index: Not specified for this item; refer to CoA/Spec Sheet.
Solubility (general, literature for chalcones):
Low aqueous solubility at neutral pH due to hydrophobic aromatic framework; solubility can improve in basic media via phenolate formation.
Readily soluble in polar aprotic organics (DMSO, DMF) and moderately in ethanol/methanol; often prepared as DMSO stock solutions for bioassays.
UV/Vis (general, literature): Conjugated chalcones typically show λmax ~330–380 nm with an additional band in the 200–280 nm region; exact values depend on substitution.
LogP/pKa (general, literature): Chalcones are moderately lipophilic (logP commonly 2–4) with phenolic pKa values typically ~8–10 depending on substitution. These are general ranges for chalcone-class compounds, not item-specific specifications.
Note: For assay-critical parameters (water content, residual solvents, exact solubility, extinction coefficients), consult the item’s CoA/Spec Sheet.
Quality and Grades
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Guidance on interpreting quality (general):
Research grade phytochemicals/natural products are typically characterized by 1H/13C NMR, HPLC/UPLC purity, MS, and sometimes optical rotation. For chalcones, HPLC at multiple wavelengths (e.g., 254/280/340 nm) helps confirm purity given strong UV absorption.
If an HPLC grade is offered for analytical applications, expect tight control of UV-absorbing impurities and residual solvents; if a bioactive screening grade is offered, expect emphasis on chemical purity and identity, with documentation suitable for SAR/HTS.
Stabilizers: Not specified for this item; refer to CoA/Spec Sheet. Many phenolic chalcones do not require stabilizers but benefit from light protection and inert storage.
What to check on the CoA/Spec Sheet for this item:
Exact purity percentage and analytical method/wavelengths used.
Identity confirmation data (NMR/MS/HRMS; retention time/index).
Residual solvent and water content (if reported).
Storage and re-test period; any special notes on photostability.
For quantitative analytical use (e.g., as a reference standard in natural products QC), use lots supplied with full chromatographic trace and identity data.
Reaction and Applications
Research-use contexts for echinatin typically align with chalcone chemistry and natural products analytics.
Analytical/standards:
Reference standard for licorice-derived flavonoids in herbal identity testing and metabolomics (LC–UV/LC–MS). Detection often at near‑UV wavelengths due to the conjugated enone (literature, general).
Reactivity (general chalcone behavior):
Michael acceptor: undergoes 1,4-conjugate addition with soft nucleophiles (thiols, amines, stabilized carbanions), enabling adduct formation and probe derivatization.
Carbonyl chemistry: participates in imine/enamine-mediated transformations; can be reduced (NaBH4 catalytic with CeCl3, or transfer hydrogenation) to dihydrochalcones; full hydrogenation saturates the double bond.
Cyclizations: base- or acid-promoted intramolecular cyclization to flavanones/aurones depending on substitution and conditions (literature).
Electrophilic aromatic substitution on phenolic rings is directed by –OH/–OMe groups; O-alkylation/acylation affords protected derivatives for SAR.
Practical tips:
Light sensitivity: protect from light during reactions and purification.
Avoid strong base for extended periods if the chalcone is base-labile; monitor by TLC/LC.
For bioassay stocks, filter-sterilize DMSO solutions (0.22 µm PTFE) to remove particulates; verify stability over intended assay period.
Manufacturer applications: Not specified in product data; the above expands on common research uses of chalcone-type standards (literature, general).
Reaction Conditions
Typical literature conditions applicable to chalcone scaffolds (general guidance; not item-specific specifications):
Conjugate (Michael) additions:
Nucleophiles: thiols/amines/malonates; bases such as Et3N, DBU, or organocatalysts; solvents DMSO, MeCN, alcohols; 0–50 °C, 1–24 h.
For stereocontrol, chiral secondary amines or phase-transfer catalysts may be used.
Reductions:
Chemoselective C=C reduction: H2 (1–3 atm) with Pd/C or Pt/C in EtOH/EtOAc at rt–50 °C; hours.
Conjugate hydride: NaBH4 with CeCl3 (Luche-type), i‑PrOH/MeOH, 0–25 °C; minutes to hours.
Epoxidation of enone:
mCPBA or peracetic acid in DCM at 0–25 °C; 1–3 h; followed by nucleophilic opening.
Cyclizations to flavanones/aurones:
Base-promoted (K2CO3/NaOH) in EtOH or DMF, 50–100 °C; or Lewis acids (AlCl3, BF3·OEt2) at 0–25 °C; monitor by LC/TLC due to potential side reactions.
Protection of phenols (if present):
Benzylation (BnBr, K2CO3, acetone/DMF) or silylation (TBSCl, imidazole, DMF) at 0–25 °C.
Yields are highly substrate- and substitution-dependent; consult primary literature for conditions tailored to echinatin specifically. Protect from light throughout to limit isomerization/degradation.
Safety and Handling
GHS classification, signal word, pictograms, H-statements: Not specified for this item; refer to SDS for authoritative safety information.
Storage conditions (product data): Store at −20 °C, protected from light. Shipments are made in ice chest with ice pads to maintain a cold chain.
Stability considerations (general): Polyphenolic chalcones can be sensitive to prolonged light exposure (photoisomerization, oxidation) and strong bases/acids; minimize repeated freeze–thaw and exposure to air/light.
Incompatibilities (general): Strong oxidizers; strong bases/acids may lead to degradation (retro-Claisen–Schmidt, aldol reactions) or phenolate formation with color changes.
Handling/PPE (good laboratory practice): Use in a fume hood; wear lab coat, nitrile gloves, and safety glasses. Avoid inhalation of dust and contact with skin/eyes. Prevent aerosol or dust formation.
First aid (overview; defer to SDS):
Inhalation: Move to fresh air; seek medical attention if symptoms occur.
Skin/eye contact: Rinse with water for several minutes; remove contaminated clothing; obtain medical advice if irritation persists.
Ingestion: Rinse mouth; seek medical attention.
Waste: Dispose of in accordance with institutional and local regulations for organic laboratory waste. Avoid release to the environment.
Always consult the product’s SDS for complete hazard, toxicological, and regulatory details.
Solvent Selection
Echinatin, as a chalcone-type polyphenolic compound, is generally hydrophobic with limited water solubility at neutral pH.
Polarity/miscibility (general, literature for chalcones):
Highly soluble in DMSO and DMF; good solubility in ethanol/methanol; limited in acetonitrile; poor in water unless basified.
Solubility often improves in mildly basic aqueous media via phenolate formation, but this may alter reactivity and assay outcomes.
Practical choices by application:
Bioassays/cell studies: Prepare concentrated DMSO stocks (e.g., 10–50 mM) and dilute into media to ≤0.1–0.5% DMSO final, ensuring vehicle controls.
Chromatography: Reverse-phase LC typically uses water–acetonitrile (or methanol) with 0.1% formic acid for improved peak shape; detection at 280–360 nm is common.
Synthesis/derivatization: Use polar aprotic solvents (DMF/DMSO/MeCN) or alcohols depending on transformation (O-alkylation, acylation, conjugate addition).
Comparison (general):
DMSO: maximal solubilization; hygroscopic; high boiling; good for stocks.
Ethanol/methanol: greener and volatile; may require warming/sonication; can participate in reactions under acidic/basic conditions.
Acetonitrile: LC-friendly; moderate solubility for many chalcones; low viscosity.
Note: Item-specific solubility has not been established here; confirm experimentally or consult the CoA/Spec Sheet.
Storage and Reconstitution
Storage (product data): Store at −20 °C and protect from light. Shipments are made in an ice chest with ice pads to maintain low temperature.
Container and atmosphere (general best practice): Use amber vials or wrap in foil; purge headspace with inert gas (N2/Ar) after opening to limit oxidation. Keep desiccated.
Reconstitution (general):
Prepare concentrated stock solutions in anhydrous DMSO (common) or ethanol. Typical working stocks: 10–50 mM in DMSO (literature/good practice). Mix by gentle warming (≤40 °C) and sonication if needed.
For aqueous use, dilute stock into buffer/media with vigorous mixing; maintain low final organic content to avoid precipitation (≤0.1–0.5% v/v typical in cell assays).
Aliquoting: Divide into single-use aliquots to avoid repeated freeze–thaw; store aliquots at −20 °C in the dark.
Stability: Item-specific stability data are not provided. Monitor integrity by HPLC/LC–MS periodically; discard if significant decomposition, discoloration, or precipitation is observed.
All directions above are intended for research use only. For lot-specific guidance (e.g., maximum concentration, solubility limits, re-test date), refer to the CoA/Spec Sheet.
Structure and Identity
Echinatin is a chalcone-type flavonoid (open-chain α,β-unsaturated aryl ketone) commonly reported from Glycyrrhiza (licorice) species. As a chalcone, it features two aromatic rings (A and B) connected by a three‑carbon enone linker (Ar–CO–CH=CH–Ar), typically bearing phenolic and/or methoxy substituents.
CAS: 34221-41-5 (product data)
PubChem CID: 6442675 (product data)
InChIKey: Not specified for this item; refer to CoA/Spec Sheet. (product data field not provided in full)
SMILES: Not specified for this item; refer to CoA/Spec Sheet. (product data)
Molecular formula: Not specified for this item; refer to CoA/Spec Sheet. (product data)
Molecular weight: Not specified for this item; refer to CoA/Spec Sheet. (product data)
Structural features (general, literature):
Core scaffold: chalcone (1,3-diaryl-2-propen-1-one) with an α,β-unsaturated carbonyl (Michael acceptor).
Functional groups: conjugated enone; phenolic –OH groups are often present on one or both rings; methoxy substituents may occur depending on substitution pattern (literature, general chalcones).
2D description: ring A (often resorcinol-type) joined via enone to ring B (often para‑substituted); planarity favored by conjugation, enabling strong UV absorbance in near-UV region (literature, general).
Synthetic Utility
From a synthetic perspective, echinatin embodies the chalcone 1,3‑diaryl‑2‑propen‑1‑one motif, offering multiple handles for derivatization and scaffold modification (literature, general):
α,β-Unsaturated carbonyl:
Michael additions with thiols, amines, malonates, and enolates to generate β‑substituted ketones and probe conjugates.
Selective hydrogenation to dihydrochalcones; further reduction affords diarylpropanones.
Epoxidation (e.g., peracids) followed by ring opening to access vicinal amino/oxy derivatives.
Aromatic phenols/methoxy groups (typical for chalcones):
O‑alkylation/acylation for protection or to tune lipophilicity/solubility.
Electrophilic substitutions directed by phenolic activation; cross-couplings possible if halogen handles are present after prior functionalization.
Scaffold remodeling:
Intramolecular cyclization to flavanones/aurones under base or Lewis acid catalysis, enabling access to related flavonoid subclasses for SAR libraries.
As a building block/standard, echinatin can seed small focused libraries via late-stage diversification on the phenolic positions or the enone. When used as a starting material, control of E/Z isomerization of the enone and protection of phenols (if present) may be required to achieve chemoselectivity.
Target Specificity
This product is a small-molecule chalcone, not an antibody or affinity reagent. No target/epitope specificity, isotype, or species reactivity applies.
Target specificity data: Not applicable for this compound type.
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