Licochalcone B - 10mM in DMSO , CAS No.58749-23-8

CAS: 58749-23-8 Cat. No.: L655424 Formula: C₁₆H₁₄O₅ Peso molecolare: 286.28 PubChem CID: 5318999

QUALITÀ & PUREZZA 10mM in DMSO

Storage

Protected from light,Store at -80°C

Shipped In

Dry ice packs + Cold packs

Panoramica

Licochalcone B is an extract from the root of Glycyrrhiza uralensis . Licochalcone B inhibits amyloid β ( 42 ) self-aggregation ( IC 50 =2.16 μM) and disaggregate pre-formed Aβ 42 fibrils, reduce metal-induced Aβ 42 aggregation through chelating metal ionsLicochalcone B inhibits phosphorylation of NF-κB p65 in LPS signaling pathway. Licochalcone B inhibits growth and induces apoptosis of NSCLC cells. Licochalcone B specifically inhibits the NLRP3 inflammasome by disrupting NEK7‐NLRP3 interaction

In Vitro

Licochalcone B (IC 50 : 2.16 μM) inhibits self-mediated Aβ42 aggregation and disaggregates Aβ42 pre-formed fibrils. Licochalcone B (0-12 μM, 48 h) reduces the ROS generation and protects cells from H 2 O 2 -induced cell death in SH-SY5Y cells. Licochalcone B (10 μM, 1 h) inhibits LPS-induced NF-κB activation in RAW264.7 cells. Licochalcone B (10 μM, 1 h) inhibits the LPS-induced phosphorylation of NF-κB p65 at serine 276, and inhibited the expression of TNFα and MCP-1. Licochalcone B (0-20 μM, 24 or 48 h) inhibits human NSCLC cell growth. MCE has not independently confirmed the accuracy of these methods. They are for reference only. Western Blot AnalysisCell Line: RAW264.7 cells Concentration: 10 µM Incubation Time: 1 h Result: Inhibited the phosphorylation of NF-κB at serine 276 but not at serine 536.

In Vivo

Licochalcone B (1-25 mg/kg, oral gavage) alleviates oxidative stress of hepatotoxicity in mice induced by CCl 4. MCE has not independently confirmed the accuracy of these methods. They are for reference only. Animal Model: Mice induced by CCl 4Dosage: 1, 5, 25 mg/kg Administration: Oral gavage. Result: Elevated the levels of SOD and GSH, and reduced the GSSG levels.

IC50& Target:NLRP3

Specifiche

Specifiche e purezza

10mM in DMSO

Meccanismi biochimici e fisiologici

Licochalcone B is an extract from the root of Glycyrrhiza uralensis . Licochalcone B inhibits amyloid β ( 42 ) self-aggregation ( IC 50 =2.16 μM) and disaggregate pre-formed Aβ 42 fibrils, reduce metal-induced Aβ 42 aggregation through chelating metal io

Condizioni di conservazione di stoccaggio

Protected from light,Store at -80°C

Spedito in

Dry ice packs + Cold packs

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Tipo di azione

ACTIVATOR

Nomi e identificatori

Isomeri SMILES

COC1=C(C=CC(=C1O)O)/C=C/C(=O)C2=CC=C(C=C2)O

PubChem CID

5318999

Peso molecolare

286.28

Proprietà chimiche e fisiche

• Punto di infiammabilità (°F): Not applicable
• Punto di infiammabilità (°C): Not applicable

Application Protocols

Item-specific, validated protocols are not provided for this SKU. The following are general, non-binding examples for handling small-molecule standards like prenylated chalcones.

• Preparation of DMSO stock (general):

  • Warm a measured amount of DMSO (amber vial) to 25–37 °C.
  • Add compound to achieve 10–50 mM (as solubility allows); vortex and sonicate briefly. Optional: nitrogen blanket. Filter (0.22 µm PTFE) if particulate remains.

• Dosing into aqueous assays (general):

  • Add stock to buffer with rapid mixing to keep final DMSO at ≤0.1–1% v/v. Include vehicle controls at identical solvent content. Protect plates/tubes from light (foil wrap or amber plasticware).

• HPLC reference standard solution (general):

  • Dissolve to 0.1–1.0 mg/mL in MeOH or ACN; store aliquots at −20 °C to −80 °C, protected from light. Verify stability by periodic injections and peak purity analysis (DAD/MS).

• Solid handling:

  • Work quickly at ambient temperature, minimize exposure to air/light, and promptly return material to cold, dark storage. Use pre-chilled tools where feasible.

These examples are provided as general guidance only. Optimize concentrations/conditions for your specific assay and instrument.

Biological Roles

Item-specific biological data are not provided for this SKU. The following information is general/literature context for prenylated chalcones such as Licochalcone B and is intended for research planning only (no clinical claims).

• Origin and biosynthesis (general):

  • Licochalcone B is reported as a natural product from Glycyrrhiza (licorice) species, arising from the phenylpropanoid/flavonoid biosynthetic pathway. Chalcones are formed by chalcone synthase via Claisen-type condensation, then diversified by prenyltransferases and tailoring enzymes.

• Molecular features relevant to bioactivity (general):

  • The α,β-unsaturated carbonyl can undergo reversible Michael addition with nucleophilic residues (e.g., cysteine) in proteins in vitro, a common motif in electrophile-sensing studies.
  • Phenolic groups contribute to redox chemistry and metal chelation in biochemical assays.

• In vitro assay contexts (general):

  • Used as a reference constituent in phytochemical profiling and as a model prenylated chalcone in enzyme inhibition/ligand-binding screens.
  • Strong UV chromophore simplifies detection in plate-based assays (UV/fluorescence quenching studies) and LC–MS workflows.

Note: Any specific potency, targets, or cellular effects must be derived from primary literature and are assay-dependent. This product is for research use only.

Buffer Applications

This compound is not a buffering reagent and is not typically used to prepare biological buffers.

• Practical note: If Licochalcone B is used in biochemical assays, it is commonly dosed from an organic co-solvent (e.g., DMSO or ethanol) into an existing buffer system (PBS, HEPES, Tris, etc.). Maintain low final co-solvent percentages (commonly ≤0.1–1% v/v) to avoid perturbing buffer capacity or protein stability.

• Tip: Pre-equilibrate the buffer and add the compound stock last with rapid mixing; include equivalent co-solvent in vehicle controls for accurate comparisons.

Green Alternatives

As a solid target compound, “green alternatives” mainly concern solvent choices for dissolution, extraction, and chromatography during handling and analysis.

• Greener solvent substitutions (general guidance):

  • Replace DMF/DMSO (where compatible) with bio-based or lower-toxicity options such as 2-methyltetrahydrofuran (2-MeTHF) for workups and extractions, and ethanol or isopropanol as co-solvents for assay preparations.
  • For normal-phase and flash chromatography, prefer ethyl acetate/heptane over dichloromethane/hexanes where resolution allows.
  • In reversed-phase LC, increase aqueous content and use ethanol instead of acetonitrile when instrument backpressure and resolution permit.

• Tradeoffs to consider:

  • Solubility: chalcones typically dissolve best in polar aprotic solvents; greener alcohols may require warming or higher volumes to achieve target concentrations.
  • Evaporation energy: ethanol and 2-MeTHF can be more energy-intensive to remove compared to acetonitrile or dichloromethane in some setups.

• Small comparison (general):

  • DMSO vs ethanol: DMSO offers higher solubility and stability but is less volatile and may affect bioassays; ethanol is greener and volatile but may limit achievable stock concentrations.
  • Acetonitrile vs ethanol in RP-HPLC: ACN gives lower backpressure and sharper peaks; ethanol is safer/greener but increases viscosity and may reduce resolution.

Adopt solvent-minimization practices: concentrate stocks, aliquot to reduce waste, and use amber glassware to extend solution life.

Pharmaceutical Uses

No pharmacopeial or excipient status is specified for this item; it is supplied strictly for research use only.

General, non-clinical uses in pharmaceutical R&D (literature/practice):

• Analytical reference standard: quantification of licorice-derived constituents in raw materials, extracts, and finished goods during identity/purity testing and stability studies.
• Method development: system-suitability or retention marker in RP-HPLC/UPLC methods targeting prenylated flavonoids.
• Preformulation research: solubility/stability screening in co-solvent systems and evaluation of adsorption to plastics vs glass.

No therapeutic or clinical claims are made for this product.

Physical Properties

Item-specific specifications (for this catalog entry):

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
• Melting point, boiling point, density, refractive index, pKa, logP, UV cutoffs: Not specified for this item; refer to CoA/Spec Sheet.

General/literature context for chalcones and prenylated chalcones (for planning only; verify experimentally):

• Physical state: typically yellow to orange crystalline solids due to extended conjugation.
• Solubility profile: sparingly soluble in water; soluble in polar aprotic organics (DMSO, DMF) and moderately in alcohols/ethyl acetate; solubility improves with mild heating/sonication.
• UV/Vis: conjugated enone shows strong π→π* band in the UVA region (~330–380 nm) and an n→π* shoulder at longer wavelength (literature, chalcone class).
• Stability: phenolic/prenylated chalcones can undergo light-induced isomerization/oxidation; handle under reduced light and inert atmosphere when possible.

Notes for method development (general):

• HPLC/UPLC detection: strong UV response at 280–340 nm; diode-array detection enables peak purity assessment.
• Partitioning: prenylation increases hydrophobicity; expect higher retention in reversed-phase systems versus non-prenylated chalcones. These are literature-based expectations; actual values depend on exact substitution pattern.

Quality and Grades

• Grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
• Appearance: Not specified for this item; refer to CoA/Spec Sheet.

How to interpret quality information (general guidance):

• Research grade vs analytical grade: research grade supports discovery assays and method development; analytical/reference grade emphasizes tight assay purity, low residual solvents, and trace-impurity profiles suitable for quantitation.
• Natural product standards: for LC/GC quantitation, look for assay purity (e.g., HPLC area%), water/solvent content, and impurity fingerprint chromatograms on the CoA.
• UV profile and identity: for chalcones, DAD or UV spectra (λmax in the UVA range) and HRMS/NMR data bolster identity confirmation. If stabilizers are added (rare for solids), they will be declared on the spec/CoA; none are specified for this item.

Batch-specific checks to request/verify:

• Assay (HPLC), residual solvents (GC), water (Karl Fischer), and light-stability notes.
• Retest date and recommended storage after opening (aliquoting, desiccation).

Reaction and Applications

This listing is for Licochalcone B as a research chemical/standard. While not primarily used as a reagent, prenylated chalcones have a reactive α,β-unsaturated carbonyl (Michael acceptor) and phenolic groups, enabling several laboratory applications and transformations.

• Applications in research:

  • Analytical standard: quantitation of licorice-derived constituents in botanicals, foods, and metabolomic studies (HPLC/UPLC–DAD/ESI–MS).
  • Probe molecule: evaluates reactivity of nucleophiles (thiols/amines) toward Michael acceptors in model systems; useful in redox/thiol chemistry assays (general).

• Transformations of the chalcone scaffold (general/literature):

  • Conjugate addition: soft nucleophiles (e.g., thiols, enolates) add at β-position; enables adduct mapping by LC–MS.
  • Cyclizations: intramolecular oxa-/aza-Michael or base/acid-promoted cyclization to flavanones/aurones; oxidative cyclization to flavonols (e.g., Algar–Flynn–Oyamada from appropriately hydroxylated chalcones).
  • Hydrogenation: selective C=C reduction to dihydrochalcones (Pd/C, H2) while retaining carbonyl.
  • Photochemistry: E/Z isomerization and [2+2] photocycloadditions under UV; handle with light protection to avoid unintended changes.

• Practical tips:

  • Protect from light and oxygen to minimize isomerization/oxidation; work under amber light when feasible.
  • For nucleophile-reactivity assays, include internal standards and monitor by time-resolved LC–MS to capture adduct kinetics.
  • Prenylation increases lipophilicity; consider surfactants or co-solvents in aqueous media.

Reaction Conditions

General literature conditions for transforming chalcones (for planning/derivatization; not item-specific specs):

• Hydrogenation to dihydrochalcones:

  • Catalyst: 10% Pd/C (5–10 wt% vs substrate) or Raney Ni; solvent: EtOH, EtOAc, or THF; 1–3 bar H2; 20–25 °C; 1–6 h. Selective C=C reduction achievable, retaining the carbonyl.

• Conjugate additions (Michael):

  • Nucleophiles: thiols, malonates, amines; base: Et3N or DBU (0.1–1.0 eq); solvent: MeCN, MeOH, or DMF; 0–25 °C; minutes to hours. Monitor by LC–MS to avoid overaddition or polymerization.

• Cyclization to flavanones/aurones:

  • Conditions: weak base (K2CO3) or acid (AcOH/H+); solvent: EtOH or MeOH; reflux 2–12 h. o-Hydroxy substitution promotes oxa-Michael closure.

• Algar–Flynn–Oyamada oxidation (to flavonols, if o-hydroxychalcone):

  • Reagents: H2O2/NaOH in EtOH/H2O; 0–25 °C; 1–6 h, then acidic workup. Provides flavonols via oxidative cyclization.

• Photochemical E/Z isomerization:

  • UV-A irradiation (320–380 nm) in degassed MeCN or EtOH; minutes to hours with light shielding for controls. Track by UV/Vis and HPLC.

All parameters above are literature-style guidance for chalcones generally. Optimize for the specific substitution pattern of Licochalcone B and verify by small-scale trials.

Safety and Handling

Item-specific hazard/GHS information for this SKU:

• Signal word: Not specified for this item; refer to SDS.
• Hazard statements (H-codes): Not specified for this item; refer to SDS.
• GHS classification and pictograms: Not specified for this item; refer to SDS.

General laboratory handling guidance for prenylated chalcones (supplemental; consult SDS for authoritative instructions):

• Potential hazards: may cause irritation to eyes/skin/respiratory tract; dust can be irritating. Phenolic compounds and α,β-unsaturated ketones can exhibit sensitization potential in some users; avoid skin contact.
• PPE: lab coat, safety glasses/goggles, and nitrile gloves. Use in a fume hood to minimize inhalation exposure and protect from light.
• Storage incompatibilities: avoid strong oxidizers, strong bases/acids that can induce degradation (e.g., retro-aldol, Michael addition), and light/heat.
• First-aid overview: eye/skin contact—rinse with water for 15 min; remove contaminated clothing. Inhalation—move to fresh air. Ingestion—rinse mouth; seek medical attention. Always follow site SOPs and SDS.
• Spill and disposal: avoid dust generation; collect with dampened inert absorbent. Dispose of as organic laboratory waste per local regulations.
• Special risks: photosensitivity leading to discoloration or potency loss; prepare solutions immediately before use, protect from light, and consider inert gas overlay for long-term stock solutions.

Solvent Selection

This compound is a hydrophobic, prenylated chalcone; dissolution generally follows patterns typical of flavonoids.

• Practical solvent choices (general/literature):

  • Strong solvents for stock solutions: DMSO, DMF (often up to 10–50 mg/mL with warming/sonication).
  • Moderately good: ethanol, methanol, acetonitrile, ethyl acetate.
  • Poor: water and aqueous buffers without co-solvent/surfactant.

• Miscibility/use cases:

  • Biochemical assays: prepare concentrated DMSO stocks (e.g., 10–50 mM) and dilute into aqueous buffers, keeping final DMSO ≤0.1–1% v/v to minimize assay interference (general practice).
  • Chromatography: reversed-phase (C18) with water–acetonitrile or water–methanol; add 0.1% formic acid for LC–MS compatibility.

• Dielectric/polarity context (general): chalcones exhibit moderate-to-high logP; solvent polarity strongly affects retention and recovery from plastics. Prefer glass vials and low-adsorption pipette tips.

• When to choose alternatives:

  • If DMSO is incompatible with your assay, consider ethanol or cyclodextrin-assisted aqueous vehicles.
  • For preparative work, ethyl acetate/hexanes or toluene/EtOAc gradients can be effective, with light protection.

Note: Item-specific solubility is not provided. Verify solubility and stability empirically for your system before scale-up.

Storage and Reconstitution

Item-specific instructions (from Product Data):

• Storage: Protect from light; store at −80 °C.
• Shipping: Dry ice packs + cold packs.

Best practices (general, to maximize stability):

• Upon receipt: keep sealed and cold. Allow container to equilibrate to room temperature in a desiccator before opening to prevent moisture condensation.
• Aliquoting: divide into single-use, light-protected aliquots (amber glass vials or foil-wrapped microtubes) to minimize freeze–thaw and headspace oxygen.
• Atmosphere: if feasible, backfill vials with inert gas (N2/Ar) before re-freezing to reduce oxidative degradation of the enone and prenyl groups.
• Reconstitution: prepare concentrated stocks in dry DMSO or ethanol immediately prior to use. Mix thoroughly (vortex/sonicate), and filter through PTFE (0.2 µm) if needed. Record solvent, lot, and preparation date.
• In-use stability: keep solutions on ice and protected from light during experiments. For longer-term storage of solutions, prefer −20 to −80 °C in amber, crimp-sealed vials with minimal headspace; verify integrity by HPLC before critical use.

Note: No item-specific solubility, stabilizers, or retest dates are provided here—refer to the CoA/Spec Sheet and SDS for lot-specific guidance.

Structure and Identity

Licochalcone B is a prenylated chalcone (flavonoid-type) featuring an α,β-unsaturated ketone linking two phenyl rings.

• Item-specific identifiers:

  • CAS: 58749-23-8
  • SKU: L655424
  • Category: Small molecules and compound libraries (研究/实验用)
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.
  • InChIKey: 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 class and features (general/literature):

  • Core scaffold: chalcone (1,3-diaryl-2-propen-1-one) with an E-configured enone (–CO–CH=CH–) conjugated to two aromatic rings (A and B).
  • Typical substituents: phenolic OH groups and an isoprenyl (or related) side chain on one ring, contributing to lipophilicity and UV activity.
  • Functional groups: α,β-unsaturated ketone (Michael acceptor), phenols, allylic/terpenoid substituent.

• 2D structure described in words (general): an A-ring bearing phenolic substituents is connected via a trans-enone linker to a B-ring; one ring typically carries a prenyl unit at the ortho/para positions. The conjugated system imparts strong UV absorption around 330–380 nm (literature, chalcones).

Synthetic Utility

Although Licochalcone B is primarily a target compound/standard, the chalcone scaffold provides versatile reactivity useful for derivatization and SAR studies.

• Key functional groups and reactivity (general):

  • α,β-Unsaturated ketone (enone): undergoes Michael additions with soft nucleophiles (thiols, malonates), selective hydrogenation (to dihydrochalcones), and photochemical E/Z isomerization.
  • Phenolic OH groups: amenable to etherification/esterification, O-alkylation/acylation for prodrug-like modifications or protecting-group strategies.
  • Prenyl substituent: can participate in electrophilic additions, oxidative rearrangements, or serve as a handle for cross-metathesis (if terminal) in model systems.

• Named transformations (literature):

  • Algar–Flynn–Oyamada oxidation of o-hydroxychalcones to flavonols.
  • Base/acid-catalyzed intramolecular cyclization to flavanones/aurones.
  • Boron- or organocatalyzed Michael additions to enones for stereocontrolled adducts.

• Retrosynthetic value:

  • Accessed via Claisen–Schmidt condensation of appropriately substituted acetophenone and benzaldehyde derivatives, followed by selective prenylation; offers a platform for generating analog libraries by varying aryl substitution, enone geometry, and side-chain patterning.

Target Specificity

Not applicable for this product type. Licochalcone B is a small-molecule natural product, not an antibody or affinity reagent.

• Item-specific target/epitope, clone, isotype, or species reactivity: Not specified for this item; refer to CoA/Spec Sheet if any biochemical target testing is provided in future lots.

Domande frequenti

How should this product be stored?

Store at ?80 °C, protected from light. The material is light-sensitive — keep it in its original opaque or amber container.

How is this product shipped?

This product ships frozen with dry ice and cold packs. Unpack on arrival and transfer it to the storage condition stated above; handle dry ice with insulated gloves in a ventilated area.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 58749-23-8, the molecular formula is C16H14O5, and the molecular weight is 286.28 g/mol.

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.