Licochalcone C - 10mM in DMSO , CAS No.144506-14-9

CAS: 144506-14-9 Cat. No.: L656638 Formula: C₂₁H₂₂O₄ Peso molecolare: 338.4 PubChem CID: 9840805

QUALITÀ & PUREZZA 10mM in DMSO

Storage

Protected from light,Store at -80°C

Shipped In

Dry ice packs + Cold packs

Panoramica

Licochalcone C could inhibit α-glucosidase , with IC 50 s of <100 nM and 92.43 μM for α-glucosidase and protein tyrosine phosphatase 1B (PTP1B), respectively.

In Vitro

Licochalcone C could inhibit α- glucosidase, with IC50s of <100 nM and 92.43 μM for α- glucosidase and PTP1B, respectively. It is also indicated that Licochalcone C induces T24 cell apoptosis in a concentration‑dependent manner. Licochalcone C treatment reduces the levels of the anti‑apoptotic mRNAs (Bcl-2, Bcl-w and Bcl-XL) and increases expression of the pro-apoptotic mRNAs (Bax and Bim). The Bcl-2 family inhibitor (ABT-737) reduces apoptosis induced by licochalcone C in T24 cells. MCE has not independently confirmed the accuracy of these methods. They are for reference only.

IC50& Target:IC50: <100 nM (α-glucosidase), 92.43 μM (PTP1B)

Specifiche

Specifiche e purezza

10mM in DMSO

Meccanismi biochimici e fisiologici

Licochalcone C could inhibit α-glucosidase , with IC 50 s of <100 nM and 92.43 μM for α-glucosidase and protein tyrosine phosphatase 1B (PTP1B), respectively.

Condizioni di conservazione di stoccaggio

Protected from light,Store at -80°C

Spedito in

Dry ice packs + Cold packs

Questo prodotto richiede spedizione a catena fredda. I servizi di terra e altri servizi economici non sono disponibili.

Tipo di azione

INHIBITOR

Nomi e identificatori

Isomeri SMILES

CC(=CCC1=C(C=CC(=C1OC)/C=C/C(=O)C2=CC=C(C=C2)O)O)C

PubChem CID

9840805

Peso molecolare

338.4

Proprietà chimiche e fisiche

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

Application Protocols

No vendor-validated application protocols are provided for this item. The following are general, non-binding suggestions for small-molecule handling in common research contexts.

• Stock preparation:
  • Weigh quickly under low light. Dissolve in dry DMSO to prepare a 10–50 mM stock. Vortex and, if needed, brief sonication. Filter (0.22 μm PTFE) for analytical work.
• Cell-based assays (general):
  • Dilute DMSO stock into pre-warmed media to achieve final DMSO ≤0.1–0.5% v/v. Include vehicle controls and, for electrophilic compounds, thiol-quenching controls where relevant.
  • Monitor precipitation visually; if turbidity occurs, reduce concentration or use solubilizing aids compatible with the assay.
• Enzymatic/biochemical assays:
  • Use assay buffer with 0.01–0.05% nonionic surfactant if nonspecific adsorption is suspected. Maintain constant organic content across controls/samples.
• Analytical standard use:
  • Prepare calibration solutions in MeOH or MeCN (with 0.1% formic acid if LC–MS). Store aliquots at −20°C, protected from light; verify stability per your method.

These guidelines are illustrative only. Optimize conditions for your specific system and consult the item’s CoA/SDS for restrictions. For research use only.

Biological Roles

Context from the natural products literature (general background; not item-specific claims):

• Source and biosynthesis: Licochalconce-type compounds are prenylated chalcones occurring in Glycyrrhiza (licorice) species. They arise via the phenylpropanoid/flavonoid pathway, where chalcone synthase condenses p-coumaroyl-CoA with malonyl-CoA units to give naringenin chalcone-like intermediates; downstream tailoring (prenylation, O-methylation, oxidation) yields distinct licochalcones.
• Chemical ecology: Prenylated chalcones serve as phytoalexins, contributing to plant defense against microbes and herbivores (literature, flavonoid role). The prenyl group enhances lipophilicity, membrane association, and interactions with biological membranes/proteins.
• Biophysical/biochemical features:
  • The α,β-unsaturated carbonyl (enone) can act as a soft electrophile toward cysteine thiols in proteins, enabling covalent probe behavior in chemoproteomics workflows (general electrophile chemistry).
  • Phenolic groups contribute to metal-chelation and radical-scavenging capacity in standard antioxidant assays (DPPH/ABTS) used for comparative characterization of flavonoids (assay context; not a performance claim for this item).
• Analytical biomarkers: Licochalcones are used as characteristic markers for authentication and standardization of licorice-derived materials in research settings.

Note: The above describes typical biological roles of the compound class. No therapeutic or clinical claims are made. Use this product strictly for research and analytical applications.

Buffer Applications

This product is not a buffering agent and is not typically used to prepare biological or analytical buffers.

Practical guidance:

• For aqueous assays involving Licochalcone C, first dissolve in a miscible organic co-solvent (commonly DMSO or ethanol) to make a concentrated stock, then dilute into the desired buffer (e.g., PBS, HEPES, Tris) while limiting the final organic content (typically ≤0.1–0.5% v/v) to maintain assay compatibility.
• Consider adding nonionic surfactants (e.g., 0.01–0.1% Tween 80) or cyclodextrins if precipitation occurs upon dilution. Validate that additives do not interfere with your readout.

For routine buffer recipes and pH ranges, refer to standard buffer tables; Licochalcone C does not serve as a pH buffer.

Green Alternatives

While the compound itself is fixed, greener choices can be made in handling, purification, and analysis.

Greener solvent strategies (compared to conventional choices):

• Dissolution for stocks:
  • Preferred: ethanol (anhydrous, pharm/analytical grade) when assay-compatible.
  • Alternative: DMSO remains common but has higher environmental persistence; minimize volumes and collect for proper waste handling.
• Chromatography:
  • Replace acetonitrile with ethanol/water gradients where method robustness allows (increased viscosity may affect backpressure; validate).
  • Use ethyl acetate/heptane in place of dichloromethane/hexane for normal-phase purification when resolution is sufficient.
• Workup and crystallization:
  • Favor EtOAc, isopropanol, and methyl tert-butyl ether (MTBE) over chlorinated solvents when feasible.

Comparison (general):

• DCM vs EtOAc: EtOAc is less toxic, biodegradable, and has favorable EHS profile; may require adjusted eluent strength.
• MeCN vs EtOH/H2O: EtOH is renewable and safer; expect changes in selectivity and detector baselines; PDA compatibility remains strong for chalcones.

Operational practices:

• Scale experiments to minimize solvent usage.
• Recover and recycle solvents (rotary evaporation with appropriate traps; in-house solvent recycling systems).
• Use solid-phase extraction (SPE) to reduce preparative LC solvent volumes for routine cleanups.

All method changes should be validated for recoveries, purity, and stability of Licochalcone C.

Pharmaceutical Uses

No excipient or pharmacopeial status is provided for this item, and it is supplied strictly for research use only.

Research/manufacturing context (non-clinical):

• Reference standard: Can be used to establish identity and content of licochalcone components in licorice-derived research materials (e.g., method development/validation in HPLC–PDA–MS).
• Process development studies: Useful in pre-formulation research exploring solubilization strategies for hydrophobic phenolic compounds (co-solvents, cyclodextrins, amorphous dispersions) strictly for lab-scale investigations.
• Forced-degradation and stability-indicating methods: The conjugated enone/phenolic motifs provide clear degradation pathways (oxidation, isomerization, Michael addition), enabling development of stability-indicating analytical methods in a research/QC environment.

Important: This product is not approved as a drug substance, excipient, or dietary ingredient. Do not use for human or veterinary applications. No clinical or therapeutic claims are made.

Physical Properties

Only limited item-specific physicochemical data are provided for this SKU. Where values are not listed below, consult the CoA/Spec Sheet.

Item-specific:

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

General/literature characteristics for licochalcone-type chalcones (for context only):

• Physical state/Color: typically yellow to orange-yellow solids due to extended conjugation (literature, chalcone class).
• Solubility: sparingly soluble in water; soluble in organic solvents such as DMSO, DMF, ethanol, methanol, acetone, ethyl acetate (literature, class behavior). For assay use, high-concentration DMSO stocks (e.g., 10–50 mM) are commonly prepared (general practice).
• UV–Vis: conjugated chalcones often show strong π→π* absorbance in the near-UV with λmax commonly in the ~330–380 nm range and an additional band at ~240–280 nm (literature, class behavior; not a specification for this item).
• LogP: prenylated chalcones are generally lipophilic (literature trend), supporting membrane permeability in cell-based assays; exact logP for Licochalcone C is not provided here.

Do not treat these literature descriptions as specifications. For quantitative parameters (mp, purity, water content, UV cutoff, residue on ignition, metal limits), refer to the CoA/Spec Sheet for this SKU.

Quality and Grades

Item-specific quality indicators provided:

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

Guidance on interpreting quality for small-molecule standards:

• Research grade/reference standard: Typically emphasizes identity confirmation (NMR/HRMS), purity by HPLC/UPLC, and controlled storage/handling to preserve integrity. Low residual solvents and well-characterized chromatographic behavior are preferred for quantitative work.
• HPLC assay and chromatographic purity: For bioassay or analytical use, purity ≥95% is commonly targeted in the field (literature expectation). Absence of closely eluting isomers is important for clean quantitation.
• Identity confirmation: 1H/13C NMR, HRMS/ESI-MS, and optionally UV–Vis profile for chalcones. If chiral centers are absent (typical for chalcones), no chiral assay is usually required; however, E/Z geometry of the enone can be assessed by NMR coupling constants.
• Stabilizers: None specified for this item. If stabilizers are present in a given lot, they will be disclosed on the CoA; stabilizers can subtly impact UV response and bioassays and should be accounted for in method development.

Recommendation: Use the lot-specific CoA/Spec Sheet for definitive purity, chromatographic method, and acceptance criteria appropriate to your application (analytical standard vs. screening compound).

Reaction and Applications

This product is typically deployed as a natural-product reference standard and as a screening-library member rather than as a bulk reagent. Common research applications include:

Analytical and screening uses:

• Reference standard for profiling/licorice extract characterization by HPLC/UPLC–PDA–MS. The conjugated chalcone core yields distinct UV absorbance suitable for PDA detection (literature, chalcone class behavior).
• Tool compound for phenotypic or biochemical screening panels focused on reactive Michael acceptors (α,β-unsaturated ketones). Appropriate controls are essential to differentiate target-based effects from general electrophile reactivity.
• Calibration/retention marker in metabolomics workflows investigating prenylated flavonoids.

Chemical reactivity context (for derivatization or SAR exploration):

• Michael acceptor chemistry: undergoes 1,4-addition with soft nucleophiles (thiols, amines) under mild base or catalysis (literature, chalcones).
• Cyclizations: base- or acid-promoted intramolecular cyclization to flavanones/aurones and related scaffolds; useful for accessing analogs in SAR.
• Hydrogenation/reduction: selective 1,4- or 1,2-reduction of the enone to generate dihydrochalcones or allylic alcohols (e.g., NaBH4/CeCl3 for conjugate control; catalytic hydrogenation for global reduction; literature guidance).
• O-alkylation/acylation: phenolic groups can be protected or diversified (e.g., methylation/benzylation) to modulate solubility and stability.

Practical tips:

• Prepare fresh solutions shortly before use; phenolic enones may slowly degrade via oxidation/Michael addition during prolonged storage in solution.
• Minimize light and air exposure; use amber vials and inert headspace for long incubations.

Reaction Conditions

General literature conditions relevant to chalcone scaffolds (for derivatization and method development; not item-specific specifications):

• Conjugate (Michael) additions:
  • Solvents: MeOH, EtOH, acetonitrile, THF, or DMF; often under mild base (Et3N, DBU) or with thiols under neutral conditions.
  • Temperature: 0–60°C depending on nucleophile; reaction times from 0.5–24 h.
  • Catalysis: Organocatalysts (secondary amines, imidazoles) or Lewis acids (ZnCl2, InCl3) can accelerate additions.
• Reduction of the enone:
  • 1,4-Reduction: H2 (1–3 atm) over Pd/C or Pt/C in EtOH/EtOAc at rt–40°C; 1–6 h to dihydrochalcones.
  • 1,2-Reduction: NaBH4/CeCl3 (Luche conditions) in MeOH at 0–25°C yields allylic alcohols with minimal conjugate reduction.
• Cyclization to flavanones/flavones:
  • Base-promoted (NaOH/K2CO3 in ethanol or aqueous ethanol) at 25–60°C to effect intramolecular o-phenoxide addition where ortho-OH is present.
  • Oxidative cyclization: I2/DMSO or hypervalent iodine reagents (PIDA/PIFA) in MeCN/CH2Cl2 at 0–25°C.
• O-Alkylation/Acylation:
  • Conditions: K2CO3/DMF or NaH/THF for alkylations (rt–40°C); acylations with acyl chlorides/anhydrides in pyridine or with DMAP catalysts.

Analytical method development:

• RP-HPLC: C18, 30–60% MeCN or MeOH in water (0.05–0.1% formic acid), 1 mL/min (analytical scale), λmonitor 330–380 nm plus 254 nm (literature for chalcones).
• Stability checks: subject to light/air; include amberware and minimal headspace. Evaluate solution stability over 24–72 h at assay temperature.

These conditions are provided as general guidance for chalcone chemistry and should be optimized for Licochalcone C’s specific substitution pattern.

Safety and Handling

Hazard classification details specific to this item are not provided in the product data.

Item-specific safety data:

• GHS Classification: Not specified for this item; refer to SDS.
• Signal Word: Not specified for this item; refer to SDS.
• H-Statements: Not specified for this item; refer to SDS.
• Pictograms: Not specified for this item; refer to SDS.

General laboratory handling (good practice for hydrophobic phenolic chalcones):

• PPE: wear lab coat, safety glasses, and appropriate gloves (e.g., nitrile). Avoid inhalation of dust and contact with skin/eyes. Handle powders in a fume hood or ventilated enclosure to minimize aerosolization.
• Light sensitivity: store and handle with protection from light (item-specific instruction). Use amber vials and minimize exposure during weighing and solution prep.
• Incompatibilities: avoid strong oxidizers and strong bases/acids during storage; phenolic/α,β-unsaturated ketones may undergo base-catalyzed degradation or Michael addition with nucleophiles (general chemistry caution).
• Hygroscopicity: many natural product solids are not strongly hygroscopic, but minimize moisture exposure to preserve material integrity; recap promptly and use desiccation if possible.
• First aid (overview; defer to SDS): rinse with water for skin/eye contact, remove contaminated clothing, and seek medical attention if irritation persists. If inhaled, move to fresh air. If ingested, rinse mouth; do not induce vomiting; obtain medical advice.

Always consult the product’s SDS for authoritative and current safety information. For research use only.

Solvent Selection

For Licochalcone C and related prenylated chalcones, solvent choice is driven by hydrophobicity and phenolic functionality.

• Polarity class: moderately to strongly hydrophobic polyphenolic enone (literature, class behavior).
• Preferred solvents for stock solutions:
  • DMSO (analytical/spectrophotometric grade) — excellent solubilizing power; compatible with most bioassays at ≤0.1–0.5% v/v in final media.
  • DMF — strong solvent; consider toxicity in biological systems.
  • Ethanol or methanol — good for analytical dilutions and preparative chromatography; flammable, evaporates readily.
  • Ethyl acetate and acetone — for workup and crystallization; limited use in aqueous assays.
• Aqueous use: Poor intrinsic water solubility (literature, class). For biological assays, use co-solvent strategies:
  • Prepare concentrated DMSO stock (e.g., 10–50 mM), then dilute into buffer or media ensuring final DMSO ≤0.1–0.5% where compatible.
  • Use solubilizing aids if needed (0.5–1% Tween 80 or Pluronic F-127; or cyclodextrin inclusion complexes); verify that additives do not confound the assay.
• Chromatography considerations:
  • Normal-phase (silica) with hexanes/EtOAc or toluene/EtOAc separates prenylated congeners well.
  • Reversed-phase HPLC: C18 with water–acetonitrile (or MeOH) gradients; add 0.1% formic acid for improved peak shape (analytical practice).
• When to choose alternatives: If strong donor solvents interfere (e.g., with metal-catalyzed steps), use less coordinating solvents (EtOAc, toluene) for workup and purification.

Always filter solutions (0.22 μm PTFE) for analytical injections to remove particulates/undissolved material.

Storage and Reconstitution

Follow the item-specific storage and shipping guidance to preserve integrity.

Item-specific instructions:

• Storage conditions: Protected from light, Store at −80°C (as provided in product data).
• Shipped in: Dry ice packs + Cold packs.
• Appearance: Not specified for this item; refer to CoA/Spec Sheet.

Reconstitution and handling (recommendations for hydrophobic chalcones):

• Solvent: Use anhydrous DMSO to prepare a concentrated stock (e.g., 10–50 mM). Ethanol or methanol may be used where compatible with downstream applications.
• Procedure: Allow vial to equilibrate to room temperature in a desiccated, dark environment before opening to avoid condensation. Weigh rapidly under low light. Add solvent, vortex, and, if necessary, gently sonicate. Filter for analytical work.
• Aliquoting: Divide stock into single-use amber vials or low-bind tubes (e.g., 50–200 μL) to avoid repeated freeze–thaw.
• Storage of solutions: Store aliquots at −80°C (preferred) or −20°C for short term, protected from light and moisture. Avoid >2–3 freeze–thaw cycles.
• Stability: Solutions of phenolic enones may slowly degrade upon prolonged exposure to light/air; prepare fresh working dilutions immediately before use and discard visibly degraded or precipitated solutions.

Always refer to the CoA/Spec Sheet and SDS for lot-specific guidance on stability, compatibility, and safe handling.

Structure and Identity

Licochalcone C is a prenylated chalcone (a flavonoid-type 1,3-diaryl-2-propen-1-one) member of the licochalcone family isolated from Glycyrrhiza (licorice) species. It is commonly used as a reference standard and screening library component in natural product research.

• SKU: L656638
• CAS: 144506-14-9
• PubChem CID: 9840805
• Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• InChIKey: Not specified for this item; refer to CoA/Spec Sheet.

Structural features (general, literature):

• Core scaffold: chalcone (α,β-unsaturated ketone) linking two aromatic rings via a trans-enedione fragment (Ar–CO–CH=CH–Ar').
• Typical substituents in the licochalcone series: phenolic hydroxyls and a prenyl/isoprenyl side chain on one ring (literature, family-level description).
• 2D description: one ring bears phenolic groups and a prenyl substituent; the enone connects to a second phenyl ring variably substituted with phenoxy/methoxy/phenolic groups depending on the specific licochalcone isomer (literature, general).

Notes:

• Exact substitution pattern, stereochemistry about the enone (E preferred, literature) and definitive identifiers should be taken from the item’s CoA/Spec Sheet for this specific lot.

Synthetic Utility

Although most users will employ Licochalcone C as a reference standard or screening compound, its chalcone scaffold provides rich synthetic reactivity for derivatization and SAR studies (general literature guidance):

• Michael acceptor platform: The enone enables conjugate additions with thiols, amines, and carbon nucleophiles (e.g., malonates under base, organocuprates), allowing formation of β-substituted adducts. This is a gateway to elaborated analogs and bioconjugates.
• Cyclization manifolds:
  • Base- or acid-promoted cyclization to flavanones/flavones (e.g., Algar–Flynn–Oyamada oxidation for aurones/flavonols from o-hydroxychalcones).
  • Oxidative cyclizations (I2/DMSO, hypervalent iodine) to heteroannulated products.
• Reduction/oxidation:
  • Selective 1,4-reduction to dihydrochalcones (e.g., catalytic hydrogenation) or 1,2-reduction to allylic alcohols (NaBH4/Luche conditions) as synthetic handles.
• Phenolic diversification: O-alkylation, O-acylation, carbonate/carbamate formation, or late-stage etherifications to tune solubility and electronics.
• Prenyl handle chemistry: Isoprenyl side chains (common in licochalcones) can be oxidized (e.g., to allylic alcohols), cyclized, or cross-coupled after halogenation for scaffold hopping.

Analytical support:

• Reaction monitoring by TLC (UV 254/365 nm) and LC–MS is straightforward due to strong chromophores.
• NMR: vinylic and carbonyl resonances of the enone provide diagnostic signals for tracking transformations and E/Z isomerization.

All conditions should be adapted and optimized for the specific substitution pattern of Licochalcone C.

Target Specificity

No target specificity or validated biological targets are provided for this catalog item.

• Item-specific target/epitope/clone/isotype: Not applicable; this product is a small molecule, not an antibody or protein reagent.
• Literature note: Chalcone enones can act as electrophilic probes toward cysteine-containing proteins in chemoproteomic studies, but specific target engagement for Licochalcone C must be established experimentally in each system.

For any target-related use, design appropriate controls (inactive analogs, scavenger thiols, covalent-inhibitor test panels) and confirm on-target effects with orthogonal assays. Refer to primary literature for system-specific findings and do not generalize across models without validation.

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 144506-14-9, the molecular formula is C21H22O4, and the molecular weight is 338.4 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.