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.
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.
Storage
Protected from light,Store at -80°C
Verschickt in
Dry ice packs + Cold packs
Dieses Produkt erfordert Kühlkettenversand. Grundversand und andere Economy-Optionen sind nicht verfügbar.
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.
Zertifikate (CoA, COO, BSE/TSE und Analyse-Diagramm)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Chemische und physikalische Eigenschaften
Löslichkeit
DMSO : 33.33 mg/mL (98.49 mM; Need ultrasonic)
Flammpunkt (°F)
Not applicable
Flammpunkt (°C)
Not applicable
Molekulargewicht
338.400 g/mol
XLogP3
4.900
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
6
Exact Mass
338.152 Da
Monoisotopic Mass
338.152 Da
Topological Polar Surface Area
66.800 Ų
Heavy Atom Count
25
Formal Charge
0
Complexity
484.000
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
Lösungsrechner
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Application Protocols
No item-specific tested application protocols are provided. As general guidance for research use of hydrophobic small molecules:
Preparing stock solutions
Dissolve in anhydrous DMSO at a defined concentration (e.g., 10–50 mM), vortex and sonicate if needed. Filter (0.22 µm PTFE) for sterile applications.
Aliquot and store frozen to avoid repeated freeze–thaw.
Adding to aqueous assays
Pre‑dilute the DMSO stock into warm medium/buffer to a small intermediate volume, then add to the bulk with rapid mixing. Maintain consistent vehicle % across controls and treatments (commonly ≤0.1–1% v/v DMSO).
Analytical reference standard use
Dry under gentle nitrogen to constant weight before preparing calibration solutions.
Use amber vials; record exact solvent composition and temperature for reproducible response factors.
These are general best practices. For validated, application‑specific protocols, consult peer‑reviewed literature or develop internal SOPs.
Biological Roles
Background (literature/general): Licochalcone C is a prenylated chalcone isolated from Glycyrrhiza (licorice) species. Chalcones are open‑chain flavonoids biosynthetically derived from the condensation of p‑coumaroyl‑CoA with malonyl‑CoA via chalcone synthase, followed by tailoring steps (e.g., O‑methylation, prenylation).
Putative roles in plants (literature)
Chemical defense: Prenylated flavonoids often function as phytoalexins, contributing to antimicrobial and anti‑herbivory defenses.
Signaling and pigmentation: Conjugated systems contribute to UV protection and pigmentation; phenolic groups aid in ROS scavenging in planta.
Biochemical behavior (general for prenylated chalcones)
Michael acceptor reactivity toward thiols can modulate redox‑sensitive proteins in vitro; phenolic moieties participate in H‑bonding and metal chelation.
Enhanced membrane affinity due to prenylation may influence cellular uptake in cell‑based research models (assay‑dependent; verify empirically).
Research utility
Serves as a chemical standard in metabolomics/food chemistry to track licorice‑derived constituents.
Employed in structure–activity studies comparing chalcone, flavanone, and aurone scaffolds.
Important: All biological remarks are literature‑based and provided to contextualize research use only. No medical, therapeutic, or diagnostic claims are made or implied.
Buffer Applications
Not typically applicable. Licochalcone C is a neutral, hydrophobic small molecule and does not function as a buffering agent.
Practical note
If adding to buffered systems for assays, dissolve first in a compatible organic cosolvent (e.g., DMSO or ethanol), then titrate into the buffer under vigorous mixing to avoid precipitation.
Maintain final organic content within assay‑tolerated limits (commonly ≤0.1–1% v/v), and include vehicle controls.
Green Alternatives
Greener handling of Licochalcone C focuses on solvent choice and process conditions, since the molecule itself is fixed.
Greener dissolution and processing (general guidance)
Prefer bio‑derived solvents where feasible: 2‑MeTHF (vs THF), ethyl acetate (vs DCM), ethanol (vs isopropanol/MeOH depending on context).
For chromatographic purification, consider EtOAc/hexane or heptane/IPA systems over chlorinated eluents; for LC, water/ethanol or water/ACN with minimal volatile modifiers.
Example comparison (literature/general)
| Use case | Conventional | Greener alternative | Trade‑offs |
|---|---|---|---|
| Stock solutions | DMSO | Glycerol carbonate, Cyrene (where compatible) | Solubility often lower; assay compatibility must be verified |
| Workup/extraction | DCM/CHCl3 | EtOAc/MTBE | Partitioning and selectivity differ; may need additional washes |
| Hydrogenation solvent | EtOH/AcOEt | EtOH (bio‑sourced) or water/EtOH with surfactant | Mass transfer and selectivity can change |
| Reduction of waste | Large‑volume silica | Recyclable silica, flash systems with greener eluents | May require method reoptimization |
Process intensification
Use catalytic rather than stoichiometric reagents for modifications (e.g., catalytic hydrogenation over Pd/C at ambient pressure where possible).
Employ light protection to reduce degradation and rework, improving overall E‑factor.
Assess greenness with tools like CHEM21 or PMI Calculator; verify compound stability and assay compatibility when changing solvents.
Pharmaceutical Uses
No excipient or pharmacopeial status is specified for this item; it is supplied strictly for research use only.
Research and manufacturing context (general/literature):
Analytical reference standard
Used to develop and validate QC methods (HPLC/UPLC‑MS) for licorice‑derived raw materials, extracts, and finished botanical ingredients. Supports identity, assay, and stability testing.
Impurity/marker profiling
Aids in establishing marker panels and fingerprinting libraries for botanical authentication and stability studies.
Preformulation research (non-clinical)
Solubility, polymorphism, and solid‑state stability assessments in early discovery or natural product chemistry groups; informs formulation strategies for in vitro work.
No therapeutic, prophylactic, or diagnostic applications are claimed or supported for this product. Consult internal QA procedures and applicable regulations when using as an analytical reference material.
Physical Properties
Item-specific properties are not provided in the Product Data; consult the CoA/SDS for definitive specifications.
Appearance (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
Molecular weight (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
Molecular formula (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
General/literature characteristics for prenylated chalcones (for methodological planning; not product specifications):
State: typically a yellow to orange crystalline solid due to extended π‑conjugation (literature, chalcone class).
Poor/insoluble: water and aqueous buffers without cosolvent.
Lipophilicity: elevated relative to non‑prenylated chalcones (literature); expect higher logP due to isoprenyl group.
UV–Vis: strong absorption in the near‑UV; π→π* band for the chalcone system often 330–380 nm (literature; exact λmax depends on substitution and solvent).
Acid/base behavior: phenolic OH (weakly acidic), enone is neutral; no formal pKa for the enone, phenols typically pKa ~9–10 depending on substitution (literature, general ranges).
Always verify critical method parameters (e.g., extinction coefficients, λmax, solubility limits) empirically for your solvent system. These literature notes are provided for planning only.
Quality and Grades
Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
Interpretation and guidance (general for small-molecule reference standards and screening compounds):
Research grade vs. analytical reference standard
When used as a reference marker (e.g., for phytochemical QC), an analytical/reference standard grade emphasizes high chemical purity and well‑documented identity (NMR, HPLC/UPLC purity, MS). If your application is quantitative (e.g., calibration curves), request a full CoA with assay method and uncertainty.
Chromatography suitability
For LC/UPLC method development, low non-volatile residue and high chemical purity minimize ghost peaks and baseline drift. Where UV detection is used, knowledge of λmax and secondary bands assists in setting detection wavelengths.
Stabilizer content
No stabilizers are indicated in the Product Data. If stabilizers/antioxidants are added by the manufacturer, these will be stated on the CoA. Absence of such a statement should not be interpreted as confirmation of “stabilizer‑free”; verify if critical to your method.
Batch-to-batch documentation
Expect provision of spectral identity (1H/13C NMR), chromatographic purity, and water content (e.g., Karl Fischer) on request. If specific impurity limits (e.g., isomeric chalcones, flavanones) matter for your work, define acceptance criteria prior to purchase.
Conclusion: Consult the lot-specific CoA to confirm purity grade, analytical data set, and any additives for this SKU.
Reaction and Applications
As a reactive α,β‑unsaturated ketone bearing phenolic groups, Licochalcone C is a versatile target and derivatization substrate in synthetic and medicinal chemistry workflows.
Typical research uses (non-clinical)
Reference standard for licorice (Glycyrrhiza) metabolite profiling (HPLC/UPLC‑MS method development, quantitation, spiking recovery studies).
Chemical probe in redox/thiol chemistry due to the enone’s Michael‑acceptor reactivity (literature observations across chalcones).
Transformations on the chalcone scaffold (literature/general)
Conjugate additions (Michael reactions): soft nucleophiles (thiols, amines, malonates) add across the enone under base or Lewis acid catalysis.
Hydrogenation: selective C=C reduction (Pd/C, H2) to dihydrochalcones; full hydrogenation reduces the carbonyl under harsher conditions.
Cyclizations to flavanones/aurones: base- or acid‑promoted intramolecular oxa‑Michael cyclization; Algar–Flynn–Oyamada oxidation to flavonols from o‑hydroxychalcones.
O‑functionalization: phenolic O‑alkylation/acylation to adjust lipophilicity and block tautomerization.
Analytical applications
Stability studies (light/oxygen) to define storage and assay conditions.
Spectroscopic fingerprinting (UV–Vis, NMR, HRMS) for method validation.
Practical tips
Minimize base exposure unless intended; phenolate formation accelerates side reactions.
Control isomerization: strong light or base can induce E/Z isomerization; work under subdued light (item requires protection from light).
For bioassays, prepare fresh DMSO stocks or aliquot and freeze to avoid repeated thawing that may promote oxidation.
All applications above are for laboratory research and analytical development only.
Reaction Conditions
General literature guidance for chalcone transformations (not product specifications; optimize for your system):
Conjugate (Michael) additions
Conditions: base catalysis (e.g., K2CO3, DBU) in polar aprotic solvents (DMF, DMSO, MeCN) at rt–60 °C; or Lewis acids (e.g., BF3·Et2O) for softer activation.
Catalyst: Pd/C (5–10 wt%), H2 (1 atm) in EtOH/EtOAc at rt–40 °C.
Tips: Protect phenols to avoid over‑reduction or catalyst poisoning; stop once C=C is consumed to preserve carbonyl.
Cyclization to flavanones/aurones
Base-promoted oxa‑Michael: K2CO3 or t‑BuOK in MeOH/THF, 0–25 °C to control E/Z isomerization.
Oxidative cyclization (AFO to flavonols, when ortho‑OH present): alkaline H2O2 or t‑BuOOH with phase-transfer catalysis; maintain low temperatures to suppress over‑oxidation.
O‑alkylation/acylation of phenols
Conditions: alkyl halide or acyl chloride with K2CO3/NaH in acetone/DMF; 0–25 °C. Protect enone if undesired conjugate addition is an issue.
Analytical and handling conditions
Work under subdued light (item requires light protection). Use anhydrous solvents for base‑sensitive steps.
Purification: normal‑phase silica with hexane/EtOAc gradients; for strongly retained phenolics, add a small % of Et3N to suppress tailing or switch to reverse phase.
Reported yields vary widely (40–90%) depending on substitution and conditions; conduct small‑scale scouting before scale‑up.
Safety and Handling
Regulatory note: For research use only. Not for human or veterinary use.
GHS/SDS information (item-specific)
Signal word: Not specified for this item; refer to SDS.
Hazard statements (H‑statements): Not specified for this item; refer to SDS.
GHS classification and pictograms: Not specified for this item; refer to SDS.
General hazards and precautions (chalcone/polyphenol class; literature/good practice)
May cause irritation to eyes, skin, and respiratory tract upon contact or inhalation of dust.
Handle under a chemical fume hood; avoid dust generation and aerosolization.
Protect from light (item-specific) to minimize photoisomerization or oxidative degradation.
PPE
Lab coat, nitrile gloves, safety glasses or splash goggles.
Use a dust mask or respirator if powder handling generates particulates (per risk assessment and SDS).
Incompatibilities and stability
Avoid strong oxidizers and strong bases/acids that can promote decomposition or undesired reactions (e.g., Michael additions, polymerization).
Moisture and air exposure can accelerate oxidative changes in phenolics; keep containers tightly closed, minimize headspace, and purge with inert gas if long-term storage is anticipated.
First-aid overview (consult SDS for details)
Skin/eye contact: Rinse with copious water for ≥15 min; remove contaminated clothing; seek medical attention if irritation persists.
Inhalation: Move to fresh air; monitor breathing; seek medical attention as needed.
Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
Waste disposal
Collect as organic hazardous waste following institutional and local regulations.
Solvent Selection
Licochalcone C is a lipophilic, prenylated chalcone with phenolic groups—insoluble in water but readily solubilized by polar aprotic and certain protic organic solvents.
Stock solutions: DMSO (10–50 mM typical), DMF, or ethanol. Warm gently (≤40 °C) and vortex/sonicate to aid dissolution. Avoid strong base unless reaction-specific.
Working dilutions into aqueous media require cosolvent and/or surfactant (e.g., ≤1% DMSO v/v, or 0.5–2% ethanol with 0.01–0.1% nonionic surfactant). Pre‑mix organic solvent with compound before adding buffer to prevent precipitation.
Polarity and miscibility (general)
Polarity class: moderately nonpolar aromatic with a conjugated enone; behaves as a neutral, H‑bond donor/acceptor.
Miscibility: insoluble in water; soluble in DMSO/DMF; moderately soluble in lower alcohols and esters; variable in chlorinated solvents.
When to choose each solvent
DMSO: best for maximal solubility and stable cryo‑stocks; widely compatible with screening assays at low percentages.
Ethanol/methanol: suitable for spectroscopic studies and certain bioassays where alcohol tolerance is higher.
Acetonitrile/ethyl acetate: useful for preparative handling and chromatography; tune elution with hexane/IPA or MeOH/water (with acid modifier) systems.
Small comparison (general guidance)
DMSO vs ethanol: DMSO usually affords higher solubility and better freeze–thaw stability; ethanol offers lower matrix effects in LC‑MS but may limit maximum concentration.
ACN vs MeOH (LC): ACN often yields sharper peaks and lower backpressure; MeOH can improve selectivity for phenolics.
Always verify solubility and stability empirically in your chosen solvent system.
Storage and Reconstitution
Item-specific storage and shipping
Storage conditions: Protected from light, Store at -80 °C (per Product Data).
Light sensitivity: Use amber containers or foil wrap. Minimize exposure during weighing and solution prep.
Atmosphere: Keep tightly closed; consider inert gas backfill after opening to limit oxidative degradation of phenolic/enone systems.
Reconstitution and stock preparation (general)
Solvents: DMSO is preferred for high‑concentration stocks; ethanol or DMF are alternatives. Water is not recommended due to poor solubility.
Procedure: Allow vial to equilibrate to room temperature in the dark before opening to prevent moisture condensation. Weigh quickly, dissolve in dry solvent with mild warming (≤40 °C) and vortex/sonicate. For analytical use, consider 0.22 µm PTFE filtration.
Aliquoting: Dispense into amber, low‑headspace vials or microtubes; store at −80 °C. Avoid repeated freeze–thaw; thaw only what is needed.
Stability notes
No lot‑specific stability data are provided. Monitor for discoloration or precipitation and verify integrity by LC or NMR after prolonged storage.
For definitive stability limits, retest periods, and solution shelf life, refer to the lot‑specific CoA/SDS.
Structure and Identity
Licochalcone C is a prenylated chalcone (open‑chain flavonoid) occurring in Glycyrrhiza spp. It features an α,β‑unsaturated ketone linking two substituted phenyl rings, with phenolic hydroxyls and an isoprenyl (3‑methyl‑2‑butenyl) substituent typical of licochalcones.
Item-specific identifiers (from Product Data)
Product name: Licochalcone C (SKU: L651345)
CAS: 144506-14-9
PubChem CID: 9840805
InChIKey: 393756 (as provided; note: standard InChIKeys are typically 27 characters—consult CoA/SDS for confirmation)
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.
Structural features (general/literature description of chalcones)
Conjugated enone (α,β‑unsaturated carbonyl) acting as a soft Michael acceptor.
Two aryl rings (A- and B-rings) connected by the enone linker; phenolic –OH groups capable of H‑bonding and metal chelation.
Prenyl/isoprenyl substituent increasing lipophilicity and membrane permeability.
Typically exists as the E‑(trans) isomer across the Cα=Cβ double bond (literature/common for chalcones).
2D structure (verbal)
Ring A bearing phenolic OH and a prenyl chain; an enone chain (–CO–CH=CH–) extends to ring B, which carries additional phenolic OH. The extended conjugation imparts strong UV absorbance in the near‑UV/visible region (literature).
Synthetic Utility
Licochalcone C is a synthetically tractable chalcone bearing phenolic OH groups and a prenyl substituent. While often used as a reference standard/target, it also serves as a platform for SAR and derivatization.
Functional group reactivity (literature/general)
Enone: undergoes Michael additions (soft nucleophiles), 1,2‑additions with hard nucleophiles, selective hydrogenation, and photocyclization under specific conditions.
Phenols: O‑alkylation, O‑acylation, etherification, and protective group chemistry (e.g., MOM, Bn) to tune reactivity and solubility.
Prenyl: susceptible to oxidation, hydroboration–oxidation, epoxidation, or electrophilic additions enabling diversification of side chains.
Scaffold remodeling
Intramolecular oxa‑Michael cyclization to flavanones/aurones; oxidative cyclizations (Algar–Flynn–Oyamada) to flavonols when ortho‑hydroxylation is present.
Reduction to dihydrochalcones or further to diarylpropanones.
Retrosynthetic perspective
Accessed via Claisen–Schmidt condensation between appropriately substituted acetophenone and benzaldehyde fragments, followed by prenylation (e.g., O‑ to C‑prenyl rearrangements or direct C‑prenylation strategies). Protecting‑group tactics help control regioselectivity.
Utility in method development
Benchmark substrate to evaluate chemoselectivity in conjugate addition vs. cyclization; probe for base/Lewis acid catalysis outcomes.
These points are literature‑based, serving as planning guidance for derivatization and scaffold exploration.
Target Specificity
Not applicable to this product type. Licochalcone C is a small molecule, not a biologic or antibody. No antigen, epitope, clone, isotype, or species reactivity information applies.
Häufig gestellte Fragen
What is the purity of this product?
This product is supplied at ≥99% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.
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. InChIKey WBDNTJSRHDSPSR-KPKJPENVSA-N.
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.
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