Licoagrochalcone C , CAS No.325144-68-1

CAS: 325144-68-1 Cat. No.: L1447265 Formula: C₂₁H₂₂O₅ Molecular Weight: 354.40

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Licoagrochalcone C, a flavonoid, reveals efficacious inhibitory activity on NF-κB transcription. Licoagrochalcone C shows significant inhibitory activity on LPS -induced NO production.

Specifications

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Action Type

INHIBITOR

Names and Identifiers

Molecular Weight

354.40

Application Protocols

No tested biological or analytical application protocols are provided for this SKU. General guidance for small-molecule reference standards (literature-based, not product-specific):

• Stock preparation:
  • Dissolve the solid in anhydrous DMSO to prepare a concentrated stock (e.g., 10–50 mM). Filter through a PTFE membrane (0.2 µm) if particulate is present.
• LC–UV/LC–MS calibration:
  • Prepare serial dilutions in acetonitrile:water or methanol:water with 0.1% formic acid (for positive mode) or 5–10 mM ammonium acetate (for negative mode). Use amber vials to minimize photodegradation.
• Recovery checks:
  • Verify adsorption losses at low concentrations by bracketing with solvent blanks and pre-rinsing vials.
• Biochemical assays:
  • Add DMSO stock to buffer under vigorous mixing; keep final DMSO ≤0.5–1% v/v unless your assay validates higher. Include vehicle controls.

For validated, item-specific methods (e.g., HPLC conditions, extinction coefficients), consult the Aladdin CoA/Spec Sheet or develop in-house SOPs.

Biological Roles

No item-specific biological data are provided for this SKU. The following summarizes literature context for chalcones and licorice-derived phenylpropanoids in biochemistry, without making clinical claims:

• Origin and metabolism (plants): Chalcones are biosynthetic intermediates in the flavonoid pathway, formed by chalcone synthase (a type III polyketide synthase) from p-coumaroyl-CoA and malonyl-CoA. Prenylation by prenyltransferases yields more lipophilic derivatives often found in Glycyrrhiza species (licorice).
• Molecular interactions (in vitro, literature): The α,β-unsaturated carbonyl can act as a soft electrophile toward thiol-containing biomolecules in model systems, enabling reversible or irreversible adduct formation depending on conditions. Phenolic groups can engage in hydrogen bonding and metal chelation in biochemical assays.
• Physicochemical features: Prenylated chalcones show increased membrane association and altered partitioning versus nonprenylated analogs, influencing apparent activity and assay readouts in cell-free systems (literature).
• Analytical biomarkers: Such compounds are frequently targeted in metabolomics and botanical authentication workflows as marker constituents of licorice extracts. They serve as reference points for profiling, stability testing, and standardization.
• Stability in assay media: Chalcones may undergo Michael additions with nucleophiles (e.g., glutathione) or isomerization under basic pH; care should be taken to control vehicle composition and pH during biochemical experiments to ensure interpretability.

All uses of this product are for research only. For lot-specific attributes or tested bioassays, consult the CoA and literature relevant to licoagrochalcones.

Buffer Applications

This product is a hydrophobic small-molecule standard rather than a buffering reagent. It is not used to prepare pH buffer systems.

Practical notes (general):

• If dosing into aqueous buffers for assays, prepare concentrated DMSO stocks and add to the buffer with vigorous mixing to reach the desired final concentration while keeping the cosolvent fraction low (commonly ≤0.5–1% v/v; literature practice).
• Control pH carefully: chalcone enones can isomerize or react under strongly basic conditions; maintain near-neutral pH unless a specific reaction is intended.

For recipes and pH ranges of common biological buffers (PBS, HEPES, Tris), refer to standard references; this product does not serve as a buffer component.

Green Alternatives

When handling chalcone-type small molecules, solvent choice dominates the sustainability profile. While item-specific formulation is not provided, you can improve the greenness of extractions, reactions, and purifications (literature-based guidance):

• Greener solvent swaps (comparison, general):

  • Replace dichloromethane with ethyl acetate or 2-MeTHF for extractions when partitioning allows.
  • Prefer ethanol or isopropanol over methanol when feasible (lower toxicity; similar polarity).
  • Use 2-MeTHF or CPME as alternatives to THF in base-catalyzed condensations or reductions, noting different peroxide tendencies and water miscibility.

• Example tradeoffs (literature):

  • 2-MeTHF: renewable source, good performance in many condensations; slightly higher boiling point can aid recrystallizations but complicates solvent removal.
  • CPME: hydrophobic ether suitable for biphasic catalysis; lower tendency to form peroxides than THF; however, odor and supply chain considerations apply.
  • Ethyl acetate: biodegradable, low toxicity; may have limited solubility for highly hydrophobic chalcones compared to acetonitrile or DMSO.

• Purification:

  • Favor reverse-phase water–acetonitrile gradients over chlorinated normal-phase systems when compatible with analyte stability.
  • Recycle solvent where possible; employ short-gradient UHPLC for analytical work to minimize mobile-phase volume.

• Energy and waste:

  • Conduct reactions at ambient temperature and higher concentrations when selectivity permits.
  • Choose catalytic over stoichiometric conditions for derivatizations (e.g., catalytic base or organocatalysts for cyclizations).

Balance green swaps against analytical requirements and recovery; validate performance before scale-up.

Pharmaceutical Uses

No pharmacopeial or excipient role is specified for this item; it is offered for research use only.

Relevant research/manufacturing contexts (general, non-clinical):

• Reference standard: Prenylated chalcones are used as analytical standards for quality control and authentication of botanical raw materials and extracts (e.g., licorice). They assist in method validation (specificity, linearity, accuracy) for HPLC/LC–MS assays.
• Process development studies: Employed in extraction and purification method development to optimize solvent systems, adsorption/desorption on resins, and crystallization parameters for polyphenolic constituents.
• Stability studies: Used to establish degradation pathways under ICH-like stress conditions (light, heat, oxidative, and pH) for natural-product-containing matrices. Findings guide packaging and storage but do not imply therapeutic application.

No therapeutic, diagnostic, or clinical claims are made or should be inferred. For regulatory-grade standards or compendial specifications, consult appropriate pharmacopeial sources and Aladdin’s CoA/Spec Sheet.

Physical Properties

Item-specific physicochemical parameters are not provided in the product data.

• Item-specific values (this product):

  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.
  • Melting point: Not specified for this item; refer to CoA/Spec Sheet.
  • Boiling point: Not specified for this item; refer to CoA/Spec Sheet.
  • Density: Not specified for this item; refer to CoA/Spec Sheet.
  • Solubility (quantitative): Not specified for this item; refer to CoA/Spec Sheet.
  • LogP, pKa, refractive index, UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.

• General literature expectations for prenylated chalcones (not item-specific specs):

  • Physical state: typically crystalline solids or amorphous powders with yellow to orange coloration due to the conjugated enone chromophore.
  • Solubility profile: sparingly soluble in water; readily soluble in polar aprotic and protic organic solvents such as DMSO, DMF, methanol, ethanol, acetone, and acetonitrile. Stock solutions for bioassays are commonly prepared in anhydrous DMSO.
  • UV–Vis: conjugated enones show strong π→π* absorbance in the near-UV (approx. 330–380 nm region; literature) with solvent- and substitution-dependent maxima.
  • Stability: chalcone enones are generally stable as dry solids under inert, cool storage; prolonged exposure to strong base, light, or heat may induce isomerization or Michael additions (literature).

Always confirm exact specifications, including purity and solubility limits for your lot, from the Aladdin CoA/Spec Sheet and SDS before use.

Quality and Grades

• Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.

Guidance on interpreting grade and documentation (general):

• Natural product standards like chalcones are commonly offered as “research grade” or “analytical standard” quality. Research grade prioritizes chemical identity and typical assay purity for discovery work; analytical standard emphasizes traceable purity with detailed impurity profiling suited to quantitative methods (HPLC/LC–MS calibration). Abbreviations such as “≥98% (HPLC)” indicate assay purity by a specified chromatographic method under stated conditions.
• If stabilizers are used (e.g., antioxidant or inert carrier), they will be declared on the CoA. Presence of stabilizers can influence UV baselines or MS ionization; verify compatibility with your analytical method. For this SKU, stabilizer information is Not specified for this item; refer to CoA/Spec Sheet.
• Batch-to-batch documentation: Each lot should include identity confirmation (e.g., 1H/13C NMR, HRMS), chromatographic purity, and water content if relevant. When developing quantitative methods, match the lot’s purity-corrected concentration to your calibration strategy.
• Practical tip: For hydrophobic analytes, adsorption losses can affect low-µg/mL solutions. Pre-rinse glassware with the working solution or add a small percentage of organic modifier (e.g., 0.1–1% DMSO) in aqueous mobile phases to improve recovery (method-development literature guidance).

Consult the Aladdin CoA/Spec Sheet for the definitive grade, purity, and analytical data for SKU L1447265.

Reaction and Applications

Licoagrochalcone C, as a prenylated chalcone, is useful as a reference standard and as a functional scaffold in organic synthesis and method development. The following are literature-based applications for chalcone-type compounds (not product-specific claims):

• Reference and analytical standard:

  • Calibration of HPLC/UPLC–UV or LC–MS methods for licorice-derived metabolite profiling and natural products QC.
  • System suitability testing for reverse-phase separations of polyphenolic enones (monitor retention, peak shape, and stability).

• Chemical reactivity studies (enone chemistry):

  • Acts as a Michael acceptor in conjugate additions (e.g., thiol or amine addition) enabling formation of β-substituted ketones; useful for mechanistic studies of soft nucleophile additions.
  • Undergoes cyclizations to flavanones or aurones via base- or acid-catalyzed transformations, showcasing chalcone–flavanone interconversion (literature).

• Derivatization for SAR libraries:

  • O-alkylation/acylation of phenolic OH groups to tune lipophilicity and stability.
  • Prenyl group modifications (oxidation, epoxidation, or cross-coupling if suitably functionalized) to vary sterics/electronics.
  • Halogenation or nitration at activated ring positions for downstream cross-coupling studies.

• Photophysical/analytical uses:

  • Conjugated enone chromophore provides robust UV response, aiding trace-level detection in complex extracts.

Practical tips (general):

• Protect from strong base during storage; for planned reactions, freshly prepare solutions and minimize exposure to nucleophiles unless desired.
• Use dry, oxygen- and light-limited conditions when evaluating kinetics of Michael additions to prevent side reactions.
• For LC–MS, add 0.1% formic acid (positive mode) or 5–10 mM ammonium acetate (negative mode) to improve ionization and peak shape (method-development literature).

Reaction Conditions

No item-specific reaction constraints are provided. The following general conditions are reported in the literature for chalcone chemistry and may be adapted to prenylated analogs; optimize for your substrate and consult primary sources:

• Conjugate additions (Michael):

  • Solvents: ethanol, methanol, acetonitrile, THF, or DMSO depending on nucleophile.
  • Bases/catalysts: secondary amines, DBU, or organocatalysts; for thiol additions, base (e.g., Et3N, K2CO3) at 0.1–1.0 eq.
  • Temperature/time: 0–25°C, 0.5–24 h; monitor by TLC/HPLC.

• Cyclization to flavanones:

  • Conditions: intramolecular o-hydroxy-assisted cyclization using K2CO3 or NaOH in ethanol or aqueous alcohol; or Lewis acids (AlCl3, BF3·Et2O) in DCM/MeCN.
  • Temperature: 0–60°C; times from 30 min to several hours.

• O-alkylation/acylation (phenols):

  • Bases: K2CO3, Cs2CO3 in acetone/ACN/DMF; alkyl halide or acyl chloride (1.1–1.5 eq).
  • Temperatures: ambient to 60°C; 1–12 h.

• Prenyl oxidations/epoxidations:

  • Reagents: mCPBA or DMDO for epoxidation (DCM/MeCN, 0–25°C); hydroboration–oxidation for alcohol formation (THF, 0–25°C).

• Hydrogenation of enone:

  • Catalysts: Pd/C or Raney Ni under H2 (1–3 bar) in EtOH/EtOAc; 20–25°C; 1–6 h to reduce C=C selectively; stronger conditions reduce the carbonyl.

• Analytical monitoring:

  • UV detection around the chalcone band facilitates LC tracking; add volatile modifiers (0.1% formic or acetic acid) for improved peak shape.

All conditions are literature guidance. Substitution patterns (e.g., prenyl, phenols) can significantly influence rates/selectivity—perform small-scale trials and confirm by NMR/LC–MS.

Safety and Handling

• GHS classification, signal word, pictograms, and H-statements: Not specified for this item; refer to SDS.
• Research use: For research use only (not for human or veterinary use).

General safety guidance for chalcone-type small molecules (literature-based; not product-specific):

• Hazards and exposure: Many chalcones are lipophilic organics that can cause skin/eye irritation and may be harmful if swallowed or inhaled. Avoid dust formation and aerosolization. Use local exhaust ventilation in weighing and dissolution steps.
• PPE: Wear lab coat, safety glasses, and appropriate chemically resistant gloves (e.g., nitrile). Use in a chemical fume hood. Avoid skin contact; wash thoroughly after handling.
• Storage incompatibilities: Avoid strong bases (risk of enone conjugate addition), strong nucleophiles, and strong oxidants. Protect from light and moisture to minimize degradation or isomerization of the α,β-unsaturated carbonyl.
• Thermal/light sensitivity: Conjugated enones may undergo photochemical reactions; store protected from light as good practice.
• First aid (overview; defer to SDS):
  • Inhalation: move to fresh air; seek medical attention if symptoms persist.
  • Skin contact: wash with soap and water; remove contaminated clothing.
  • Eye contact: rinse cautiously with water for several minutes; remove contact lenses if present and easy to do; continue rinsing.
  • Ingestion: rinse mouth; seek medical advice; do not induce vomiting unless directed by medical personnel.

Always consult the Aladdin SDS for authoritative hazard classification and emergency measures.

Solvent Selection

This product is a hydrophobic small molecule (prenylated chalcone class; literature), typically handled as a dry solid and dissolved in organic solvents for stock solutions and reactions.

• Polarity/miscibility (literature, class guidance):

  • Water: poor solubility expected.
  • Polar aprotic: DMSO and DMF typically provide high solubility for chalcones; acetonitrile and acetone give moderate to good solubility.
  • Polar protic: methanol and ethanol often dissolve chalcones well; isopropanol moderately.
  • Nonpolar/medium polarity: ethyl acetate, dichloromethane, and toluene can be useful for extraction and chromatography; solubility varies with substitution.

• Selection by application:

  • Bioassay stocks: prepare concentrated anhydrous DMSO stocks (e.g., 10–50 mM; literature practice), dilute into assay buffer with final DMSO ≤0.5–1% v/v to minimize vehicle effects.
  • Synthetic use: for aldol-derived chalcone transformations, use ethanol, methanol, or THF/EtOH mixtures; for metal-catalyzed steps or photochemistry, acetonitrile or DMF may be preferred (literature).
  • Purification: normal-phase silica gel with hexanes/ethyl acetate gradients or reverse-phase C18 with water–acetonitrile (0.1% acid) are common.

• Comparison (general):

  • DMSO vs MeOH: DMSO affords highest solubility and best stability in freezer stocks; methanol is convenient but more volatile and can participate in reactions under basic conditions.
  • ACN vs DMF: ACN is lower boiling and easier to remove; DMF dissolves more polar impurities but is harder to evaporate.

Always verify solvent compatibility with your target application and reference the CoA for any item-specific limitations.

Storage and Reconstitution

• Storage conditions (item-specific): Store at -20°C. Protect from light and moisture. Shipped in ice chest with ice pads to maintain a low-temperature chain.
• Container handling: Keep tightly closed in the original amber container. Allow the vial to equilibrate to room temperature before opening to prevent condensation.

Reconstitution (general guidance for chalcone-type standards; not item-specific specs):

• Solvent: Prepare concentrated stocks in anhydrous DMSO or DMF to maximize solubility and stability. Ethanol or methanol may be used if compatible with downstream applications.
• Typical stock concentrations: 10–50 mM are commonly used in research settings. Adjust based on your solubility testing.
• Filtration: If needed, filter reconstituted solutions through 0.2 µm PTFE to remove particulates.

Stability and aliquoting (general):

• Aliquot stocks to minimize freeze–thaw cycles. Store aliquots at -20°C (or lower) in amber vials. Avoid repeated light exposure.
• Working solutions in aqueous media are best prepared fresh; prolonged exposure to basic pH or nucleophiles can lead to reaction at the enone. Monitor by HPLC if solutions must be stored.

Disposal: Follow institutional and local regulations for organic chemical waste.

Note: For definitive stability, purity, and compatibility information for SKU L1447265, refer to the Aladdin CoA/Spec Sheet and SDS. Research use only.

Structure and Identity

Licoagrochalcone C is a member of the licorice-derived prenylated chalcone family (phenyl–propenone scaffold), used as a small-molecule research standard in natural products and medicinal chemistry workflows.

• Item-specific identifiers (this product):

  • CAS: 325144-68-1
  • Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
  • InChIKey: 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 licoagrochalcones/chalcones; not item-specific specs):

  • Core motif: an α,β-unsaturated carbonyl (chalcone) linking two aromatic rings (A–ring and B–ring) in a trans-enone arrangement.
  • Typical substitution: phenolic hydroxyl groups on one or both rings, and one or more lipophilic substituents (e.g., prenyl/isoprenyl) that increase hydrophobicity and membrane affinity in model systems.
  • Conjugation: extended π-system across Ar–CO–CH=CH–Ar supports characteristic UV–Vis absorbance in the near-UV (literature, chalcones in general).
  • Stereochemistry: chalcones generally exist as E-enones about the C=C bond (literature). No stereocenters are present in the parent chalcone scaffold; any chirality would arise only from chiral substituents (if present).

• 2D structure in words (literature, class description): two substituted phenyl rings connected by an enone linker (Ar1–CO–CH=CH–Ar2); one ring commonly bears phenolic OH groups, while a prenyl group may be attached to increase lipophilicity.

Note: For exact atom connectivity, canonical SMILES, and analytically verified identity for this SKU, consult the CoA/Spec Sheet.

Synthetic Utility

As a prenylated chalcone, Licoagrochalcone C provides a versatile electrophilic scaffold for derivatization and methodology studies (literature-based; not product-specific specifications):

• Functional group reactivity:

  • α,β-Unsaturated ketone (enone): undergoes 1,4-conjugate additions with soft nucleophiles (thiols, enolates, amines), allowing rapid access to β-substituted ketones.
  • Phenolic hydroxyls (if present): amenable to O-alkylation/acylation, carbonate/urethane formation, and Mitsunobu-type inversions when translated to appropriate substrates.
  • Prenyl substituent: can be oxidized (epoxidation, hydroxy-functionalization), isomerized, or used as a handle for further C–C bond formation after selective activation.

• Scaffold editing and ring closures:

  • Cyclization to flavanones or aurones under base or Lewis/Brønsted acid catalysis demonstrates chalcone–flavonoid interconversion.
  • Heteroannulation with o-hydroxychalcones yields benzofuran or xanthone-type frameworks.

• Late-stage diversification:

  • Electrophilic aromatic substitution (halogenation, nitration) on activated rings for subsequent cross-coupling (Suzuki, Sonogashira) after installing suitable leaving groups.
  • Triazole conjugation via azide–alkyne cycloaddition if an alkyne-bearing linker is appended to the phenolic positions.

• Method-development uses:

  • Test substrate for catalysis (organocatalytic Michael additions, enantioselective hydrogenations of enones, photoredox-mediated conjugate additions), thanks to its robust UV detectability.

This scaffold supports both discovery of reactivity and creation of small SAR panels by systematic modification of the enone, phenols, and prenyl moieties.

Target Specificity

This product is a small-molecule chalcone standard, not an antibody or affinity reagent. No antigen/epitope, clone, isotype, or species reactivity applies.

• Item-specific target data: Not applicable.
• For biochemical screening, any target engagement must be determined empirically under your assay conditions. No target specificity is provided for this item.