≥98% for sensitive chromatographic and analytical workflows requiring minimal baseline interference.
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Storage & shipping
Protected from light,Store at -80°C Ships Dry ice packs + Cold packs Check lot-specific COA for exact specifications.
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Quality documents
SDS, COA, datasheet, and spec sheet available for download. Lot-specific COA accessible via lot number lookup.
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Literature proof
Cited in 1 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.
Panoramica
Ilexgenin A is a pentacyclic triterpenoid, which extracted from Ilex hainanensis Merr. Ilexgenin A can be used for the research of inflammation and cancer.
In Vitro
Ilexgenin A (0~100 μM; 24 hours; HT 29 and HCT 116 cells) effectively decreases cell viability in HT 29 and HCT 116 cells. Ilexgenin A (12.5~50 μM; 24 hours; HT 29 cells) downregulates the expression of SREBP-1, inhibits the translocation of SREBP-1 to the nucleus and decreases the content of TG. Ilexgenin A (12.5~50 μM; HT 29 and HCT 116 cells) induces cell cycle arrest at G1 phase in colon cancer cells. Ilexgenin A (12.5~50 μM; 24 hours; HCT 116 cells) modulates lipid metabolism. Ilexgenin A (50 μM; 24 hours; HT 29 and HCT 116 cells) regulates SREBP-1 by inhibiting HIF1α. Ilexgenin A inhibits fatty acids synthesis. MCE has not independently confirmed the accuracy of these methods. They are for reference only. Cell Viability AssayCell Line: HT 29 and HCT 116 cells Concentration: 0~100 μM Incubation Time: 24 hours Result: Effectively decreased cell viability in HT 29 and HCT 116 cells. Western Blot AnalysisCell Line: HT 29 cells Concentration: 12.5~50 μM Incubation Time: 24 hours Result: Downregulated the expression of SREBP-1. RT-PCRCell Line: HT 29 cells Concentration: 12.5~50 μM Incubation Time: 24 hours Result: Decreased the content of TG. ImmunofluorescenceCell Line: HT 29 cells Concentration: 12.5~50 μM Incubation Time: 24 hours Result: Inhibited the translocation of SREBP-1 to the nucleus.
In Vivo
Ilexgenin A (20 mg/kg) ameliorates the AOM/DSS induced carcinogenesis. Ilexgenin A can regulate lipid metabolism. Ilexgenin A decreases the expression of SREBP-1 and HIF 1α in AOM/DSS mice . MCE has not independently confirmed the accuracy of these methods. They are for reference only.
Ilexgenin A is a pentacyclic triterpenoid, which extracted from Ilex hainanensis Merr. Ilexgenin A can be used for the research of inflammation and cancer.
Condizioni di conservazione di stoccaggio
Protected from light,Store at -80°C
Spedito in
Dry ice packs + Cold packs
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This compound belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.
External Descriptors
Not available
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
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Application Protocols
No validated application protocols were provided for this catalog item. As a general research-use small molecule, protocols are user- and assay-specific.
General handling suggestions:
Stock preparation: Prepare concentrated stocks in dry DMSO (e.g., 10–50 mM). Warm gently (30–40 °C) and sonicate to aid dissolution. Vortex thoroughly.
Working solutions: Dilute stocks into assay medium or mobile phase while keeping final DMSO low (≤0.1–1% v/v typical). Inspect for precipitation; if observed, adjust cosolvent or use surfactants (method-dependent).
Analytical controls: Include solvent blanks, adsorption controls (plastic vs glass), and serial dilutions to assess aggregation-related artifacts.
If intended as an analytical reference:
LC-MS: Optimize ionization mode (APCI/ESI+) and monitor common adducts (e.g., [M+H]+, [M+Na]+). Use a C18 or phenyl-hexyl column; start with high organic (>80% MeOH or ACN with 0.1% FA/NH4OAc) and adjust gradient as needed.
Quantitation: Calibrate with at least 5 concentration levels; evaluate linearity and carryover. Use internal standards where possible.
Please consult the CoA and SDS, and perform small-scale feasibility tests before committing valuable samples.
Biological Roles
No biological/clinical claims are made for this research-use material. The following is general, literature-based context about triterpenoids from Ilex species.
Natural origin: Ilexgenin A is reported as a pentacyclic triterpenoid constituent of Ilex spp. (holly) plants. Such metabolites arise from oxidosqualene cyclization pathways forming oleanane/ursane backbones, followed by site-specific oxidations and decorations.
Putative plant roles (literature/general):
Structural components in cuticular waxes contributing to barrier properties.
Participation in plant defense and allelopathic interactions due to membrane-active hydrophobic scaffolds.
Biochemical properties (general):
Strong hydrophobicity leads to preferential partitioning into lipid bilayers and other hydrophobic domains.
Polar functional groups (e.g., hydroxyl/carboxyl) enable limited H-bonding and potential interactions with proteins or membranes.
Research relevance:
Serves as a reference standard for phytochemical profiling (LC-MS/MS identification in complex botanical matrices).
Useful for studying structure–property relationships of triterpenoid scaffolds, including membrane affinity, aggregation behavior, and binding to lipid-associated proteins.
Important note:
Any biological testing should be designed for in vitro or ex vivo research only and interpreted cautiously, with attention to solubility/aggregation and non-specific adsorption that can confound apparent potency in assay systems.
Buffer Applications
This compound is a hydrophobic small molecule and is not a conventional buffering agent.
Not typically used to establish or maintain pH. No standard buffer systems apply.
For biological assays requiring aqueous buffers, dissolve Ilexgenin A first in a compatible organic cosolvent (e.g., DMSO), then dilute into buffer with careful control of final cosolvent content (≤0.1–1% v/v typically) to avoid precipitation.
Consider adding nonionic surfactants or carrier proteins (e.g., 0.1% Pluronic F-127 or 0.1–0.5% fatty-acid–free BSA) where assay format permits, after appropriate controls, to improve dispersion and reduce nonspecific adsorption.
Green Alternatives
Green chemistry considerations around Ilexgenin A primarily concern solvent choice and derivatization methods, as the molecule itself is a fixed natural product scaffold.
Greener solvent options (general guidance):
Replace chlorinated solvents (DCM, CHCl3) with ethyl acetate, 2-MeTHF, or CPME where reaction scope allows. Many acylations and carbonate formations proceed efficiently in EtOAc or 2-MeTHF with catalytic DMAP.
For dissolution in analytics, consider ethanol or isopropanol as diluents after preparing a concentrated DMSO stock to minimize DMSO content in mobile phases or bioassays.
Oxidation/functionalization alternatives:
Prefer catalytic oxidations (e.g., TEMPO/NaOCl in biphasic systems, oxygen-mediated variants) over stoichiometric chromium(VI) reagents.
Use organocatalytic or enzyme-catalyzed esterifications where feasible (lipase-mediated acylations in green solvents or solvent-free conditions), which can be highly selective for secondary alcohols in triterpenoids.
Workup/waste minimization:
Employ solid-supported reagents (e.g., polymer-supported carbodiimides) to streamline purification and reduce solvent use.
Apply microscale reaction optimization (Design of Experiments) to limit material consumption of rare natural products.
Comparison snapshot (general):
DCM vs 2-MeTHF: similar solvating power for many transformations; 2-MeTHF is bio-based, has a higher boiling point, and lower environmental persistence.
Pyridine vs DMAP + greener bases (e.g., iPr2NEt): replacing neat pyridine with catalytic DMAP in EtOAc can reduce odor/exposure while maintaining rates.
Pharmaceutical Uses
No therapeutic or clinical claims are made. Item-specific pharmacopeial status is not provided.
Potential roles in pharmaceutical R&D (general, research-use only):
Analytical reference standard: for identity/purity benchmarking in botanical raw materials or triterpenoid-enriched extracts (e.g., Ilex spp.).
Preformulation studies: evaluate solubilization approaches for highly lipophilic natural products (co-solvents, lipid-based systems, cyclodextrin inclusion). These studies inform formulation science independent of any therapeutic assertions.
Solid-state characterization: polymorph and amorphous behavior can be explored to understand dissolution performance of rigid hydrophobes.
Regulatory and documentation:
Pharmacopeial monographs: None specified for this item; consult regional compendia if needed.
For any GLP/GMP-adjacent work, obtain the batch CoA and full analytical package (NMR, HRMS, HPLC chromatograms) to support identity and purity verification.
Formulation considerations (general):
Given likely poor aqueous solubility, lipid-based vehicles (oils, SEDDS/SMEDDS) or cyclodextrin complexes are typical investigative tools in preformulation research.
Adsorption to plastics can bias low-dose studies; prefer glassware and low-binding consumables.
Physical Properties
Item-specific specifications were not provided. The following notes distinguish between unspecified catalog data and general literature expectations for pentacyclic triterpenoids like Ilexgenin A.
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: Not specified for this item; refer to CoA/Spec Sheet. (Literature for related triterpenoid aglycones often shows high MPs >200 °C, depending on substitution and crystallinity.)
Boiling point: Not typically applicable (decomposes before boiling under ambient pressure). High-temperature volatility is low (literature, general for triterpenoids).
Density: Not specified for this item; refer to CoA/Spec Sheet.
Refractive index: Not applicable for solids; Not specified for this item.
pKa: Not specified for this item. (General: neutral polyols; carboxylated analogs exhibit acidic pKa in ~4–5 range, literature dependent.)
LogP/logD: Not specified for this item. (General: strongly hydrophobic; calculated logP for many triterpenoids commonly >5, literature.)
Solubility: Not specified for this item; refer to CoA/Spec Sheet. (General guidance: sparingly soluble in water; typically soluble in DMSO, DMF, and moderately in ethanol/MeOH upon warming/sonication; insoluble in highly polar aqueous buffers without cosolvent.)
Practical handling note (general):
For analytical stocks, dissolve by first wetting with a minimal volume of dry DMSO, then dilute with compatible organic solvent. Warm (30–40 °C) and sonicate to aid dissolution; filter (0.22 µm PTFE) for chromatography.
Quality and Grades
Item-specific grade/purity and appearance were not provided in the Product Data.
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Guidance on interpreting grade (general):
Research grade natural product standards are typically accompanied by NMR, HRMS, and HPLC purity data. For use in screening libraries or SAR studies, confirm:
Chromatographic purity (e.g., HPLC/UPLC at multiple wavelengths) and absence of co-eluting isomers.
Identity via 1H/13C NMR, HRMS; where stereochemistry matters, consider NOESY/ROESY or X-ray if crystalline.
Residual solvent content and water (Karl Fischer) as appropriate for solid materials.
If an inhibitor of photodegradation is required, this will be explicitly stated on the CoA; none is specified for this item.
What to expect with Aladdin Scientific items (general best practice):
Each lot’s CoA should list analytical purity, key spectroscopic data, and storage guidance that align with the listing (protected from light, −80 °C).
For quantitative work (bioassays, reference standards), verify potency by exact mass balance: correct weighed mass for residual moisture/solvents if reported on CoA.
Documentation:
For regulatory or QC applications, request supporting analytical package (chromatograms, spectra) to confirm suitability for your method.
Reaction and Applications
This item is positioned for research-use as a small-molecule standard/compound library member. With a pentacyclic triterpenoid scaffold, Ilexgenin A is useful in:
Applications (general for triterpenoids):
Chemical biology probes: serve as a hydrophobic scaffold for SAR exploration by selective derivatization (e.g., at C-3 hydroxyl if present, or carboxyl side chains).
Reference material: method development in LC-UV/LC-MS for plant metabolomics or natural product QC (Ilex species matrices), including retention/mass fingerprinting.
Supramolecular/colloid studies: evaluate micelle or liposome incorporation due to rigid hydrophobic cores.
Esterification/acylation of secondary alcohols: using acid anhydrides or acyl chlorides (DMAP, pyridine or DIC/DMAP systems) to modulate lipophilicity.
Oxidation/reduction: selective oxidation at allylic/secondary alcohol positions (Dess–Martin periodinane, TEMPO/bleach variants) or reduction of ketones (NaBH4, L-Selectride) where present.
Carbamate/urethanation: reaction with isocyanates to introduce H-bonding handles and tuning of membrane affinity.
Late-stage diversification: Mitsunobu (alcohol → various nucleophiles), click handles via carbonate linkers for probe conjugation.
Practical notes:
Protect stereocenters and avoid harsh acidic conditions that can induce rearrangements of polycyclic triterpenoids.
Use anhydrous, oxygen-free conditions when required; many reactions benefit from dry DCM, THF, or toluene. Monitor by TLC with anisaldehyde/sulfuric acid stains to visualize terpenoids.
Reaction Conditions
No item-specific reaction conditions are defined for this catalog entry. The following general conditions are commonly effective for functionalizing triterpenoid aglycones and can be adapted to Ilexgenin A after preliminary solubility testing and small-scale scouting (literature/general guidance):
Esterification/acylation of alcohols:
Reagents: Acyl chloride or anhydride; catalysts: DMAP (5–10 mol%).
Solvent: DCM, EtOAc, 2-MeTHF, or toluene; temperature: 0 °C to rt.
Time: 1–16 h; monitor by TLC/LC-MS. Yields often 70–95% for unhindered sites.
Carbonate/carbamate formation:
Reagents: CDI (1.1–1.5 eq) or DSC; nucleophiles: alcohols/amines.
Solvent: THF, DCM, or EtOAc; temperature: rt to 40 °C.
Oxidation of secondary alcohols:
Reagents: Dess–Martin periodinane (1.3 eq) or TEMPO/NaOCl (cat./stoich.).
Solvent: DCM (DMP) or biphasic CH2Cl2/H2O with buffer (TEMPO); temperature: 0–25 °C.
Quench and promptly purify to avoid overoxidation.
Mitsunobu substitution:
Reagents: DEAD or DIAD, PPh3 (1.2–1.5 eq each); nucleophile: R–XH.
Solvent: THF or toluene; temperature: 0 °C to rt; inert atmosphere recommended.
Hydrogenation (if necessary for side-chain alkenes):
Catalyst: Pd/C (5–10%); solvent: EtOAc/EtOH; temperature/pressure: rt, 1–3 bar H2.
Notes:
Maintain anhydrous conditions where required; many transformations are moisture sensitive.
Given high hydrophobicity, ensure complete dissolution or use phase-transfer strategies; partial suspension can lead to heterogeneous, irreproducible outcomes.
Safety and Handling
Safety information specific to this item was not provided in the listing. Always consult the product SDS for authoritative guidance.
From Product Data (item-specific):
Storage: Protect from light; store at −80 °C.
Shipping: Dry ice packs + cold packs.
GHS 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 laboratory safety guidance for hydrophobic natural products:
PPE: lab coat, safety glasses, and suitable chemically resistant gloves (e.g., nitrile). Avoid inhalation of dust/aerosols; handle powders in a fume hood.
Incompatibilities: Avoid strong oxidizers and strong acids/bases that may degrade sensitive functional groups. Protect from prolonged light and moisture.
Peroxide formation: Not applicable to the solid itself; use fresh, inhibitor-free organic solvents where relevant.
First aid (overview; refer 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; seek medical attention if irritation persists.
Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
Waste: Dispose according to institutional and local regulations for organic chemical waste.
Additional caution:
Many triterpenoids can adsorb strongly to plastics; use glassware for accurate dosing. Prepare concentrated DMSO stocks to minimize handling losses.
Solvent Selection
Ilexgenin A is a highly hydrophobic pentacyclic triterpenoid; water solubility is expected to be very low. The following guidance is general/literature-based for similar triterpenoid aglycones.
Primary solvents for stock solutions:
DMSO: typically the most reliable (e.g., 10–50 mM stocks). Warm (30–40 °C) and sonicate to aid dissolution.
DMF: effective but less preferred for biological assays due to cytotoxicity; suitable for synthetic work.
Ethanol or methanol: moderate solubility; may require warming; avoid high aqueous content to prevent precipitation.
Co-solvent strategies:
For aqueous assays, dilute DMSO stocks into buffer keeping final DMSO ≤0.1–1% v/v, titrating to avoid precipitation.
Add nonionic surfactants (e.g., 0.01–0.1% Tween-80 or Pluronic F-127) as needed for dispersion (method development required; literature guidance).
Polarity/miscibility (general): strong lipophilicity (high logP expected). Not miscible with water; miscible with most aprotic polar organics.
Comparison (general):
DMSO vs ethanol: DMSO yields higher solubility and is less volatile; ethanol offers faster drying and better compatibility with some analytical methods.
Acetone/ACN: limited solubility for bulky triterpenoids; test case-by-case.
Practical tips:
Pre-wet vial walls with a small volume of solvent to minimize adsorption.
For LC-MS quantitation, filter through PTFE; avoid cellulose filters (adsorption risk). Use glass vials with low-adsorption caps/liners.
Storage and Reconstitution
From Product Data (item-specific):
Storage conditions: Protect from light; store at −80 °C.
Shipping: Dry ice packs + cold packs.
General best practices for this compound class:
Container: Store in amber, airtight glass vials with PTFE-lined caps to minimize light exposure and adsorption. Backfill with inert gas (N2/Ar) if long-term storage is anticipated.
Solid storage: Keep desiccated (dry desiccant) to prevent moisture uptake that can affect weighing and stability. Avoid repeated warming/cooling; aliquot on receipt if feasible.
Reconstitution (general guidance):
Solvent: Use dry DMSO for initial dissolution. Target stock concentrations of 10–50 mM based on expected solubility. Warm gently (30–40 °C) and sonicate if needed; do not overheat.
Filtration: If required for analytical work, pass through a 0.22 µm PTFE filter. Rinse filter with a small volume of solvent to minimize loss by adsorption.
Working solutions: Prepare fresh on the day of use. For aqueous media, add DMSO stock slowly under vortexing to minimize precipitation. Verify clarity before use.
Stability notes:
Avoid prolonged exposure to light and air. Return to −80 °C promptly after use.
Freeze–thaw: Minimize cycles by preparing single-use aliquots. If repeated access is required, maintain a −20 °C working aliquot for short-term use (days) and a −80 °C master stock for long-term storage, verifying stability by LC before critical experiments.
Structure and Identity
Brief overview: Ilexgenin A is a plant-derived small molecule classified as a pentacyclic triterpenoid (Ilex spp.). This listing is for a research-use reference/compound library item.
SKU: I648295
Product name: Ilexgenin A
CAS: 108524-94-3
PubChem CID: 21672638 (literature)
InChIKey: 360546 (as provided; appears truncated — consult CoA for the full identifier)
SMILES: 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 features (general/literature description):
Core scaffold: pentacyclic triterpenoid framework (oleanane- or ursane-type topology commonly reported for Ilex metabolites).
Functional groups typically encountered: secondary/tertiary alcohol(s), potential carboxyl or keto functionality, multiple quaternary centers, and extensive aliphatic C–H network.
Stereochemistry: richly stereodefined polycyclic system with multiple chiral centers fixed by the biosynthetic cyclization of squalene/oxidosqualene (literature).
2D structure (verbal depiction; general):
A fused five-ring backbone (A–E rings) with angular methyl groups, one or more oxygenated positions (often at C-3 in triterpenoids), and a short aliphatic side chain at C-17. The dense hydrocarbon skeleton confers strong hydrophobic character with localized polar sites from oxygen substituents.
Notes:
The exact regiochemistry and stereochemistry for Ilexgenin A should be confirmed from a primary spectral reference (CoA, NMR, HRMS) before structure–activity studies or derivatization.
Synthetic Utility
As a densely functionalized, stereochemically rich pentacyclic scaffold, Ilexgenin A provides multiple vectors for late-stage modification and probe development (general/literature perspective for triterpenoids):
Key functional handles (typical):
Secondary/tertiary alcohol(s) at ring junctions (e.g., C-3) suitable for esterification, carbonate/carbamate formation, Mitsunobu inversion/substitution, and oxidative elaboration.
Carboxyl or keto groups (if present) permitting amide/ester formation, reductive amination, or hydrazone/oxime chemistry.
Allylic positions amenable to selective oxidation or halogenation under mild conditions.
Named/representative transformations:
Steglich esterification (DIC/DMAP) to introduce reporter groups or solubilizing tails.
Dess–Martin or TEMPO-mediated oxidations for alcohol → carbonyl, enabling subsequent nucleophilic additions (e.g., Grignard, organocerium) to access analog series.
Mitsunobu coupling to append heterocycles or azides (→ click chemistry) while tuning stereochemistry.
Carbamate/urea linkages via isocyanates or CDI-activated coupling to install H-bond donors/acceptors.
Retrosynthetic value:
Serves as an advanced intermediate/lead for SAR campaigns where preserving the rigid core while exploring periphery substitutions is advantageous for property tuning (lipophilicity, polarity, HBD/HBA counts).
Analytical considerations:
Visualization by TLC may require anisaldehyde/sulfuric acid; LC-MS ionization favors APCI/ESI+ with adduct formation (Na+, NH4+) typical for neutral terpenoids.
Target Specificity
Not applicable. This product is a small molecule natural product and not an antibody, enzyme, or probe with defined biological target specificity provided by the manufacturer.
No antigen/epitope, clone, isotype, or species reactivity information applies.
If used as a chemical probe in research, any target engagement must be established experimentally for the specific system under study and is not specified for this item.
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