This compound belongs to the class of organic compounds known as hexahydrobenzophenanthridine alkaloids. These are alkaloids containing a hexahydrobenzophenanthridine skeleton, which is a tetracyclic compound containing a benzene fused to a hexahydrophenanthridine moiety.
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.
Certificati (CoA, COO, BSE/TSE e tabella di analisi)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Proprietà chimiche e fisiche
Peso molecolare
353.400 g/mol
XLogP3
2.200
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
6
Rotatable Bond Count
0
Exact Mass
353.126 Da
Monoisotopic Mass
353.126 Da
Topological Polar Surface Area
60.400 Ų
Heavy Atom Count
26
Formal Charge
0
Complexity
560.000
Isotope Atom Count
0
Defined Atom Stereocenter Count
0
Undefined Atom Stereocenter Count
3
Defined Bond Stereocenter Count
0
Undefined Bond Stereocenter Count
0
The total count of all stereochemical bonds
0
Covalently-Bonded Unit Count
1
Calcolatori di soluzioni
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Recensioni
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Application Protocols
No tested biological assay protocols are provided for this item. The following general procedures are commonly used when working with small-molecule alkaloids in research settings (literature/general):
Preparation of analytical standard (LC-MS/LC-UV):
Accurately weigh chelidonine in a low-humidity environment.
Dissolve to 1.0 mg/mL in MeOH or ACN (or 1–10 mM in DMSO for MS work).
Prepare serial dilutions in mobile phase (water/MeOH or water/ACN with 0.1% formic acid). Store aliquots at 2–8 °C short-term; check stability.
Bioassay stock solutions:
Dissolve at 10–50 mM in DMSO.
Dilute into culture media or buffer to desired concentration, ensuring final DMSO ≤0.5–1% v/v.
If precipitation occurs, consider mild acidification (e.g., 0.01–0.1% HCl) or use a co-solvent like ethanol (up to 1% v/v total organic).
Solid-phase extraction (SPE) from plant matrices:
Extract ground material with EtOH/H2O (70:30) with 0.1% formic acid.
Wash with water/MeOH; elute with MeOH + 5% NH4OH. Analyze by LC-MS.
Note: These are general frameworks. Optimize concentrations, volumes, and times to your system. Always follow institutional safety practices.
Biological Roles
No item-specific biological data are provided. The following summarizes general/literature context for chelidonine as a plant alkaloid (non-clinical, research-only):
Natural origin: Classified as a benzophenanthridine/isoquinoline alkaloid reported in species such as Chelidonium majus and related Papaveraceae.
Biosynthesis (general): Arises from the benzylisoquinoline pathway; L-tyrosine-derived amines undergo Pictet–Spengler and subsequent oxidative cyclizations and O-methylations to build the polycyclic scaffold.
Chemical properties relevant to biology: The tertiary amine enables protonation near physiological pH, influencing membrane permeability and cellular accumulation. Aromatic methoxy groups contribute to lipophilicity and binding to hydrophobic pockets.
Research uses: Employed as a marker for botanical authentication, metabolic profiling, and chemotaxonomy. Serves as a reference in studies of alkaloid transport, sequestration, and biotransformation in plants and in vitro systems.
Metabolism (in vitro, general): Alkaloids of this class may undergo O-demethylation, N-oxidation, and conjugation (e.g., glucuronidation/sulfation) in microsomal/S9 systems; exact pathways and rates are system-dependent.
Note: No medical or therapeutic claims are made. All information is provided for laboratory research and analytical method development contexts only.
Buffer Applications
Chelidonine is not a buffering reagent. It does not serve as a primary component of common biological or analytical buffer systems.
If preparing aqueous solutions for bioassays or spectroscopy, use standard buffers (e.g., phosphate, acetate, HEPES) and dissolve chelidonine first in a suitable co-solvent (e.g., DMSO or ethanol), then dilute into the buffer while monitoring for precipitation.
Adjusting pH to mildly acidic conditions (e.g., with 0.1% formic or acetic acid) can keep the tertiary amine protonated and enhance apparent aqueous solubility for analytical applications.
For buffer recipes and pH ranges, refer to established buffer references; chelidonine itself is not a buffer component.
Green Alternatives
While chelidonine itself is the target analyte/compound rather than a solvent or reagent, greener choices often pertain to the solvents used in its extraction, purification, and analysis (literature/general):
Greener solvent considerations for handling chelidonine
Replace chlorinated solvents (e.g., CHCl3, DCM) with ethyl acetate or 2-MeTHF where feasible for liquid–liquid extraction and chromatographic purification.
Prefer EtOH or i-PrOH over MeOH for large-scale extraction when compatible with recovery and selectivity.
In analytical LC, reduce acetonitrile use by employing MeOH–water systems or supercritical CO2 (SFC) when appropriate; add low-toxicity modifiers (e.g., CO2 with MeOH containing 0.1% formic acid).
Small comparison (general):
CHCl3 vs EtOAc: EtOAc offers lower toxicity and better biodegradability; may require pH optimization to maintain partitioning of protonated/free-base chelidonine.
MeOH vs EtOH: EtOH is less toxic and renewable; may show slightly different elution strength and viscosity—adjust gradients accordingly.
ACN vs MeOH in LC: ACN often delivers sharper peaks; MeOH is greener but may require longer run times/higher backpressure.
Trade-offs: Greener solvents can alter selectivity and recovery. Validate method performance (recovery, resolution, stability) when transitioning to alternative media.
Pharmaceutical Uses
No item-specific pharmacopeial status or excipient role is provided for this listing, and no clinical/therapeutic claims are made.
Reference standard: Utilized in QC/analytical laboratories for identity/purity testing of botanical raw materials and extracts containing benzophenanthridine alkaloids.
Impurity profiling: May serve as a known comparator/marker in impurity studies of related natural product preparations.
Formulation research: When formulated for in vitro testing, chelidonine is typically dissolved in DMSO/EtOH and diluted into aqueous media; salt formation (e.g., hydrochloride) can be explored to improve aqueous solubility for non-clinical studies.
Regulatory note: This product is supplied strictly for research use only and is not intended for human or veterinary use, diagnostics, or as an active ingredient or excipient in approved drug products.
Physical Properties
Item-specific physical property specifications for this catalog entry are not provided. Where helpful, we summarize commonly reported literature values for chelidonine as general guidance only (not specifications for this item):
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.
• Literature: ~353.37 g/mol for chelidonine.
Molecular Formula (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
• Literature: C20H19NO5.
Melting point (literature): Often reported in the ~130–140 °C range for purified samples; values vary with polymorph/solvate and purity. Use as reference only.
Boiling point: Not typically reported due to decomposition before boiling (literature/general).
Density: Not widely established; consult specific characterization data if required.
Solubility (literature/general):
Poorly soluble in water as a free base; increased solubility in acidic aqueous media (salt forms).
Soluble in polar organic solvents such as methanol, ethanol, DMSO, and chloroform; moderate in acetonitrile.
LogP/LogD (literature estimates): Consistent with a moderately lipophilic alkaloid; specific values vary by source and ionization state. Use experimentally determined values for method development when possible.
pKa (literature/general): One basic center (tertiary amine) typically pKa ~6–8 for related benzophenanthridine alkaloids; exact value should be verified experimentally for chelidonine.
UV-Vis (literature): Strong absorption in the near-UV due to extended conjugation; exact λmax depend on solvent and ionization.
Always confirm working values experimentally under your exact conditions.
Quality and Grades
Grade/Purity (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/Additives (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
Interpretation and implications (general guidance):
For natural products like chelidonine, quality is often documented by NMR identity, HPLC purity/area%, and water/volatile content. In absence of a stated grade, confirm suitability for your application via the CoA and, if needed, independent QC (e.g., qNMR).
If using for quantitative analysis (e.g., as a reference standard), look for traceable purity assessment (100% method, mass balance) and known counter-ion/water content.
If used in bioassays, low levels of residual solvents and well-resolved impurity profiles reduce confounding effects.
For chromatography method development, knowledge of UV cutoff and impurity UV profiles is helpful; if not provided, determine empirically.
Recommendation: Request the lot-specific CoA/SDS for detailed specifications (purity, residual solvents, moisture, optical rotation, and any counter-ion), and verify that they match your intended use (analytical vs. preparative vs. bioassay).
Reaction and Applications
Item-specific application claims are not provided. The following are common research uses for chelidonine as a natural product standard or probe (literature/general):
Analytical standard: Used to develop/validate LC-UV/LC-MS methods for profiling benzophenanthridine/isoquinoline alkaloids in botanical matrices (e.g., Chelidonium spp.). Enables calibration curves, LOD/LOQ determination, and system suitability.
Reference compound in extraction studies: Benchmark for optimizing extraction/partition parameters (solvent selection, pH adjustment to shift between free base and salt forms, solid-phase extraction cleanup conditions).
Spectroscopic characterization: Assignment by 1H/13C NMR, HSQC/HMBC to authenticate plant extracts and to confirm isolation purity.
Chemical derivatization: Formation of salts (e.g., hydrochloride) to enhance aqueous solubility; occasional methylation/acylation studies on phenolic/amine sites to explore structure–property relationships (SAR research).
Chiral analysis: The (+) enantiomer can serve in chiroptical or chiral chromatographic studies to establish enantiomeric excess and absolute configuration (e.g., ECD, optical rotation, chiral HPLC).
Practical tips:
Maintain control of pH during workups—tertiary amine allows switching between organic solubility (free base, basic conditions) and aqueous solubility (protonated, acidic conditions).
Use acidified mobile phases (formic acid, 0.05–0.2%) for improved LC-MS signal stability (protonated molecular ion).
Protect from strong light/oxidants during prolonged analyses to minimize degradation of conjugated systems (general recommendation).
Reaction Conditions
Item-specific reaction conditions are not provided. The following general/literature guidance applies to handling chelidonine in common laboratory contexts:
Stock solution preparation: Dissolve in DMSO or methanol at 10–50 mM; gentle warming (≤40 °C) and sonication can aid dissolution. Filter (0.2 µm PTFE) for analytical use.
LC-MS conditions (analytical, literature): Reverse-phase C18; mobile phase A: water + 0.05–0.2% formic acid, B: acetonitrile or methanol; typical gradient 5–95% B over 10–20 min; detection by UV (near-UV) and positive ESI-MS ([M+H]+). Optimize to resolve from co-occurring alkaloids.
SPE cleanup: Mixed-mode cation exchange (MCX) cartridges exploit the protonated amine; elute with basic organic (e.g., MeOH + 5% NH4OH).
Derivatization examples:
Salt formation: treat with HCl in EtOH/Et2O to precipitate hydrochloride salt.
Demethylation (structure–property studies): BBr3 in DCM at low temperature (caution; literature method), followed by workup under inert conditions.
Stability: Avoid prolonged exposure to strong light/oxidants. Store solutions at 2–8 °C for short-term if necessary; check by LC for degradation.
All conditions should be verified and optimized for the specific matrix, instrument, and performance requirements of your laboratory.
Safety and Handling
Safety information specific to this item is not provided in the listing and should be taken from the product SDS.
GHS Classification (item-specific): Not specified for this item; refer to SDS.
Signal Word / H-Statements / Pictograms (item-specific): Not specified for this item; refer to SDS.
General handling guidance for alkaloid natural products (literature/general):
Toxicological profile: Many benzophenanthridine/isoquinoline alkaloids exhibit bioactivity; avoid inhalation/ingestion/skin exposure. Treat as harmful unless data show otherwise.
PPE: Use lab coat, safety glasses, and appropriate chemically resistant gloves (e.g., nitrile). Handle powders in a fume hood to minimize dust exposure.
Storage: Store tightly closed at the recommended temperature. For this item: Room temperature (per Product Data). Protect from moisture; consider light protection for extended storage of conjugated alkaloids.
Incompatibilities: Strong oxidizers, strong acids/bases may lead to degradation or salt formation; avoid prolonged exposure to reactive reagents. Adsorption losses may occur on basic surfaces (e.g., alumina) for free base.
First aid (overview): If inhaled—fresh air. Skin/eye contact—rinse with water for at least 15 minutes; remove contaminated clothing. If ingested—rinse mouth; do not induce vomiting; seek medical attention. Always follow SDS instructions.
Waste: Collect organic solutions/solids as hazardous chemical waste per institutional and local regulations.
Always defer to the official SDS for authoritative hazard and response information for the supplied lot.
Solvent Selection
Chelidonine, as a moderately lipophilic tertiary amine alkaloid, shows characteristic solubility/ionization behavior that guides solvent choice (literature/general):
Polar protic: Methanol and ethanol typically dissolve chelidonine well; useful for stock solutions for bioassays and spectroscopy. Water solubility is low for the free base but improves markedly upon acidification (formation of water-soluble salts).
Polar aprotic: DMSO and DMF afford high solubility; DMSO is preferred for small-volume bioassay stocks, followed by dilution into aqueous media (watch for precipitation near neutral pH).
Moderately polar: Acetonitrile can dissolve chelidonine at analytical concentrations; commonly used in LC-MS mobile phases with formic acid to stabilize the protonated species.
Nonpolar/halogenated: Limited solubility in hexanes; better in chloroform and dichloromethane for extraction/partitioning tasks.
Selection tips (general):
For analytical LC: Water/ACN (or MeOH) with 0.1% formic acid improves peak shape via protonation; gradient elution resolves co-eluting alkaloids.
For preparative work: Choose solvent systems that consider ionization—e.g., CHCl3/MeOH with a drop of NH3 for free-base behavior on silica; or use reverse-phase for better control.
For bioassay stocks: Prepare 10–50 mM in DMSO, then dilute to working concentrations; keep final DMSO ≤0.5–1% v/v to minimize cell perturbation.
Always verify solubility and stability experimentally under your specific conditions.
Storage and Reconstitution
Storage Conditions (item-specific): Room temperature (per Product Data). Keep container tightly closed in a dry place. For extended stability, many labs store alkaloid standards protected from light; verify with the specific lot’s CoA/SDS.
Shipped In (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
Appearance (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
Reconstitution guidance (general/literature):
Dissolve chelidonine in DMSO, methanol, or ethanol to prepare concentrated stocks (e.g., 10–50 mM). Sonication and mild warming (≤40 °C) may aid dissolution. Filter through 0.2 µm PTFE for analytical work.
For aqueous use, consider preparing acidic aqueous solutions (e.g., with 0.05–0.1% formic or acetic acid) to keep the amine protonated and improve solubility, or form a defined salt (e.g., hydrochloride) prior to dissolution.
Avoid repeated freeze–thaw of solutions; aliquot stocks. For medium-term storage of solutions, refrigeration (2–8 °C) and protection from light are prudent; verify stability by LC before critical experiments.
Always consult the lot-specific CoA/SDS for definitive storage, stability, and handling instructions.
Structure and Identity
Chelidonine (+) is a benzophenanthridine-type isoquinoline alkaloid commonly encountered as a plant secondary metabolite.
SKU: C1067563
Product Name: Chelidonine (+)
CAS: 1235064-12-6 (as provided for this item)
PubChem CID: 10147 (literature)
InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Molecular Formula: Not specified for this item; refer to CoA/Spec Sheet.
• Literature commonly reports chelidonine as C20H19NO5 (for reference only).
Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.
• Literature MW for chelidonine is ~353.37 g/mol (reference only).
Functional groups: Multiple aryl ethers (methoxy substituents), a tertiary amine embedded in an isoquinoline-like ring system, and an amide/lactam-like carbonyl in some depictions depending on tautomeric representation in literature.
Stereochemistry: The “(+)” designation indicates a dextrorotatory enantiomer; chelidonine possesses multiple chiral centers in the saturated portion of the polycyclic system.
2D description in words (literature/general): A rigid, polycyclic aromatic framework containing an embedded nitrogen heterocycle; two to three methoxy groups decorate the aromatic rings, and a saturated bridge bearing stereocenters connects parts of the fused system, conferring helicity and optical activity.
Synthetic Utility
Chelidonine is most often used as a target/analyte rather than as a versatile building block; nevertheless, several synthetic and methodological utilities exist (literature/general):
Chiroptical and chiral method development: The (+) enantiomer can aid in calibrating chiral detection methods (optical rotation, ECD, chiral HPLC), serving as a stereochemically defined reference.
Derivatization chemistry: Phenolic or methoxy sites and the tertiary amine enable targeted modifications—e.g., demethylation/remethylation, acylation, or quaternization—to map structure–property relationships (solubility, lipophilicity) and aid in analytical detection (e.g., permanent charge tags for MS).
Salt formation: Protonation to generate stable salts (HCl, HBr, sulfate) improves handling and aqueous compatibility for process studies or analytical spikes.
Isolation/total synthesis benchmarking: Employed as a reference in method development for natural product isolation and characterization, assisting retrosynthetic planning and spectral verification in synthetic campaigns.
Reactivity considerations (general):
The tertiary amine is nucleophilic under appropriate conditions and readily protonated; avoid over-alkylation unless quaternization is desired.
Aryl ethers are generally robust but can undergo cleavage under strong Lewis acids or BBr3 (for demethylation studies).
The conjugated polycyclic system can be sensitive to strong oxidants; conduct transformations under inert atmosphere when needed.
Target Specificity
This listing is a small-molecule natural product, not an antibody or affinity reagent.
Item-specific target/antigen, epitope, species reactivity, clone, and isotype: Not applicable.
For biochemical studies where chelidonine is used as a probe, any “target specificity” must be determined experimentally for the system under study and is not provided for this product.
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