Dehydrocorydaline nitrate - ≥99% , CAS No.13005-09-9

CAS: 13005-09-9 Cat. No.: D650015 분자식: C₂₂H₂₄N₂O₇ 분자량: 428.44

등급 & 순도 ≥99%

Storage

Store at 2-8°C,Protected from light,Desiccated

Shipped In

Wet ice

개요

Dehydrocorydaline nitrate (13-Methylpalmatine nitrate) is an alkaloid. Dehydrocorydaline regulates protein expression of Bax , Bcl-2 ; activates caspase-7 , caspase-8 , and inactivates PARP Dehydrocorydaline nitrate elevates p38 MAPK activation. Anti-inflammatory and anti-cancer activities. Dehydrocorydaline nitrate shows strong anti-malarial effects ( IC 50 =38 nM), and low cytotoxicity (cell viability > 90%) using P. falciparum 3D7 strain

Form:Solid

IC50& Target:IC50: 38 nM ( P. falciparum 3D7 strain)

사양

사양 및 순도

≥99%

생화학 및 생리적 메커니즘

Dehydrocorydaline nitrate (13-Methylpalmatine nitrate) is an alkaloid. Dehydrocorydaline regulates protein expression of Bax , Bcl-2 ; activates caspase-7 , caspase-8 , and inactivates PARP. Dehydrocorydaline nitrate elevates p38 MAPK activation. Ant

보관 조건

Store at 2-8°C,Protected from light,Desiccated

배송

Wet ice

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작업 유형

INHIBITOR

순수함

≥99%

이름과 식별자

분자량

428.44

화학 및 물리적 특성

• 용해성: DMSO : 50 mg/mL (116.70 mM; Need ultrasonic)

Application Protocols

No manufacturer-validated protocols are provided for this item. The following general procedures are suitable starting points for handling quaternary alkaloid salts in research workflows:

• Stock solution preparation (analytical):

  • Dissolve in DMSO (high-concentration master stock) or in water/methanol (lower concentration working stock). Protect from light. Filter through 0.2 µm PVDF before LC–MS.
  • For aqueous stocks, adjust to pH ~5 with acetate or formate buffer to enhance stability.

• LC–MS method development:

  • Column: C18 or phenyl-hexyl.
  • Mobile phases: A = water + 0.1% formic acid; B = acetonitrile + 0.1% formic acid.
  • Gradient: 5–60% B over 10–20 min as a starting point; detect at UV 280 nm and a visible channel suitable for protoberberines.

• Spectroscopy (UV–Vis):

  • Record spectra in methanol or water; scan 200–600 nm. Dilute to avoid inner-filter effects due to strong visible absorption.

• Biological assay handling:

  • Prepare fresh dilutions immediately before use; verify absence of precipitation upon dilution into assay buffer. Keep DMSO below assay tolerance.

Adjust concentrations/volumes to your application. Refer to CoA/SDS for any item-specific constraints.

Biological Roles

Biological context (literature/general):

• Dehydrocorydaline is a plant-derived protoberberine-type isoquinolinium alkaloid found in species of Corydalis and related genera. In plants, such alkaloids often serve as chemical defense metabolites against herbivores and pathogens and contribute to pigmentation/UV protection due to their chromophoric nature.
• At the molecular level, quaternary isoquinolinium alkaloids are known to interact with nucleic acids, proteins, and membranes via their planar, cationic structures, enabling intercalation-like binding in some systems and electrostatic interactions with polyanionic biomolecules (extent and specificity vary by substitution pattern and conditions).
• In biochemical assays, such compounds are frequently used as tool molecules to probe transporter interactions, efflux mechanisms, and binding to alkaloid-recognizing proteins. Their strong absorbance in the visible region can facilitate spectroscopic tracking in enzymatic or binding studies.

Important notes:

• No medical, therapeutic, or clinical claims are made for this product. It is supplied strictly for research use only.
• Item-specific potency, selectivity, and bioactivity metrics are not provided for this product; consult primary literature for assay design and expected response ranges.
• For cell-based experiments, confirm solubility and non-interference of vehicle (e.g., DMSO) and perform appropriate controls to account for intrinsic color/fluorescence of protoberberines.

Buffer Applications

This product is not a buffering agent. However, buffer choice is relevant for preparing aqueous solutions/samples of quaternary alkaloid salts.

Practical guidance (general):

• pH: Use mildly acidic buffers (pH 4–6) such as acetate or citrate to support solubility and stability; the molecule is permanently cationic, but slightly acidic media can suppress degradation.
• Ionic strength: Moderate ionic strength (10–50 mM) aids reproducibility in binding/biophysical assays without excessive salt that could cause salting-out with co-solvents.
• Additives: 0.01–0.1% acid modifier (formic or acetic acid) is often used in LC–MS sample diluents to improve peak shape and signal stability.
• Filtration: Colored, polyaromatic alkaloids may adsorb to some plastics; use low-binding polypropylene or glass vials and filter through PVDF or PTFE (check compatibility) to remove particulates before analysis.

Recipes and exact concentrations are application-dependent and not specified for this item. Validate your buffer composition empirically for your assay and refer to the CoA/SDS for compatibility boundaries.

Green Alternatives

This item is a target molecule rather than a process solvent; green considerations focus on solvent choices for its handling and analytical workflows.

• Preferred greener media (general guidance):
  • Water (slightly acidified, pH 4–6): Maximizes solubility and minimizes organic solvent use.
  • Bio-based alcohols (ethanol) over methanol or acetonitrile when compatible with the analytical method.
  • Avoid chlorinated solvents (e.g., DCM) which offer little solubility benefit for quaternary salts and have higher environmental burdens.

Comparison (general, literature-informed):

• Water/EtOH: Low toxicity, renewable (EtOH), suitable for prep and spectroscopy; may require acid modifier for stability/solubility.
• MeOH/MeCN: Excellent chromatographic performance, but MeCN has higher EHS concerns and supply volatility; MeOH is toxic and should be minimized when possible.
• DMSO: High solvating power; use sparingly and dispose responsibly; consider propylene carbonate as a greener alternative in some contexts.

Process tips to lower footprint:

• Prepare concentrated stocks to reduce solvent volumes.
• Use UPLC with shorter columns to cut organic solvent consumption.
• Recycle HPLC solvents via in-house distillation when allowed.

Note: No item-specific solvent or impurity specifications are provided; tailor green choices to your method’s performance requirements.

Pharmaceutical Uses

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

Research/manufacturing context (general):

• Reference standard: Can serve as a system suitability or identification standard in natural-product sourcing, botanical extract characterization, and process R&D for plant-derived alkaloids (where permitted).
• Counterion/form selection studies: The nitrate salt can be compared to other counterions to evaluate physicochemical properties (hygroscopicity, crystallinity, dissolution) relevant to preformulation research.
• Analytical development: Useful for establishing LC–UV/Vis or LC–MS methods because protoberberines have strong visible absorbance, allowing dual UV channels for specificity.

Notes:

• No therapeutic claims are made and none should be inferred.
• No pharmacopeial monograph or compliance details are provided for this item; consult CoA/Spec Sheet if available or qualify internally according to your quality system.

Physical Properties

Item-specific physical data

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

Safety-relevant properties

• Hygroscopicity/photolability: Storage guidance indicates to keep desiccated and protected from light, suggesting possible moisture sensitivity and light-induced degradation for the chromophoric protoberberine system (practical note; item-specific stability limits not specified).

Literature/general properties (qualitative)

• Ionic character: Quaternary ammonium nitrate; typically highly polar and water/methanol soluble; often freely soluble in DMSO.
• UV–Vis: Protoberberine alkaloids display strong π–π* absorption in the visible region (yellow to orange solutions) due to extended conjugation (wavelengths vary by substitution; consult literature for exact λmax).
• Acido–basic behavior: Permanently cationic (no acid–base interconversion to a neutral free base under normal conditions).
• Solid-state: Quaternary ammonium nitrates commonly form crystalline, often hygroscopic solids; melting points can be decomposition-prone (report exact MP from CoA where available).

Numerical values such as melting point, density, refractive index, partition coefficients, or solubilities are not specified for this item; refer to CoA/Spec Sheet. Any numerical data needed for method development should be sourced from peer-reviewed literature or measured under your lab’s conditions.

Quality and Grades

Item-specific grade/purity

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

How to interpret grades for alkaloid reference materials (general guidance)

• Research grade: Suitable for discovery biology, method development, and synthetic reference; may not include pharmacopeial certification.
• Analytical/reference grade: Emphasizes identity and purity verification (e.g., HPLC, HRMS, NMR), residual solvent and water content control, and light/moisture stability profiling.
• Counterion specification: For quaternary ammonium alkaloids, the named counterion (nitrate here) should be confirmed by elemental analysis or ion chromatography; counterion content can impact chromatographic behavior and solubility.

Stabilizer/impurity considerations

• Stabilizers: None specified for this item; refer to CoA/Spec Sheet. Products sensitive to light/moisture are typically packaged under inert or desiccated conditions.
• Impurities: Typical related substances for protoberberines include O-demethylated congeners and alternative counterion forms; review the CoA for specific impurity profiles and analytical methods (e.g., HPLC-UV with visible detection).

Always match your application’s requirements (e.g., LC–MS reference, bioassay) to the provided CoA metrics: identity confirmation (NMR/HRMS), purity by HPLC/UPLC, water/LOD, residual solvents, and counterion verification.

Reaction and Applications

Research/analytical applications (typical for this compound class)

• Reference standard: Used as a small-molecule reference for method development in natural products, metabolomics, and alkaloid profiling (e.g., retention time, MS/MS libraries) — item-specific validation parameters not specified.
• Counterion studies: Nitrate form allows evaluation of counterion effects on solubility, crystallinity, and chromatographic behavior vs. chloride or bromide salts.

Chemical manipulation (general synthetic context)

• Counterion exchange (salt metathesis): Nitrate can be exchanged for other anions (Cl−, PF6−, BF4−) using ion-exchange resins or metathesis in polar solvents to tune solubility and crystallinity.
• O-Demethylation/remethylation (on related protoberberines): Literature describes selective demethylation of methoxy groups (e.g., with BBr3 or AlCl3/thiols) followed by etherification for SAR studies; exercise caution due to cationic core sensitivity.
• Redox/photochemical behavior: The extended conjugation supports rich photophysics; light sensitivity suggests handling under low-light during photophysical experiments.

Practical tips

• Minimize light and moisture exposure during reactions and workups.
• For LC–MS quantitation, prepare fresh standards and store aliquots refrigerated, protected from light.
• Use glassware free of basic residues; strong bases can promote side reactions or degradation of quaternary salts.

No specific manufacturer application notes are provided for this item; adapt these general practices to your experimental goals.

Reaction Conditions

General conditions relevant to typical manipulations of quaternary protoberberine salts (literature-informed):

• Counterion exchange (salt metathesis):

  • Solvent: Water, methanol, or ethanol.
  • Reagents: Ion-exchange resin (Cl− form) or addition of a slight excess of the target anion’s salt (e.g., NaCl) followed by precipitation or dialysis.
  • Temperature/time: Ambient temperature; 0.5–4 h contact with resin, monitor by ion chromatography or silver nitrate test (for halides).

• O-Demethylation (on related scaffolds; handle with caution):

  • Reagent: BBr3 in dry DCM is classical for anisoles; for cationic protoberberines, milder demethylation protocols (e.g., AlCl3/thiols) at 0–25°C are reported to mitigate core degradation.
  • Workup: Quench carefully at low temperature; maintain low light exposure and minimize basic conditions.

• Preparative HPLC purification:

  • Mobile phase: Water/acetonitrile with 0.05–0.1% formic or TFA (compatibility with downstream assays should be considered).
  • Detection: 280 nm and a visible wavelength (e.g., 420–450 nm) often provide strong signals for protoberberines.

These are general starting points from literature and practice. Item-specific optimal conditions, reaction scales, and expected yields are not provided for this product and should be determined empirically.

Safety and Handling

GHS/SDS status for this item

• Signal word, hazard statements, pictograms, and classification: Not specified for this item; refer to the product SDS for authoritative information.

General laboratory precautions (good practice)

• PPE: Wear lab coat, safety glasses, and appropriate chemical-resistant gloves. Use in a fume hood to avoid inhalation of dusts/aerosols.
• Avoid generating dust; handle solids with micro-spatulas and antistatic measures.
• Hygiene: Wash hands thoroughly after handling; avoid contact with skin and eyes.

Stability/incompatibilities (general guidance)

• Protect from light and moisture as indicated by storage instructions; store in tightly sealed, light-resistant containers with desiccant.
• Incompatibilities: Strong oxidizers and strong bases/acids may promote degradation or counterion exchange; avoid contact with nitrosating agents. While the nitrate counterion is generally stable in this context, avoid mixing with strong reducing agents or combustible materials in bulk.

First-aid overview (consult SDS for details)

• Inhalation: Move to fresh air; seek medical advice if symptoms persist.
• Skin/eye contact: Rinse with water for several minutes; remove contaminated clothing; obtain medical attention if irritation persists.
• Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.

For spill/leak: Avoid dust formation, collect with inert absorbent or HEPA-equipped vacuum, and dispose of as chemical waste per institutional and local regulations.

Solvent Selection

Polarity and miscibility (general behavior for quaternary protoberberines)

• Primary solvents: Water (acidified), methanol, ethanol, and DMSO typically dissolve quaternary isoquinolinium salts well. Solubility in aprotic, nonpolar media is poor.
• Practical tip: Prepare a concentrated DMSO stock (e.g., for screening) and dilute into aqueous buffers with gentle vortexing; include 0.1–1% co-solvent if needed to prevent precipitation.

Dielectric environment and method development

• Reversed-phase LC: Mobile phases of water/acetonitrile or water/methanol with 0.05–0.1% formic acid enhance peak shape and ionization stability for MS detection.
• Ion-pairing is generally unnecessary due to permanent cationic charge; avoid strongly basic eluents that may promote degradation.

When to choose alternatives

• If protein compatibility is required, use aqueous buffers (pH 5–6) with minimal organic content. For spectroscopic work, methanol or water provides clean UV–Vis backgrounds in the visible region.

Comparison (general)

• Water (acidified): Highest polarity; maximizes solubility and stability; best for bioassays.
• Methanol/ethanol: Good solubility; convenient for spectroscopy and preparative handling.
• DMSO: Highest solvating power; ideal for high-concentration stocks; ensure final DMSO in assays is kept low to avoid interference.

Note: Exact solubility values for this item are not specified; determine empirically under your conditions or consult literature.

Storage and Reconstitution

Item-specific storage/shipping

• Storage conditions: Store at 2–8°C, protected from light, desiccated.
• Shipped on: Wet ice.
• Research use: For research use only.

General reconstitution guidance (not item-specific specifications)

• Allow the vial to equilibrate to room temperature in the dark before opening to minimize moisture condensation.
• Open under low light and dry conditions. If available, handle in a desiccator or glove box with dry air/nitrogen.
• Suggested solvents: Water (slightly acidified), methanol, ethanol, or DMSO. Start with small volumes, vortex, and sonicate briefly if needed. Record exact concentrations gravimetrically.
• For long-term use, prepare single-use aliquots, protect from light (amber vials/foil), and store refrigerated per above conditions. Avoid repeated freeze–thaw of solutions; prefer refrigerated storage of working solutions for short periods and frozen aliquots (light-protected) for longer-term, if stability allows.
• Inspect solutions for discoloration/precipitation prior to use; discard if degradation is suspected.

Exact solution stability, maximum concentration, and shelf-life are not specified for this item; consult the CoA/Spec Sheet and determine stability under your conditions.

Structure and Identity

Item-specific identifiers

• SKU: D650015
• Product name: Dehydrocorydaline nitrate
• CAS: 13005-09-9
• 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.

Literature/structural description (general knowledge)

• Dehydrocorydaline is a quaternary protoberberine-type isoquinolinium alkaloid; the nitrate denotes its counterion as NO3− (salt form).
• Structural features (literature):
  • Tetracyclic, planar, conjugated isoquinolinium core (protoberberine scaffold).
  • Permanently cationic nitrogen (quaternary ammonium), usually accompanied by multiple methoxy substituents on the aromatic rings.
  • The nitrate is an inorganic counterion; alternative counterions (e.g., chloride) are common for this class via ion-exchange.
• 2D structure in words (literature): A fused polycyclic aromatic framework bearing an N-methyl (or N-substituted) isoquinolinium center; several anisole (–OCH3) substituents on the A/D rings; the positive charge is delocalized over the protoberberine system with nitrate balancing charge externally.

Note: Exact stereochemical descriptors and definitive connectivity strings (SMILES/InChI) are not provided with this item; consult the CoA/Spec Sheet or authoritative databases for definitive identifiers.

Synthetic Utility

While dehydrocorydaline nitrate is typically used as a reference alkaloid rather than a building block, chemists may leverage the following features in synthesis and materials studies (general literature-informed guidance):

• Quaternary ammonium center: Permanently charged, enabling ion-exchange to tune solubility and crystallinity. Useful in studying ion-pairing and phase-transfer behaviors.
• Aromatic methoxy groups: Sites for selective O-demethylation, enabling preparation of phenolic derivatives for further derivatization (e.g., etherification, acylation) to probe structure–property relationships.
• Polycyclic, π-rich scaffold: Potential for supramolecular interactions and intercalation studies; can act as a chromophore/reporting unit in conjugates prepared through peripheral modifications (without altering the cationic core).
• Salt metathesis: Exchange nitrate for chloride, bromide, tetrafluoroborate, or hexafluorophosphate to adjust crystallization behavior for single-crystal X-ray or to modify solubility in electrochemical media.

Constraints:

• The cationic core is sensitive to strong bases and nucleophiles that can induce decomposition; conditions should be mild and non-basic.
• The quaternary nature precludes formation of a neutral free base; strategies should focus on peripheral functionalization or counterion manipulation.

Item-specific reactivity data and yields are not provided; consult primary literature and validate conditions at small scale.

Target Specificity

Not applicable. This product is a small-molecule alkaloid, not a biological targeting reagent (e.g., antibody, enzyme, or ligand with validated target specificity provided by the manufacturer).

• No antigen/epitope, species reactivity, clone, or isotype information applies.
• For biochemical or cellular studies, any target engagement must be established independently by the researcher using appropriate controls and orthogonal assays.