Oxoglaucine - ≥98% , CAS No.5574-24-3

CAS: 5574-24-3 Cat. No.: O695290 PubChem CID: 97662

CALIDAD & PUREZA ≥98%

Storage

Room temperature

Especificaciones

Especificaciones y pureza

≥98%

Condiciones de almacenamiento de almacenamiento

Room temperature

Pureza

≥98%

Nombres e identificadores

Sonrisas canónicas

COC1=C(C2=C3C(=C1)C=CN=C3C(=O)C4=CC(=C(C=C42)OC)OC)OC

IUPAC Name

4,5,15,16-tetramethoxy-10-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(17),2,4,6,9,11,13,15-octaen-8-one

InChIKey

ZYKCETVKVRJFGD-UHFFFAOYSA-N

INCHI

1S/C20H17NO5/c1-23-13-8-11-12(9-14(13)24-2)19(22)18-16-10(5-6-21-18)7-15(25-3)20(26-4)17(11)16/h5-9H,1-4H3

Isómeros SMILES

COC1=C(C2=C3C(=C1)C=CN=C3C(=O)C4=CC(=C(C=C42)OC)OC)OC

CAS alternativo

5574-24-3

PubChem CID

97662

Número NSC

141543

Términos de entrada MeSH

oxoglaucine

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Alkaloids and derivatives
    • Clase Aporphines

• Kingdom: Organic compounds
• Superclass: Alkaloids and derivatives
• Clase: Aporphines
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Aporphines
• Alternative Parents: Phenanthrenes and derivatives Benzoquinolines Naphthalenes Isoquinolines and derivatives Aryl ketones Anisoles Alkyl aryl ethers Pyridines and derivatives Heteroaromatic compounds Azacyclic compounds Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Aporphine - Benzoquinoline - Phenanthrene - Isoquinoline - Naphthalene - Quinoline - Anisole - Aryl ketone - Alkyl aryl ether - Pyridine - Benzenoid - Heteroaromatic compound - Ketone - Azacycle - Ether - Organoheterocyclic compound - Organic nitrogen compound - Organooxygen compound - Organonitrogen compound - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Organic oxygen compound - Aromatic heteropolycyclic compound
• Descripción: This compound belongs to the class of organic compounds known as aporphines. These are quinoline alkaloids containing the dibenzo[de,g]quinoline ring system or a dehydrogenated derivative thereof.
• External Descriptors: Not available

Data sources

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.

DOI: 10.1186/s13321-016-0174-y

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APEX1 Tchem DNA-(apurinic or apyrimidinic site) lyase (38016 Activities)

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KDM4E Tchem Lysine-specific demethylase 4D-like (40243 Activities)

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KMT2A Tchem Histone-lysine N-methyltransferase MLL (17327 Activities)

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MBNL1 Tbio Muscleblind-like protein 1 (34431 Activities)

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Mapk1 MAP kinase ERK2 (650 Activities)

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Mecanismos de acción

Propiedades químicas y físicas

• Peso molecular: 351.400 g/mol
• XLogP3: 3.500
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 351.111 Da
• Monoisotopic Mass: 351.111 Da
• Topological Polar Surface Area: 66.900 Ų
• Heavy Atom Count: 26
• Formal Charge: 0
• Complexity: 528.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Application Protocols

• Item-specific (Product Data)

  • No validated protocols are provided for this item.

• General laboratory protocols (illustrative; adjust to your system)

  • Preparation of analytical stock solution
    • Weigh the required amount quickly in a low-humidity environment.
    • Dissolve to 10 mM in anhydrous DMSO or methanol. Sonicate briefly if needed. Store aliquots in amber vials to minimize light exposure.
  • RP-HPLC assay (general starting point)
    • Column: C18, 150 × 4.6 mm, 5 µm.
    • Mobile phase: A = water + 0.1% formic acid; B = acetonitrile.
    • Gradient: 20% to 70% B over 20 min; flow 1.0 mL/min; detection at 254 and 280–320 nm.
    • Inject a 0.1–0.5 mg/mL sample in MeOH or initial mobile phase.
  • LC–MS check
    • Use volatile acids (formic/acetic) only. Avoid non-volatile buffers. Scan in positive ESI due to tertiary amine; adjust cone voltage to maximize [M+H]+ signal.

• Notes

  • Verify solubility and stability in the chosen solvent before long-term storage. For quantitative work, prepare fresh solutions or use validated stability-indicating methods.

Biological Roles

• Scope: No biological data are provided in the product entry. The following are general literature-oriented notes on isoquinoline/aporphine alkaloids and should not be construed as clinical claims.

• Literature/general context

  • Source: Oxidized derivatives of aporphine alkaloids (such as oxoglaucine) have been reported from certain plant taxa within the Annonaceae and related families. Isolation typically follows alkaloid-targeted extraction and chromatographic purification.
  • Biochemical behavior: Tertiary amine-containing alkaloids are protonated under physiological pH and can interact with biomacromolecules via cation–π and hydrogen-bonding interactions. Methoxy/phenolic groups modulate lipophilicity and membrane permeability.
  • Metabolism: Common metabolic pathways include O-demethylation, N-oxidation, and conjugation (glucuronidation/sulfation) catalyzed by hepatic enzymes (general for aporphines).

• Research use examples

  • Employed as a reference material in phytochemical surveys, metabolomics libraries, and method validation for LC–MS/MS quantification of plant alkaloids.
  • Utilized as a probe to study structure–property relationships (ionization, permeability, and binding) within polycyclic aromatic alkaloids.

• Important disclaimer

  • No medical, diagnostic, or therapeutic use is intended or implied. For research use only, as stated in the Product Data.

Buffer Applications

• Not typically applicable. Oxoglaucine is a small-molecule alkaloid, not a buffering agent. It does not define a conventional buffer system.
• Practical note: When preparing aqueous solutions, acidic buffers (e.g., acetate, citrate, or formate at pH 3–5) can aid solubilization by protonating the tertiary amine (general guidance). Select buffer components compatible with your analytical detection (e.g., volatile buffers for LC–MS).

Green Alternatives

• Context: While oxoglaucine itself is a target analyte/compound, greener choices primarily concern solvent and reagent selection for its handling, separation, and derivatization.

• Greener solvent substitutions (literature/general)

  • Replace chlorinated solvents (DCM/CHCl3) with ethyl acetate, 2-methyltetrahydrofuran (2-MeTHF), or dimethyl carbonate (where compatible with solubility and reaction requirements).
  • Prefer ethanol or methanol over acetonitrile where chromatographic performance allows.
  • For acid–base liquid–liquid extractions, use ethyl acetate/MTBE rather than DCM where phase behavior is acceptable.

• Greener reagents for common transformations

  • O-Demethylation: avoid large excesses of BBr3 when possible; consider AlCl3/thiol systems or catalytic demethylations reported with ionic liquids or deep eutectic solvents (emerging literature), balancing selectivity.
  • Oxidations: employ H2O2/urea or O2 with suitable catalysts instead of stoichiometric peracids when feasible.

• Comparison snapshot (general)

  • DCM vs 2-MeTHF: 2-MeTHF offers lower toxicity and bio-based sourcing; may require slightly elevated temperatures to match solubility and has a distinct odor.
  • ACN vs EtOH: ethanol is renewable and less toxic but may reduce chromatographic resolution; pressure may increase on RP columns.

• Waste minimization

  • Implement micro-scale reactions, SPE cleanup over repeated LLE, and recycle high-purity solvents with in-lab distillation where policy permits.

Pharmaceutical Uses

• Item-specific (Product Data)

  • No pharmacopeial or formulation information is provided for this item.

• Literature/general (non-clinical)

  • Role in development workflows: may be used as a reference standard or impurity marker in natural-product-derived materials. Suitable for method development and validation (e.g., specificity, linearity, precision) in QC of botanical extracts.
  • Excipients/processing aids: not used as an excipient to the best of general knowledge; rather, it serves as a characterized analyte in research settings.

• Compliance and handling

  • For research use only (per Product Data). Not for human or veterinary use. Any use in GMP settings would require independent qualification and verification of identity, purity, and stability, which are not specified here.

Physical Properties

• Item-specific (Product Data)

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

• Literature/general properties (typical for aporphine-type alkaloids; verify for oxoglaucine specifically)

  • Physical state: usually isolated as a solid; free base often crystalline or amorphous; salts (e.g., HCl) are typically more crystalline.
  • Solubility: poor in water as free base; enhanced solubility in polar organic solvents (MeOH, EtOH, acetonitrile) and in DMSO; readily soluble in dilute aqueous acid as protonated salts.
  • Acid–base behavior: tertiary amine with pKa (conjugate acid) commonly in the 6–9 range for aporphines (literature, compound-class trend); expect increased aqueous solubility upon acidification.
  • Partitioning: lipophilic in free-base form (high logP typical for poly-methoxy aromatics; literature, class trend).
  • UV–Vis: aromatic chromophores and methoxy substituents typically afford strong UV absorbance in 230–290 nm region; additional bands possible near 320–360 nm depending on substitution (literature, class trend).
  • Melting/boiling point, density, refractive index: Not specified for this item; refer to CoA/Spec Sheet.

• Practical analytical notes

  • HPLC detection at 254 nm and/or 280–330 nm is commonly effective for isoquinoline alkaloids (literature practice). Adjust based on actual spectrum of this lot.

Quality and Grades

• Item-specific (Product Data)

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

• Guidance on interpreting grade (general)

  • Research grade natural products are commonly specified by HPLC purity (area %) with accompanying chromatogram and UV trace. When available, review spectroscopic identity confirmation (1H/13C NMR, HRMS) and residual solvent profile.
  • If supplied as a salt (e.g., hydrochloride), assay may be reported on an anhydrous/free-base basis—confirm basis before calculating molar quantities.
  • Low-UV or LC–MS grade solvents and reconstitution reagents are recommended for trace analysis. For bioassay or metabolomics workflows, consider additional testing for residual metals or peroxide-forming impurities when relevant.

• What to check on the CoA for this item

  • Exact structural assignment (name-to-structure mapping), counterion (if any), purity method and wavelength, water/volatiles content (KF/TGA), residual solvents, and any stabilizers. If values are not present, request a detailed specification sheet.

Reaction and Applications

• Item-specific (Product Data)

  • Manufacturer applications: Not specified for this item.

• Research applications (literature/general)

  • Reference standard: used in phytochemical profiling, dereplication, and quantitative assays of plant extracts containing aporphine/isoquinoline alkaloids.
  • Probe compound: suitable for studying oxidative metabolism (e.g., O-demethylation, N-oxidation) using microsomal or chemical models due to its methoxy- and tertiary-amine functionalities.
  • Photophysical/analytical: aromatic chromophores enable UV–Vis and fluorescence screening for binding or partition studies.

• Chemistry context

  • Functional handles: aryl methoxy groups (subject to demethylation), tertiary amine (salt formation, quaternization), aromatic rings (electrophilic substitution under controlled conditions), potential benzylic positions (oxidation/reduction).
  • Derivatization:
    • O-Demethylation (BBr3, AlCl3/thiols, or Lewis acid-mediated) to access phenols for further coupling (e.g., Mitsunobu, carbamate formation).
    • N-oxidation (m-CPBA) followed by Polonovski-type rearrangements to probe structure–activity or modulate polarity.
    • Electrophilic aromatic substitution on activated rings (nitration/halogenation) with attention to deactivation by the “oxo” substituent.

• Practical tips

  • Use anhydrous, oxygen-controlled conditions for sensitive transformations; protect methoxy-rich substrates from strong acids at elevated temperature to avoid decomposition.
  • For analytics, co-inject authentic standards and monitor multiple wavelengths to differentiate closely eluting alkaloids.

Reaction Conditions

• General guidance (literature; adapt to oxoglaucine after confirming exact structure)

  • O-Demethylation: BBr3 (1–3 equiv per methoxy) in dry DCM at −78 to 0 °C, then warm to RT; quench carefully with MeOH/H2O. Typical times: 1–12 h depending on substitution. Competing demethylations may occur—monitor by LC–MS.
  • N-oxidation: m-CPBA (1.1–1.5 equiv) in DCM or CHCl3 at 0–25 °C for 1–3 h affords the N-oxide; neutralize residual peracid with aqueous Na2S2O3.
  • Electrophilic aromatic substitution: Nitration or halogenation under mild conditions (AcOH/HNO3, NBS/NCS) can be feasible on activated rings; protect sensitive phenols if present.
  • Salt formation/crystallization: dissolve free base in minimal EtOAc or MeOH and treat with anhydrous HCl in dioxane or gaseous HCl to precipitate the hydrochloride salt; isolate by filtration and dry under vacuum.

• Solvent/atmosphere

  • Use anhydrous solvents and inert atmosphere (N2/Ar) for Lewis-acid-mediated steps. Protect from prolonged light/air to minimize oxidative degradation.

• Yields and kinetics

  • Reported yields for analogous aporphine manipulations vary widely (40–90%) depending on substitution and conditions (literature, general). Optimize stoichiometry and temperature, and employ TLC/LC–MS to avoid overreaction.

• Safety

  • Handle BBr3 and peracids with appropriate controls (dry glassware, fume hood, low-temperature quench). Carefully manage exotherms during acid gas salt formation.

Safety and Handling

• Item-specific (Product Data)

  • GHS classification: Not specified for this item; refer to SDS.
  • Signal word: Not specified for this item; refer to SDS.
  • Hazard statements: Not specified for this item; refer to SDS.
  • Pictograms: Not specified for this item; refer to SDS.
  • Storage conditions: Room temperature (per product data).

• General safety guidance (literature/general; not a substitute for SDS)

  • Potential hazards: small-molecule alkaloids can present acute toxicity, skin/eye irritation, or specific organ toxicity; handle as potentially harmful. Avoid inhalation/ingestion and contact with skin/eyes.
  • PPE: lab coat, safety glasses, and appropriate chemical-resistant gloves (e.g., nitrile). Use in a fume hood to prevent inhalation of dust or solvent vapors.
  • First aid overview: in case of exposure, rinse affected area with water for ≥15 min; remove contaminated clothing; seek medical attention. If inhaled, move to fresh air; if ingested, do not induce vomiting—seek medical care. Follow SDS instructions.
  • Handling: minimize dust generation; employ antistatic measures when weighing fine powders. For solution handling, cap vials promptly and avoid light/air exposure where degradation is a concern.
  • Incompatibilities: strong oxidants may react with phenolic/amine functionalities; strong bases/acids may induce decomposition under forcing conditions. Store away from oxidizers and moisture unless stored as a defined salt.
  • Waste: dispose according to institutional hazardous waste protocols for organic, nitrogen-containing compounds.

Solvent Selection

• Applicability: Oxoglaucine is a neutral/tertiary-amine-containing aromatic alkaloid. Solvent choice is typically driven by intended use (analytical vs. synthesis) and by the desired ionization state.

• Practical guidance (literature/general)

  • Stock solutions for analytics: DMSO or methanol are robust first choices due to high solvating power for poly-methoxy aromatics. For LC–MS, methanol or acetonitrile with 0.1% formic acid can improve peak shape by suppressing on-column interactions.
  • Aqueous work: Poor water solubility is expected for the free base. Prepare acidic aqueous solutions (e.g., 0.01–0.1 M HCl) to form a soluble ammonium salt when required.
  • Partitioning/purification: Ethyl acetate, dichloromethane, or MTBE often extract the free base efficiently; switch to aqueous acid–base partitioning to toggle solubility during workups.
  • Solid-phase cleanup: Strong cation-exchange (SCX) cartridges retain protonated alkaloids; elute with basic organic mixtures (e.g., MeOH + NH4OH).

• Comparative solvent notes

  • DMSO vs MeOH: DMSO offers highest solubility; MeOH is more volatile and LC–MS friendly.
  • ACN vs MeOH (HPLC): ACN tends to give lower backpressure and sharper peaks but is costlier; MeOH is greener and less expensive.

• Non-applicability

  • No specific solvent spec is provided for this item; the above are general recommendations to be validated in your method.

Storage and Reconstitution

• Item-specific (Product Data)

  • Storage conditions: Room temperature.
  • Shipped in: Not specified for this item; refer to CoA/Spec Sheet.

• General best practices (literature/general)

  • Solid storage: keep tightly capped in a desiccated environment, protected from light. Many methoxy-rich aromatics are light/air sensitive over long periods; amber glass and inert-gas headspace are advisable for archival storage.
  • Reconstitution: dissolve in dry DMSO or methanol to prepare concentrated stocks (e.g., 10–50 mM). Filter through a PTFE syringe filter (0.2 µm) for analytical use. For aqueous applications, acidify to form a soluble salt as needed.
  • Freeze–thaw: for DMSO or MeOH stocks, aliquot to avoid repeated freeze–thaw cycles. Store DMSO stocks at −20 °C and protect from moisture to prevent dilution by absorbed water (general recommendation; not specified for this item).
  • Stability monitoring: periodically verify by HPLC/LC–MS for degradation (demethylation/oxidation) if stored for extended periods.

• Disclaimer

  • Where specific stability limits, water content, and impurity specifications are required, consult the product’s Certificate of Analysis and SDS. Values not provided above are: Not specified for this item; refer to CoA/Spec Sheet.

Structure and Identity

• Item-specific (Product Data)

  • SKU: O695290
  • Product name: Oxoglaucine
  • CAS: 5574-24-3
  • PubChem CID: 97662
  • InChIKey (as provided): 469714
  • 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.

• Literature/general identity (for reference only; verify against primary sources before use)

  • Compound class: aporphine/isoquinoline-type plant alkaloid (oxidized derivative of glaucine).
  • Structural features (descriptive): polycyclic tetracyclic isoquinoline-derived scaffold with multiple aromatic rings; typically contains several methoxy substituents and one additional carbonyl functionality relative to glaucine (“oxo-” derivative). No stereocenters are expected in fully aromatic aporphine frameworks; partially hydrogenated variants can present axial chirality—confirm for the exact structure from primary data.
  • 2D description in words: fused benzoisoquinoline core (aporphine-type) bearing methoxy substituents on the aromatic ring system; one ring carries a ketone (oxo) functionality; tertiary nitrogen embedded in the heteroaromatic/aza ring (protonatable under acidic conditions).

• Notes

  • The precise constitutional isomerism and stereochemical state must be confirmed from the Certificate of Analysis or an authenticated spectral dataset (1H/13C NMR, HRMS).

Synthetic Utility

• Strategic value (literature/general)

  • Oxoglaucine represents an oxidized aporphine scaffold, offering a platform for SAR elaboration on a rigid polycyclic framework. The tertiary amine, aryl methoxy groups, and an “oxo” moiety enable orthogonal transformations.

• Representative transformations and tactics

  • Amine chemistry: salt formation (HCl, HBr) for crystallization/purification; quaternization (MeI, MeOTf) to tune solubility and reactivity; N-oxide formation (m-CPBA) for directed rearrangements.
  • O-Demethylation: selective BBr3-mediated demethylation to phenols; subsequent etherification/esterification enables linker installation.
  • Cross-coupling handles: after halogenation of activated aryl positions, Suzuki or Buchwald–Hartwig couplings can diversify substitution (requires prior installation of halogens).
  • Oxidation/reduction: benzylic or ring-activated positions may be addressed with mild oxidants or hydrogenation; the “oxo” group can participate in acylation chemistry or be reduced to alcohols depending on position (verify structure before planning).

• Retrosynthetic considerations

  • Access via oxidative modification of glaucine or de novo assembly of the aporphine core (e.g., Bischler–Napieralski/Pictet–Spengler sequences followed by oxidative cyclizations) is reported in the aporphine literature; these routes inform derivatization strategies for oxoglaucine analogs.

Target Specificity

• Not applicable. This product is a small-molecule alkaloid, not a biological targeting reagent or antibody. No antigen/epitope, clone, isotype, or species reactivity information applies.