Gloriosine , CAS No.7411-12-3

CAS: 7411-12-3 Cat. No.: G667873 Summenformel: C₂₁H₂₃NO₆ Molekulargewicht: 385.4 EG-Nummer: 630-568-0 PubChem CID: 23890

Synonyms

Gloriosine|N-Deacetyl-N-formylcolchicine|N-Formyldeacetylcolchicine|N-Deacetyl-N-formyl Colchicine|N-[(7S)-1,2,3,10-tetramethoxy-9-oxo-6,7-dihydro-5H-benzo[a]heptalen-7-yl]formamide|COLCHICINE, N-DEACETYL-N-FORMYL-|N-Formyldesacetylcolchicine|Formyldescaetylcolchicine, N-|N-Formyl-N-deacetylcolchicine|N-Formyl-Deacetylcolchicine|FORMYLDESACETYLCOLCHICINE, N-|Formamide, N-(5,6,7,9-tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo(a)heptalen-7-yl)-, (S)-|COLCHICINE IMPURITY A [EP IMPURITY]|Gloriosine (N-Deacetyl-N-formyl-colchicin)|Formamide,6,7,9-tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo[a]heptalen-7-yl)-, (S)-|Formamide,N-[(7S)-5,6,7,9-tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo[a]heptalen-7-yl]-|N-[(7S)-1,2,3,10-tetramethoxy-9-oxo-6,7-dihydro-5H-benzo[d]heptalen-7-yl]formamide|FORMAMIDE, N-((7S)-5,6,7,9-TETRAHYDRO-1,2,3,10-TETRAMETHOXY-9-OXOBENZO(A)HEPTALEN-7-YL)-|N-((7S)-5,6,7,9-TETRAHYDRO-1,2,3,10-TETRAMETHOXY-9-OXOBENZO(A)HEPTALEN-7-YL)FORMAMIDE

Storage

Room temperature

Spezifikationen

Synonyme

Gloriosine | N-Deacetyl-N-formylcolchicine | N-Formyldeacetylcolchicine | N-Deacetyl-N-formyl Colchicine | N-[(7S)-1,2,3,10-tetramethoxy-9-oxo-6,7-dihydro-5H-benzo[a]heptalen-7-yl]formamide | COLCHICINE, N-DEACETYL-N-FORMYL- | N-Formyldesacetylcolchicine | Formyldescaetylcolchicine, N- | N-Formyl-N-deacetylcolchicine | N-Formyl-Deacetylco Show more

Storage

Room temperature

Produkteigenschaften

ALogP

1

Namen und Kennungen

Kanonisches Lächeln

COC1=CC=C2C(=CC1=O)C(CCC3=CC(=C(C(=C32)OC)OC)OC)NC=O

IUPAC Name

N-[(7S)-1,2,3,10-tetramethoxy-9-oxo-6,7-dihydro-5H-benzo[a]heptalen-7-yl]formamide

InChIKey

HDSXDWASQCHADG-HNNXBMFYSA-N

INCHI

1S/C21H23NO6/c1-25-17-8-6-13-14(10-16(17)24)15(22-11-23)7-5-12-9-18(26-2)20(27-3)21(28-4)19(12)13/h6,8-11,15H,5,7H2,1-4H3,(H,22,23)/t15-/m0/s1

Isomere SMILES

COC1=CC=C2C(=CC1=O)[C@H](CCC3=CC(=C(C(=C32)OC)OC)OC)NC=O

PubChem CID

23890

Molekulargewicht

385.4

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Hydrocarbon derivatives
    • Klasse Tropones

• Kingdom: Organic compounds
• Superclass: Hydrocarbon derivatives
• Klasse: Tropones
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Tropones
• Alternative Parents: Anisoles Alkyl aryl ethers Secondary carboxylic acid amides Cyclic ketones Organopnictogen compounds Organonitrogen compounds Organic oxides
• Molecular Framework: Aromatic homopolycyclic compounds
• Substituents: Anisole - Tropone - Alkyl aryl ether - Benzenoid - Carboxamide group - Secondary carboxylic acid amide - Cyclic ketone - Ether - Carboxylic acid derivative - Organic oxygen compound - Organooxygen compound - Organonitrogen compound - Organic nitrogen compound - Carbonyl group - Organopnictogen compound - Organic oxide - Aromatic homopolycyclic compound
• Beschreibung: This compound belongs to the class of organic compounds known as tropones. These are compounds containing a tropone ring, which is a cycloheptatrienone ring bearing a ketone group.
• 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

Zugehörige Ziele (menschlich)

BRD4 Tchem Bromodomain-containing protein 4 (0 Activities)

Discover Target: BRD4

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

ACHE Tclin Acetylcholinesterase (18204 Activities)

Discover Target: ACHE

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Zugehörige Ziele (nicht menschlich)

Mus musculus (284745 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

P388 (20296 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

GCN5 Histone acetyltransferase GCN5 (89 Activities)

Discover Target: GCN5

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Wirkungsmechanismen

Chemische und physikalische Eigenschaften

• Molekulargewicht: 385.400 g/mol
• XLogP3: 1.000
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 385.153 Da
• Monoisotopic Mass: 385.153 Da
• Topological Polar Surface Area: 83.100 Ų
• Heavy Atom Count: 28
• Formal Charge: 0
• Complexity: 697.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 1
• 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

No vendor-tested application protocols are specified for this item. The following general-purpose protocols can help standardize handling in chemical biology and analytics.

• DMSO stock preparation:
  • Weigh compound quickly in a low-humidity environment.
  • Prepare 10–50 mM stock in dry DMSO; vortex and sonicate briefly if needed.
  • Aliquot into low-bind microtubes; store desiccated and protected from light.
• LC/UPLC assay check:
  • Dilute a small aliquot to 10–100 µg/mL in initial mobile phase.
  • Run a short gradient on C18; confirm purity and retention time; collect UV and MS traces for your records.
• Plate-based screening (general):
  • Pre-dispense DMSO stocks to assay plates; backfill with buffer to target ≤1% DMSO.
  • Include vehicle controls and a solubility control well; inspect for precipitation.

All procedures should be validated and adapted to your assay and instrumentation. For authoritative instructions, consult your institutional SOPs and the lot-specific CoA/SDS.

Biological Roles

Item-specific biological annotations are not provided in the current listing. The compound is supplied strictly for research use only and not for use in humans or clinical applications.

General literature context:

• Gloriosine has been described in the natural products literature as a plant-derived small molecule (alkaloid class attribution appears in some sources), but precise biological roles and molecular targets should only be ascribed based on verified identity and peer-reviewed references specific to CAS 7411-12-3.
• Natural products in this space may show interactions with cellular pathways; however, any mechanistic claims must be validated experimentally for the exact structure, purity, and form supplied.

Best practices for researchers:

• Treat as an investigational small molecule; establish baseline cytotoxicity and stability in your specific assay format.
• Confirm batch identity/purity prior to mechanistic or omics studies (NMR, HRMS, LC purity), and document concentration by an orthogonal method (e.g., qNMR) to avoid potency misestimation.
• Record solvent and vehicle controls carefully, as apparent biological effects can stem from precipitation or vehicle artifacts.

Note: No medical, diagnostic, or therapeutic use is intended or implied. For any claims regarding target engagement or pathway modulation, cite primary literature tied unambiguously to CAS 7411-12-3 and the same stereochemical form.

Buffer Applications

This product is a discrete small molecule rather than a buffering agent. It is not typically used to formulate buffer systems.

Practical guidance if aqueous use is required:

• Prepare a concentrated DMSO stock and dilute into the desired biological buffer (e.g., PBS, HEPES, Tris) while maintaining a low final organic cosolvent fraction (commonly ≤1% v/v) to minimize assay interference.
• If the compound contains basic nitrogens (as many alkaloids do), transient acidification of the buffer (e.g., 0.05–0.1% formic acid) may improve solubility for analytical injections; ensure compatibility with your assay and stability of the compound.

For true buffering applications (pH control, electrophoresis), use dedicated buffering reagents with known pKa/pH ranges.

Green Alternatives

Because Gloriosine is a specific small molecule used as a research reagent/standard rather than a process solvent, "green alternatives" pertain mainly to the handling solvents and workflow around the compound rather than substitution of the compound itself.

Greener handling strategies (general):

• Solvent choice: Prefer lower-toxicity, greener solvents for dissolution and cleanup when compatible (e.g., ethanol, isopropanol, water-buffer systems) instead of chlorinated solvents. Where high solubility is required, limit DMSO or DMF volumes to the minimum effective amounts.
• Work at microscale: Use microvials and minimal volumes to reduce waste, especially during solubility scouting and analytical runs.
• Purification: Favor reversed-phase chromatography with aqueous-organic systems (e.g., water–MeCN or water–EtOH with volatile buffers) over normal-phase methods using halogenated solvents.
• Energy use: Store at ambient temperature as permitted (Product Data: Room temperature), avoiding unnecessary refrigeration.

Illustrative comparison (general):

• MeCN vs. CH2Cl2 for sample prep: MeCN offers lower environmental persistence and better compatibility with aqueous systems; choose MeCN when it meets analytical needs.
• EtOH/H2O vs. MeOH: Ethanol is considered a greener alcohol and may substitute methanol for some applications if solubility and detection constraints allow.

Always confirm that greener substitutions do not compromise solubility, stability, or analytical performance for your specific lot.

Pharmaceutical Uses

No excipient/functionality or pharmacopeia status is specified for this item. This product is supplied strictly for research use only and is not intended for human or veterinary use.

General context for researchers in preformulation and analytics:

• If used as a research reference standard or tool compound, characterize polymorph/solvate state and confirm moisture content, as these can influence dissolution and apparent potency in in vitro tests.
• For stability studies, assess degradation pathways in candidate vehicles (e.g., ethanol, propylene glycol, PEG 400, aqueous buffers) and set acceptance criteria via stability-indicating HPLC methods.
• If preparing dosing solutions for nonclinical research models (in vitro/in vivo exploratory only within institutional approvals), document vehicle composition, pH/osmolality (if parenteral-like models are explored), and filterability; note that no clinical or therapeutic use is authorized.

Note: Do not infer any therapeutic indications or dosage from this listing. There are no pharmacopeial monographs cited for this product in the current data.

Physical Properties

Item-specific physicochemical specifications are not provided in the current listing.

• 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 applicable/Not typical for characterization of complex alkaloids; refer to CoA/Spec Sheet.
• Density: Not specified for this item; refer to CoA/Spec Sheet.
• Solubility: Not specified for this item; refer to CoA/Spec Sheet.
• LogP, pKa, refractive index: Not specified for this item; refer to CoA/Spec Sheet.

General literature guidance (non-item-specific):

• Naturally occurring alkaloids often display moderate polarity with good solubility in polar aprotic organic solvents (e.g., DMSO, DMF, MeCN) and limited aqueous solubility unless protonated as salts; however, exact values depend on substitution pattern and ionization state.
• If handling for screening, dissolve first in dry DMSO to prepare a high-concentration stock (e.g., 10–50 mM), then dilute into assay buffer with suitable cosolvent while monitoring for precipitation. Verify concentration by UV or quantitative NMR where applicable.

Important: Do not use literature or predicted values as acceptance criteria for this specific lot. For authoritative physical data tied to SKU G667873, consult the lot-specific CoA/SDS.

Quality and Grades

Grade/purity and stabilizers are not specified for this SKU in the current listing.

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

General guidance on interpretation:

• Research-grade small molecules are typically supplied with lot-specific analytical data (e.g., HPLC/UPLC purity, NMR, MS). For library screening or SAR studies, review chromatographic traces for secondary peaks and confirm identity by orthogonal methods as needed.
• If UV-based analytics will be used, request UV/Vis absorbance data to ensure minimal baseline interference in your detection window.
• For bioassay use, consider testing for residual solvents, water content (Karl Fischer), and counter-ion identity (if supplied as a salt), especially where potency normalization is critical.

Recommendations for this item:

• Obtain and archive the lot-specific CoA for SKU G667873 before first use.
• If your application is especially sensitive (e.g., quantitative bioassays, crystallography), consider in-house verification (1H/13C NMR, HRMS, and purity by HPLC with orthogonal methods) and document acceptance criteria in your SOP.

Reaction and Applications

Manufacturer Applications: Not specified for this item in the current listing. This compound is offered within a small-molecule/compound library context and is typically used as a reference standard, screening hit, or chemical probe candidate in research settings (research use only).

Expanded research applications (general, literature-level):

• Chemical biology: As a defined small molecule, it may serve in phenotypic or target-based assays to map structure–activity relationships when paired with analogs.
• Analytical reference: Use as a retention-time and MS reference in plant metabolomics or natural product profiling when supported by authentic spectra for CAS 7411-12-3.
• Derivatization studies: Functional handles in many alkaloids enable preparation of esters, amides, or carbamates to modulate solubility and potency; specific strategies depend on the authenticated structure.

Practical tips:

• Verify identity by orthogonal methods (NMR, HRMS) before in-depth biological testing.
• Prepare fresh solutions or aliquots to minimize degradation; assess stability by LC over the study window.
• For plate-based screens, pre-dilute in DMSO, then distribute to avoid edge effects and solubility artifacts.

Note: Without item-specific structural and reactivity data, do not assume compatibility with strong acids/bases, oxidants, or elevated temperatures; run micro-scale stability checks first.

Reaction Conditions

No item-specific reaction condition data are provided. If you plan transformations on this molecule, adopt a cautious, small-scale, data-driven approach.

General guidance for derivatizing alkaloid-like small molecules (literature-level):

• N-acylation/carbamoylation: Mild base (e.g., DIPEA) in DMF or DCM, 0–25°C, 0.5–12 h, using acyl/ carbamoyl chlorides or activated carbonates. Monitor by LC/MS.
• O-acylation/carbonate formation (if alcohols present): Catalytic DMAP with acyl anhydrides or chloroformates in DCM or MeCN, 0–25°C.
• Reductive amination (if secondary amine-aldehyde pairing applies): NaBH3CN or picoline borane in MeOH/AcOH, 0–25°C, 1–6 h.
• Salt formation for isolation/solubility: Treat free base with HCl, HBr, or organic acids (TFA, fumaric, citric) in suitable solvents; isolate crystalline salts and assay stoichiometry.

Analytical controls:

• Use UPLC with MS detection to monitor conversions and detect minor byproducts; confirm identity by 1H/13C NMR and HRMS.
• Assess stability towards acid/base and light; some natural products undergo rearrangements—conduct stress tests before scale-up.

Note: Conditions above are general, literature-style guidance and may not be appropriate for this exact substance without verification of functional groups and stability.

Safety and Handling

Safety information specific to this item is limited in the current listing; always defer to the SDS for authoritative guidance.

• GHS classification, signal word, pictograms, H-statements: Not specified for this item; refer to SDS.
• General hazard expectations: Many plant-derived alkaloids are bioactive and may be acutely toxic by ingestion, inhalation, or skin contact. Handle as a potentially toxic, irritant organic compound.

Best-practice PPE and engineering controls:

• Use in a certified chemical fume hood.
• Wear lab coat, safety glasses (or face shield for weighing fine powders), and appropriate chemically resistant gloves (e.g., disposable nitrile; change regularly).
• Avoid dust/aerosol generation; if powdered, use antistatic measures and gentle handling.

First-aid overview (general):

• Skin/eye contact: Rinse with copious water for at least 15 minutes; remove contaminated clothing; seek medical attention.
• Inhalation: Move to fresh air; monitor breathing; seek medical attention.
• Ingestion: Rinse mouth; do not induce vomiting; seek immediate medical attention.

Storage and incompatibilities:

• Storage condition (Product Data): Room temperature.
• Keep container tightly closed, protected from light and moisture. Avoid strong oxidizers and strong acids/bases unless stability is documented.

Disposal:

• Dispose of waste as organic hazardous chemical waste according to institutional and regional regulations.

Note: For risk assessment and specific exposure limits, consult the SDS and institutional EHS.

Solvent Selection

Item-specific solubility and polarity parameters are not provided for this product. Selection should therefore be guided by small test dissolutions and your assay constraints.

General guidance for alkaloid-like small molecules (literature-level):

• Primary stock preparation: Dry DMSO is a common first choice for poorly aqueous-soluble bioactives; DMF or MeCN can also be effective. Begin with 10–50 mM trial stocks.
• Aqueous work: If needed in water or buffers, consider forming a dilute DMSO cosolvent mixture (e.g., final 0.1–1% v/v DMSO) while monitoring for precipitation. For basic nitrogen-containing compounds, temporary acidification (e.g., 0.1% formic acid) can increase solubility, provided it suits the downstream application.
• Chromatography prep: For RP-HPLC, dissolve in initial mobile phase or a stronger solvent that is miscible with it; filter through 0.2 µm PTFE or PVDF.

Small comparison (general):

• DMSO: maximal solubilization; compatible with many assays at ≤1% v/v.
• MeOH/EtOH: rapid wetting; volatile; may affect some bioassays above a few percent.
• MeCN: good with many organics; miscible with water; low viscosity; UV cut-off 190 nm.

Ensure solvent choice is validated empirically with a micro-scale test and analytical confirmation (HPLC/UPLC) for your exact lot.

Storage and Reconstitution

• Storage Conditions (Product Data): Room temperature.
• Shipped In: Not specified for this item; refer to CoA/Spec Sheet.
• Appearance: Not specified for this item; refer to CoA/Spec Sheet.

Reconstitution (general guidance):

• For screening/analytical use, reconstitute in dry DMSO to prepare a concentrated stock (e.g., 10–50 mM). Mix thoroughly and, if necessary, briefly sonicate. Record exact concentration based on weight and purity (when available from CoA).
• Prepare single-use aliquots to avoid repeated freeze–thaw and moisture uptake. Store aliquots in airtight vials with desiccant and protect from light.

Stability considerations:

• Without item-specific data, assume sensitivity to moisture, light, and prolonged heat. Minimize exposure during handling. Verify stability over intended use by periodic LC testing.

Freeze–thaw guidance:

• If stocks are kept below ambient (e.g., 2–8°C or −20°C for extended storage per your internal practice), avoid multiple freeze–thaw cycles; thaw at room temperature, mix, and use immediately.

Always consult the lot-specific CoA and SDS for definitive storage, stability, and reconstitution information for SKU G667873.

Structure and Identity

Gloriosine is listed in our small-molecule and compound library category; item-specific structural identifiers are limited in the current product data.

• CAS: 7411-12-3 (Product Data)
• PubChem CID: 23890 (Product Data)
• InChIKey: 118842 (as provided; note this is not a standard 27-character InChIKey format; refer to CoA/SDS for confirmation)
• 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-level context):

• Gloriosine is reported in the natural products literature as an alkaloid constituent associated with Gloriosa spp. and related taxa. Detailed ring system, stereochemistry, and functional group annotation should be taken from an authenticated spectral package or trusted database for the exact registered substance corresponding to CAS 7411-12-3.
• For accurate 2D description (ring fusion, heteroatoms, and stereocenters), consult the item’s Certificate of Analysis (NMR, MS, IR) or authoritative databases keyed to the provided CAS and CID.

Notes for users:

• If you require cheminformatic identifiers (canonical SMILES, InChI, InChIKey), please request the current CoA/Spec Sheet. Ensure that any identifiers you use map unambiguously to CAS 7411-12-3 to avoid mis-annotations in ELNs or screening files.

Synthetic Utility

With limited structure-specific details in the product data, the following guidance focuses on general utility of natural-product-like small molecules in synthesis and method development.

• Reference and benchmarking: Use as a substrate or comparator in chemo-selectivity studies (e.g., site-selective acylation, oxidation, or N-alkylation) if the molecule bears modifiable functional groups typical of alkaloids (tertiary/secondary amines, hydroxyls, amides).
• Derivative generation: Create small libraries of esters, carbamates, or amide conjugates to probe SAR or improve physical properties (solubility, permeability). Ensure that derivatizations preserve the core scaffold for meaningful comparisons.
• Protective group strategy: If nucleophilic heteroatoms are present, consider orthogonal protection (e.g., Boc, Cbz for amines; silyl or carbonate protections for alcohols) to enable stepwise diversification.
• Analytical method development: Use the compound to challenge LC-MS methods (ionization behavior, adduct formation) and evaluate stationary phases (C18, phenyl-hexyl, HILIC) for complex, heteroatom-rich analytes.

Practical notes:

• Confirm the exact structure and stereochemistry (CAS 7411-12-3) before planning transformations.
• Run microscale scouting reactions first and employ LC/MS to map selectivity.
• Maintain a record of spectral data before and after modification to ensure unambiguous structural assignments.

Target Specificity

Not applicable. This product is a small molecule, not an antibody or biologic. No target specificity data (antigen, epitope, species reactivity, clone, isotype) are provided or applicable to this item.

For researchers exploring molecular targets:

• Determine target engagement empirically (e.g., biochemical assays, CETSA/DSF, SPR/ITC) using verified material and appropriate controls.
• Report targets only with supporting primary data tied to CAS 7411-12-3 and documented purity.