Δ9-THCQ , CAS No.860480-30-4

CAS: 860480-30-4 Cat. No.: T1442253 Fórmula: C₂₁H₂₈O₃ Peso molecular: 328.45

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Descripción general

Δ9-THCQ (Δ9-Tetrahydrocannabinoquinone) is an oxidative byproduct of Δ9-THC.

Specifications

Condiciones de almacenamiento de almacenamiento

Store at -20°C

Enviado en

Ice chest + Ice pads

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Nombres e identificadores

• Peso molecular: 328.45

Application Protocols

No tested biological assay protocols (e.g., WB, IHC, IF, FC) or recommended dilutions are provided for this small-molecule product.

General handling protocol for preparing research stocks (not product-specific):

• Allow the vial to equilibrate to room temperature in a desiccator before opening to avoid moisture condensation.
• Rapidly weigh the required amount in a fume hood. Reseal promptly.
• Prepare a concentrated stock solution in dry DMSO or acetonitrile (e.g., 10–50 mM). Filter through a PTFE syringe filter (0.2 µm) if particulates are present.
• Aliquot into amber, airtight vials under inert gas (N2 or Ar) to minimize light/oxygen exposure. Store at −20 °C or as indicated on the label.
• For aqueous applications, dilute the organic stock immediately before use with vigorous mixing; verify that no precipitation occurs at working concentrations.

These are general best practices. For authoritative guidance, consult your institution’s SOPs and the product’s CoA/SDS.

Biological Roles

No biological, clinical, or therapeutic claims are made for this product. The following content is general literature context only and not specific to SKU T1442253.

• Cannabinoid-derived quinones reported in the literature have been used as chemical tools to explore redox biology and electrophile sensing pathways because quinone motifs can undergo reversible two-electron redox cycling and form covalent adducts with nucleophilic residues (e.g., cysteine) in proteins and peptides.
• In contrast to phenolic cannabinoids, quinone conversion often increases electrophilicity and alters lipophilicity and photophysics, which can change membrane association and noncovalent binding profiles in model systems.
• Quinone-containing probes are frequently used to interrogate cellular oxidative stress responses (e.g., glutathione conjugation capacity) and to map nucleophile-reactive hotspots using chemoproteomics. Such applications are conducted under research conditions with appropriate controls and do not imply biological activity for this specific item.
• The pronounced UV–vis absorbance of quinones facilitates tracking uptake/partitioning in model membranes or in vitro systems by HPLC–UV or spectrophotometry.

Any characterization of biochemical interactions for this specific product should be determined empirically in your laboratory. Consult the SDS for any hazard statements relevant to biological handling. Research use only.

Buffer Applications

This product is a hydrophobic small molecule and is not a conventional buffering agent. Therefore, buffer preparation and pH-control applications are not typically applicable.

Practical notes for assay use (general guidance):

• If used in aqueous buffers, prepare concentrated stocks in DMSO or acetonitrile and dilute into the buffer immediately before use with vigorous mixing to avoid precipitation. Keep final organic co-solvent fractions low (typically ≤0.1–0.5% v/v) to maintain biological system integrity, if applicable.
• Use solubilizing aids where permitted (e.g., non-ionic surfactants at low percentages or carrier proteins) and pre-screen for compatibility.

No item-specific buffer system data are provided for SKU T1442253.

Green Alternatives

Environmental and safety considerations (general)

• Quinone-containing aromatic molecules may necessitate chlorinated solvents and can be redox-active. Greener handling focuses on solvent selection, scale minimization, and waste reduction rather than altering the molecule itself.

Greener solvent choices (relative to common practices; literature guidance)

• Prefer ethyl acetate, 2-MeTHF, cyclopentyl methyl ether (CPME), or toluene over dichloromethane/chloroform when feasible. Use acetonitrile or ethanol/isopropanol where solubility permits.

Example comparison (general; not product-specific)

• DCM vs 2-MeTHF/CPME: Ether solvents offer lower environmental impact and easier recycling; they may alter reactivity with nucleophiles—evaluate on small scale.
• MeCN vs DMF/DMSO: MeCN is easier to remove and has a favorable EHS profile relative to DMF; DMSO remains valuable for stock solutions but consider minimal volumes.

Operational green tips

• Run microscale reactions and use high-throughput purification (analytical HPLC scouting) to minimize solvent.
• Apply LED or ambient-temperature conditions where compatible; avoid prolonged photolysis that could degrade quinones.
• Capture and re-use silica or switch to greener purification (crystallization, liquid–liquid extraction) when possible.

These are general green-chemistry practices for working with hydrophobic, redox-active small molecules such as cannabinoid quinones.

Pharmaceutical Uses

No excipient or pharmacopeial status is provided for this item. This product is supplied strictly for research use only and is not intended for human or veterinary use, diagnostic procedures, or clinical applications.

General formulation context (literature-based, not product-specific):

• Hydrophobic small molecules like cannabinoid quinones, when studied in formulation R&D, are often handled using co-solvent systems (e.g., ethanol/propylene glycol/water), lipid vehicles, or polymeric carriers to evaluate physicochemical behavior. These activities remain strictly preclinical/research.
• Strong chromophores (quinone motifs) can interfere with UV-based quantitation in complex matrices; validated HPLC or LC–MS methods with appropriate internal standards are recommended for formulation studies.

For any regulated use, consult relevant pharmacopeial monographs and regulatory guidance—none apply here for SKU T1442253 based on the provided Product Data.

Physical Properties

Item-specific specifications

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
• Density, refractive index, logP, pKa, melting point, boiling point, UV cutoff, water/peroxide/metal limits: Not specified for this item; refer to CoA/Spec Sheet.

General/literature expectations for cannabinoid quinones (for planning only; not product specs)

• Physical state: Often solid or glassy solid; intensely colored (yellow to deep red/brown) due to the quinonoid chromophore.
• Solubility profile: Poorly soluble in water; typically soluble in organic solvents such as DMSO, DMF, acetone, ethyl acetate, dichloromethane, chloroform, toluene, and alcohols; highest stability and solubility for stock solutions commonly achieved in dry, oxygen-limited DMSO or MeCN. Exact solubility for this item is not specified.
• UV–vis: Quinone chromophores usually show strong absorption in the near-UV/visible region with bands around 240–280 nm and 380–450 nm (literature, chromophore-dependent). Useful for monitoring reactions and purity by HPLC–UV. Not product-specific.
• Stability considerations: Quinones can undergo redox reactions, nucleophilic additions, and light/air-induced transformations. Samples are commonly handled under subdued light and with minimal air/moisture exposure. These are general best practices; confirm stability for this item from the CoA/SDS.

Always treat the above as contextual literature guidance only; rely on the item’s CoA/Spec Sheet/SDS for definitive properties.

Quality and Grades

Item-specific quality information

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

How to interpret common grades (general guidance)

• Research grade: Suitable for discovery chemistry, screening, and non-GLP experiments. Purity typically assessed by HPLC/LC–MS and/or NMR; the acceptance criteria vary by supplier. If the item is intended for screening libraries, low UV background and defined identity by HRMS/NMR are typical but must be confirmed on the CoA.
• Stabilizers/inhibitors: Not specified for this item. Many quinones are shipped neat without stabilizers; if a stabilizer is used, it will be listed on the CoA and may influence downstream reactions or bioassays.

Recommended quality checks upon receipt (best practice)

• Verify identity by LC–MS (m/z of molecular ion/adduct), and, if needed, 1H/13C NMR in an aprotic solvent (e.g., CDCl3, DMSO-d6). Quinone carbonyls give characteristic 13C shifts (~180–190 ppm, literature).
• Assess purity by HPLC–UV at multiple wavelengths (e.g., 254/280/360–420 nm) to capture quinonoid absorbance and possible aromatic impurities.
• Document water content only if relevant to your application; no Karl Fischer spec is provided for this item.

Always defer to the product’s CoA/Spec Sheet for the definitive grade, assay method, and acceptance limits.

Reaction and Applications

Scope of use (research only)

• Δ9-THCQ is supplied as a small-molecule research reagent within a compound library. While item-specific application notes are not provided, quinone-bearing cannabinoids are used in discovery chemistry, redox studies, covalent probe development, and as electrophilic scaffolds in medicinal chemistry.

Representative reaction families leveraging quinone functionality (literature-based, not product-specific)

• Conjugate (Michael) additions: Soft nucleophiles (thiols, amines) add to the conjugated diketone system, enabling diversification (e.g., S- or N-adduct libraries).
• Redox transformations: Reversible interconversion with hydroquinones under mild reducing conditions (Na2S2O4, ascorbate, metal hydrides), providing redox-responsive systems.
• Cycloadditions and annulations: o- or p-Quinones can engage in Diels–Alder reactions with dienes to furnish bicyclic adducts (useful for scaffold elaboration).
• Cross-coupling on aryl handles (if present): Suzuki–Miyaura, Buchwald–Hartwig, or Sonogashira couplings when the cannabinoid framework carries a halide/boronate—structure-dependent.

Analytical/assay applications (general)

• Redox and covalency profiling: The quinone chromophore is UV–vis active and electrophilic, enabling LC–MS tracking of adducts with biological nucleophiles (GSH, cysteine peptides) and kinetic characterization.

Note: No item-specific “Manufacturer Applications” are provided for SKU T1442253. The above represents general chemistries typical of quinone-containing small molecules.

Reaction Conditions

The following are general, literature-based conditions for quinone transformations and are not specifications for this item. Optimize on small scale.

• 1,4-Addition (thiols/amines): Quinone (1.0 eq), nucleophile (1.0–2.0 eq), base catalyst (e.g., Et3N, DBU 5–20 mol%) or none, solvent DCM/MeOH/MeCN, 0–25 °C, 0.5–12 h. Monitor by TLC/HPLC–UV (visible band). Typical yields: 50–90% depending on sterics/electronics.
• Reduction to hydroquinone: Na2S2O4 (2–5 eq) or ascorbic acid in MeOH/H2O or acetone/H2O at 0–25 °C, 0.25–2 h, under nitrogen. Alternatively, NaBH4 (1–2 eq) in MeOH at 0–5 °C with careful quench. Protect from air to prevent reoxidation.
• Diels–Alder reactions: Quinone (1.0 eq) with electron-rich dienes in toluene or chlorobenzene, 60–110 °C, 2–24 h; Lewis acids (e.g., BF3·OEt2) may accelerate. Adducts often rearomatize or undergo further redox steps.
• Cross-coupling (if aryl halides present on the scaffold): Pd-catalyzed Suzuki–Miyaura (Pd(PPh3)4 1–5 mol%, base K2CO3, solvent dioxane/H2O, 60–90 °C) or Buchwald–Hartwig amination (Pd2(dba)3/BINAP-type ligands, NaOtBu, toluene, 80–110 °C). Applicability depends on substitution pattern.
• Electrosynthesis/oxidation: Phenol-to-quinone oxidations with controlled potential (glassy carbon anode) in MeOH/MeCN with supporting electrolyte (nBu4NBF4), ambient temperature; useful for generating or regenerating quinones.

Ensure inert atmosphere and subdued light where stability is a concern. Consult the CoA/SDS for the specific material’s compatibility.

Safety and Handling

Authoritative source

• For definitive hazard classification and response measures, consult the product SDS.

Item-specific hazard fields

• GHS Classification: Not specified for this item; refer to SDS.
• Signal Word: Not specified for this item; refer to SDS.
• H-Statements: Not specified for this item; refer to SDS.
• Pictograms: Not specified for this item; refer to SDS.

General safety considerations for quinone-containing, hydrophobic small molecules (literature-informed; not product-specific)

• Potential hazards: Quinones are electrophilic and redox-active; they may be skin/eye irritants and can cause respiratory irritation if dusts/aerosols are generated. Some quinones are sensitizers. Avoid inhalation and direct contact.
• PPE: Wear lab coat, safety glasses, and appropriate gloves (e.g., nitrile). Use a chemical fume hood for weighing, transfers, and solution preparation.
• Incompatibilities: Strong reducing agents (may rapidly reduce the quinone), strong nucleophiles/bases (may add to the conjugated carbonyls), and prolonged exposure to light/air which may degrade sensitive quinonoid systems. Store away from oxidizable organics if packaged as an oxidant.
• First aid overview: Eye/skin contact—rinse with water for at least 15 minutes; remove contaminated clothing. Inhalation—move to fresh air. Ingestion—rinse mouth; seek medical attention. Always follow institutional SOPs and SDS guidance.
• Spill/cleanup: Avoid dust; scoop or adsorb with inert material. Dispose of waste according to local regulations, segregating halogenated vs non-halogenated organics as appropriate.

This product is designated for research use only.

Solvent Selection

Polarity and miscibility (general for hydrophobic quinonoid cannabinoids)

• Expected polarity: Moderately nonpolar aromatic with a polarizable quinone motif; overall hydrophobic with negligible aqueous solubility (literature, class-based).
• Common stock solvents: DMSO and acetonitrile are frequently used for analytical and screening stocks due to solubility and stability. Alcohols (EtOH, iPrOH) and chlorinated solvents (DCM, CHCl3) are also used for synthetic work.

Selection tips (general, not product specs)

• Bioassay stocks: Prepare concentrated stocks in dry DMSO (e.g., 10–50 mM), aliquot, store at −20 °C to limit freeze–thaw and oxidation. Dilute into media/buffers immediately before use with vigorous mixing to prevent precipitation; include co-solvent (≤0.1–0.5% DMSO) and carrier protein if needed for dispersion.
• Synthesis/processing: For reactions, choose aprotic solvents (DCM, toluene, MeCN) to control nucleophilic addition to the quinone. For reductions or additions, protic alcohols can be used deliberately.

Comparison (general considerations)

• DMSO: Highest solvency, convenient for screening, but can participate in redox chemistry with strong activators; minimize strong base.
• MeCN: Good solvency and low viscosity; UV-transparent, HPLC-friendly.
• DCM/CHCl3: Excellent solubility, easy workup; handle with care regarding toxicity and environmental footprint.
• EtOH/iPrOH: Greener, but lower solubility; may affect redox equilibria.

Confirm actual solubility/stability for SKU T1442253 from the CoA before scale-up.

Storage and Reconstitution

Item-specific instructions (from Product Data)

• Storage Conditions: Store at −20 °C.
• Shipped In: Ice chest + Ice pads.

General stability and handling guidance for quinone-bearing small molecules (not product-specific)

• Protect from light: Store in amber vials or wrap in foil to minimize photodegradation of the quinonoid chromophore.
• Minimize oxygen and moisture: Keep tightly capped; consider storing under inert atmosphere (N2/Ar) with desiccant. Open vials only briefly.
• Aliquoting: Prepare single-use aliquots of solids or concentrated solutions to avoid repeated freeze–thaw and headspace oxygen exposure.
• Reconstitution: If supplied as a solid, bring to room temperature in a desiccator before opening. Dissolve in a dry, oxygen-poor solvent (e.g., anhydrous DMSO or MeCN) to prepare stock solutions. Record concentration gravimetrically or by quantitative NMR where precision is required.
• Working solutions: Prepare immediately before use; avoid extended storage of diluted aqueous mixtures due to potential hydrolysis/redox changes.

These recommendations complement the item’s −20 °C storage condition. For exact stability limits, solution shelf life, and container compatibility for SKU T1442253, consult the CoA/Spec Sheet and SDS.

Structure and Identity

Item-specific identifiers (from Product Data)

• SKU: T1442253
• Product Name: Δ9-THCQ
• CAS: 860480-30-4
• Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• InChIKey: Not specified for this item; refer to CoA/Spec Sheet.

Literature identity notes (general, for context only)

• The shorthand “Δ9-THCQ” is commonly used in the literature to denote a quinone derivative of Δ9-tetrahydrocannabinol (Δ9-THC), often described as a cannabinochromene/benzoquinone-like oxidation product of the resorcinol ring of cannabinoids (cannabinoid quinone).
• Typical structural features reported in the literature for cannabinoid quinones include: an aromatic bicyclic/terpenophenolic cannabinoid core and a para- or ortho-quinone motif (two conjugated carbonyls) capable of redox cycling and Michael-type reactivity. Stereochemistry at the terpene moiety can mirror that of Δ9-THC (chiral centers retained), though exact configuration for this catalog item is not specified.

2D structural description (general, literature-based)

• Expected functional groups: conjugated quinone carbonyls (electrophilic), aryl C=C bonds, and an isoprenyl/terpenoid side chain. The quinone ring is planar and strongly electron-withdrawing, activating the ring toward nucleophilic addition and enabling reversible redox chemistry. Note: The exact substitution pattern and stereochemistry for SKU T1442253 are not specified in the Product Data and should be confirmed from the CoA/SDS.

Synthetic Utility

Functional group leverage (general for quinone-bearing cannabinoids)

• Electrophilicity: The conjugated diketone of a quinone serves as a soft electrophile toward thiols, amines, enolates, and organocuprates, enabling late-stage diversification via 1,4-addition.
• Redox toggling: Interconversion between quinone and hydroquinone allows access to masked diols or redox-switchable handles for protecting-group-like behavior.
• Conjugation handle: The chromophoric ring allows for photo/redox catalysis participation (e.g., SET processes) and facilitates monitoring by UV–vis.

Retrosynthetic value (literature-based, not item-specific)

• Quinone installation from phenols: Oxidation of resorcinol/phenolic cannabinoids (e.g., Δ9-THC derivatives) with reagents such as Ag2O, DDQ, Fremy’s salt, CAN, or electrochemical methods furnishes the corresponding quinone, suggesting routes to and from the Δ9-THCQ scaffold.
• Downstream elaborations: Michael adduct formation followed by intramolecular cyclizations, or reduction to hydroquinone followed by selective functionalization (etherification/esterification) expands chemical space around the cannabinoid core.

Analytical utility

• The pronounced carbonyl stretches (~1660–1685 cm−1) and 13C NMR signals (~180–190 ppm) of quinones support rapid structure confirmation. LC–MS readily detects adduct formation, aiding SAR campaigns.

This section outlines general synthetic logic typical for quinone-containing small molecules. Confirm compatibility with the precise structure of SKU T1442253 via its CoA/SDS.

Target Specificity

No target, antigen, or biological specificity data are provided for SKU T1442253. This product is a small-molecule research chemical, not an antibody or affinity reagent.

• Target name/epitope: Not specified for this item; refer to CoA/Spec Sheet.
• Species reactivity, clone, isotype: Not applicable.

If you intend to use this compound as a probe, empirical determination of binding/labeling selectivity is required (e.g., thermal shift assays, SPR, chemoproteomics), but no such data are provided here.