This compound belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.
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
330.300 g/mol
XLogP3
2.100
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
6
Rotatable Bond Count
5
Exact Mass
330.11 Da
Monoisotopic Mass
330.11 Da
Topological Polar Surface Area
93.100 Ų
Heavy Atom Count
24
Formal Charge
0
Complexity
422.000
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
Calcolatori di soluzioni
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Recensioni
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Application Protocols
Item-specific tested applications are not provided for this listing. The following are general, literature-inspired procedures to help design experiments. Adjust to your system and consult primary sources.
A. Preparation of stock solutions
Weigh compound quickly to minimize moisture uptake. Dissolve in anhydrous DMSO to 10–100 mM. Vortex and, if needed, sonicate briefly. Aliquot into amber vials (10–50 μL) and store at −20 °C. Avoid repeated freeze–thaw; use single-use aliquots.
B. Cell-based ROS assay (DCFH-DA) workflow (general)
Seed cells to reach 70–90% confluence on assay day.
Load with DCFH-DA per probe instructions; wash to remove excess.
Treat with diapocynin at a range of concentrations (e.g., 1–50 μM final; keep DMSO ≤0.1–0.2% v/v). Include vehicle control and a known ROS modulator as assay control.
Stimulate ROS production (e.g., PMA for NOX2 systems) as appropriate. Record fluorescence kinetics, correcting for background and any compound autofluorescence.
C. Enzymatic generation/verification (HRP/H2O2 coupling)
In phosphate buffer (pH ~7) with 10–30% ethanol, mix apocynin and catalytic HRP. Add H2O2 dropwise while stirring at RT. Monitor by HPLC; upon completion, quench residual peroxide with catalase or sodium sulfite. Isolate diapocynin by extraction and crystallization.
Quality controls
Verify solution clarity after dilution into media. Use LC–MS to confirm absence of residual monomer/apocynin if this could confound results.
Biological Roles
Scope: The following summarizes literature-reported biological roles of diapocynin as a research chemical. It is not a therapeutic claim and is provided solely to guide experimental design.
Literature/general findings
NADPH oxidase pathway research: Diapocynin is widely used to interrogate NOX-dependent ROS production in cells and isolated systems. Studies often report attenuation of superoxide or hydrogen peroxide signals attributed to interference with assembly/activation of NOX complexes derived from apocynin-like chemistry.
Antioxidant/phenoxyl radical chemistry: The phenolic biphenyl core can participate in radical scavenging and redox buffering in model systems, influencing ROS readouts and oxidative modifications of biomolecules.
Cell signaling context: By modulating ROS, diapocynin may affect redox-sensitive pathways (e.g., NF-κB, MAPK) in cell-based experiments. Effects are cell-type and condition dependent, and off-target redox interactions are possible.
Experimental considerations
Verify target engagement with orthogonal assays (e.g., inhibitor-insensitive controls, genetic knockdown/knockout of NOX components) to distinguish direct NOX pathway effects from general antioxidant behavior.
Control for solvent and intrinsic absorbance/fluorescence that may interfere with probe-based ROS assays.
Report exact lot, solvent, and working concentration since phenolic compounds can display assay-dependent behavior.
Buffer Applications
This compound is not a buffering agent and is not typically used to formulate pH buffer systems.
Practical notes for use in buffered systems (general)
If adding to aqueous buffers (e.g., PBS, HBSS), dissolve first in a miscible organic cosolvent such as DMSO or ethanol to create a concentrated stock, then dilute with vigorous mixing.
Monitor for precipitation upon dilution; if observed, increase cosolvent fraction slightly (keeping within biological assay tolerances) or use solubilizing excipients (e.g., 2-hydroxypropyl-β-cyclodextrin).
Adjust pH only of the buffer; do not attempt to use diapocynin as a buffering component.
Green Alternatives
Context: As a solid research reagent, the green considerations for diapocynin center on how it is synthesized, dissolved, and handled rather than replacing the molecule itself.
Greener synthesis concepts (literature)
Biocatalytic oxidative coupling: Horseradish peroxidase (HRP) with H2O2 can dimerize apocynin in water/alcohol mixtures at ambient temperature, minimizing metal salt waste and chlorinated solvents.
Electrochemical oxidation: Anodic coupling of apocynin in benign solvents avoids stoichiometric oxidants and can be powered by renewable energy.
Avoid halogenated solvents: Use ethanol, methanol, ethyl acetate, or 2-MeTHF where feasible during workup and purification.
Solvent and process comparisons (general)
DMSO vs ethanol for stock solutions
DMSO: superior solubility; minimal volume needed; difficult to remove; higher EHS persistence.
Ethanol: renewable and low toxicity; may require larger volumes; easier removal and lower environmental burden.
Waste minimization
Use highly concentrated stock solutions to reduce solvent volume in assays.
Adopt microscale reactions and chromatography with greener eluents (ethyl acetate/hexanes or ethanol/water gradients).
Implement solvent recovery where possible.
Trade-offs
Biocatalytic routes can be sensitive to pH and H2O2 dosing (over-oxidation risk), while metal oxidants are robust but generate waste. Selection should balance E-factor, scalability, and required purity for the intended research use.
Pharmaceutical Uses
No pharmacopeial/excipient grade or formulation role is specified for this item; it is supplied for research use only.
General formulation context (literature/practice)
As a small-molecule research tool, diapocynin may be formulated into DMSO-based stock solutions for in vitro testing or into simple vehicle systems (e.g., PEG400/ethanol/saline) for exploratory in vivo research in academic settings. Any such use must follow institutional approvals and is outside the scope of this catalog listing.
There are no compendial monographs (USP/EP/JP) specific to diapocynin known in the public domain. Stability, impurity limits, and residual solvents must therefore be established on a per-lot basis for any regulated development work.
Best practices for research formulations
Filter sterilize solutions through 0.22 μm PTFE or PES where sterility is required.
Document solvent composition rigorously; small changes in vehicle can alter exposure and assay outcomes.
Conduct forced-degradation and short-term stability checks (light, temperature, pH) before extended studies.
Physical Properties
Item-specific specifications
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.
Literature/general physical data (for orientation only; verify against your CoA)
Physical state: typically an off-white to light tan crystalline solid (literature reports; appearance can vary with synthesis and purity).
Solubility: sparingly soluble in water; soluble in polar organic solvents (DMSO, DMF) and moderately soluble in alcohols (methanol, ethanol) — literature.
Partitioning: expected moderate lipophilicity due to biphenyl core balanced by phenol/acetyl groups (qualitative, literature rationale).
UV-Vis: aromatic phenol/anisole chromophores give strong UV absorbance in the 220–300 nm range (literature/typical for phenolic biphenyls); exact ε, λmax not specified for this item.
Melting point, boiling point, density, pKa, logP, and refractive index: Not specified for this item; refer to CoA/Spec Sheet.
Practical notes
Dissolution: prepare concentrated stocks in anhydrous DMSO (e.g., 10–100 mM), then dilute into aqueous media with vigorous mixing to avoid precipitation.
Light/air sensitivity: phenolic compounds can undergo slow oxidative changes; minimize prolonged exposure to air and light, and use amber vials where possible.
Quality and Grades
Item-specific grade/purity
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
How to interpret grade (general guidance)
Research-grade small molecules are typically qualified by NMR, LC/GC purity, and HRMS. When available, HPLC or GC purity percentages reflect the main component area under standardized conditions; they do not guarantee absence of trace impurities.
Low-residual-solvent and low-UV-absorbing grades (e.g., HPLC grade solvents) are not directly applicable to this solid; instead, look for analytical data such as 1H/13C NMR spectra, LC purity, and water content (Karl Fischer) where relevant.
Stabilizers/inhibitors
No stabilizer is specified for this item. If present in a particular lot, stabilizers will be disclosed on the CoA. Phenolic compounds generally do not require added inhibitors but benefit from dry, cool, light-protected storage.
What is specific to this item
Storage at −20 °C and cold shipment are specified, supporting stability for long-term research use. For applications sensitive to trace metals/oxidants (e.g., redox assays), consider pre-testing background reactivity and filtering solutions to remove particulates.
User checklist
Request the CoA prior to critical experiments.
Verify identity (NMR, MS) upon receipt if structure-sensitive endpoints are planned.
Record lot number and CoA version in your ELN for traceability.
Reaction and Applications
Research applications (literature/general)
Redox biology tool: Widely used as a probe/agent in studies of cellular reactive oxygen species (ROS) signaling and oxidative stress. Diapocynin originates from the oxidative coupling of apocynin and is often explored in the context of NADPH oxidase (NOX)-related pathways in cells and biochemical systems.
Chemical reactivity: The molecule contains phenolic, methoxy, and aryl ketone motifs, enabling typical phenol chemistry (etherification, acylation, metalation), carbonyl transformations (oxime/hydrazone formation), and cross-coupling after suitable activation.
Analytical/assay contexts
Employed as a reference material/positive control in ROS inhibition assays (e.g., DCFH-DA fluorescence, chemiluminescent probes) and in measuring superoxide/hydrogen peroxide production in cell or membrane preparations.
Synthetic preparation (literature)
Obtained by oxidative dimerization of apocynin using:
Peroxidase/H2O2 systems (e.g., horseradish peroxidase, HRP) in aqueous-organic media.
Single-electron oxidants (FeCl3, Ag2O, CuCl2) in alcohols or acetonitrile.
Electrochemical oxidation of apocynin in protic solvents.
Practical guidance
Purity matters: residual apocynin or quinonoid byproducts can confound redox assays; verify by HPLC and NMR.
Avoid metal contamination for redox studies; pre-rinse glassware with acid and use high-purity solvents.
For cell work, confirm lack of innate fluorescence interference at selected excitation/emission settings.
Reaction Conditions
General conditions for synthesis and derivatization (literature)
Oxidative dimerization of apocynin to diapocynin
Enzymatic route: Horseradish peroxidase (HRP, catalytic units per mmol apocynin) with H2O2 (1–2 eq added slowly) in aqueous ethanol or phosphate buffer (pH ~7) at room temperature. Reaction monitored by TLC/HPLC; typical times 0.5–4 h. Over-oxidation minimized by slow peroxide feed.
Metal-oxidant route: FeCl3 (1–2 eq) in MeOH or MeCN at 0–25 °C; reaction 0.5–2 h under air or inert atmosphere. Workup by quench with water/NaHCO3 and extract with ethyl acetate.
Electrochemical route: divided cell, Pt or glassy carbon anode, MeOH/H2O electrolyte with supporting salt (e.g., Bu4NBF4). Constant current electrolysis at ambient temperature; isolate by crystallization or chromatography.
Derivatization examples
O-alkylation: K2CO3 (2–3 eq), alkyl halide (1.2–2 eq) in acetone or DMF, 25–50 °C, 2–16 h; monitor for dialkylation.
Oxime formation: hydroxylamine hydrochloride (1.5–2 eq), pyridine or AcOH, MeOH/EtOH, reflux 2–6 h.
Reduction of aryl ketones: NaBH4 (1–2 eq) in MeOH/EtOH at 0–25 °C, 0.5–2 h; quench carefully.
Analytical checkpoints
LC–MS and 1H/13C NMR confirmation of symmetry and absence of apocynin monomer.
Yields: Literature yields vary widely (30–80%) depending on oxidant, solvent, and workup; optimize equivalents and addition rates to improve selectivity.
Safety and Handling
Item-specific safety data
GHS Classification: Not specified for this item; refer to SDS.
Pictograms: 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.
Storage Conditions: Store at −20 °C (Product Data). Shipped in ice chest + ice pads.
General laboratory safety guidance (literature/best practice; not a substitute for the SDS)
Likely hazards: Phenolic/aromatic ketone compounds are commonly classified as irritants; avoid inhalation of dust and contact with skin/eyes. Handle powders in a fume hood.
PPE: lab coat, safety glasses, and appropriate chemical-resistant gloves (e.g., nitrile). Use respiratory protection if dust cannot be controlled.
Incompatibilities: strong oxidizers or strong bases can alter phenolic/ketone functionalities; avoid prolonged exposure to strong reducing agents that may affect quinonoid tautomers. Store away from acids/bases that may catalyze degradation.
First aid overview: in case of skin contact, wash with plenty of water/soap; eye contact, rinse cautiously with water for several minutes and seek medical attention; inhalation, move to fresh air; ingestion, rinse mouth and seek medical attention. Follow institutional SOPs.
Spill/cleanup: Avoid dust formation. Sweep up solids with minimal agitation; dispose according to local regulations. For solutions, absorb on inert material.
Stability: Keep container tightly closed, desiccated, and protected from light to limit oxidative discoloration or degradation.
Always consult the product-specific SDS for authoritative hazard, toxicology, and response information.
Solvent Selection
Applicability: Diapocynin is a hydrophobic, polyfunctional aromatic solid. Solvent selection is primarily for dissolution/stock preparation and for synthetic transformations.
Aqueous media: poorly soluble; requires cosolvent (DMSO, ethanol) or cyclodextrins to achieve useful concentrations.
Organic solvents: high solubility in DMSO/DMF; moderate in methanol/ethanol; lower in acetone/ethyl acetate; limited in nonpolar hydrocarbons.
Typical use scenarios
Bioassays/cell culture: prepare concentrated DMSO stocks (e.g., 10–100 mM). Final assay DMSO content commonly kept ≤0.1–0.5% v/v to maintain cell viability; optimize per cell line.
Spectroscopy/analytics: methanol, acetonitrile, or DMSO are convenient for HPLC/UV-Vis due to strong aromatic absorbance.
Synthetic manipulation: DMF, DMSO, or acetonitrile for nucleophilic or oxidative conditions; alcohols for acylation/transesterification chemistry if derivatization is planned.
Small comparison (general)
DMSO: maximum solubilizing power; high boiling point; hygroscopic; compatible with most bioassays at low %.
Acetonitrile: good for analytics; modest solubility; volatile; less protic than alcohols.
Practical tips
Warm gently (≤40 °C) and vortex/sonicate to aid dissolution; avoid overheating to prevent degradation.
Filter solutions (0.22–0.45 μm PTFE) for cell/biochemical assays to remove particulates.
Confirm absence of precipitation after dilution into aqueous buffers; add solvent last with rapid mixing.
Storage and Reconstitution
Item-specific instructions
Storage temperature: Store at −20 °C (Product Data).
Shipping: Ice chest with ice pads (Product Data).
General best practices for this compound class
Solid stability: Keep container tightly closed in a dry, inert atmosphere if available (desiccant recommended). Protect from light to minimize oxidative changes. Allow vial to warm to room temperature in a desiccator before opening to avoid moisture condensation.
Reconstitution: Prepare concentrated stocks in anhydrous DMSO (typical 10–100 mM). For short-term aqueous work, dilute into pre-warmed buffer with vigorous mixing; use immediately to minimize precipitation.
Aliquoting: Divide stock into single-use portions (amber microtubes) to prevent freeze–thaw cycles. Store aliquots at −20 °C to −80 °C.
Shelf life (general guidance): In the absence of item-specific stability data, prepare fresh working solutions on the day of use. Assess integrity of stored stocks periodically by HPLC/LC–MS (look for new peaks, discoloration).
Adsorption/containers: Use glass or high-quality polypropylene. Rinse syringes/vials with small amounts of solvent to recover adsorbed material when working at low micromolar levels.
Unspecified parameters
Water content limits, residual solvent limits, and exact stability windows are not specified for this item; refer to the CoA/Spec Sheet and SDS for authoritative guidance.
Structure and Identity
Brief overview: Diapocynin is the oxidative dimer of apocynin (4-hydroxy-3-methoxyacetophenone), furnishing a biphenyl framework bearing phenolic, methoxy, and acyl functionalities. It is commonly used as a redox biology research tool.
Item-specific identifiers (from Product Data)
CAS: 29799-22-2
PubChem CID: 9927489
InChIKey: 124707 (as provided)
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.
Structural features (literature/general description)
Functional groups: two phenolic –OH groups, two methoxy –OCH3 substituents, and two acetyl (–COCH3) groups paratopic to the phenols in many reported structures of diapocynin formed by oxidative coupling of apocynin.
2D structure (verbal): a 1,1′-biphenyl where each ring bears one hydroxy, one methoxy, and one acyl substituent in a pattern inherited from apocynin after para–para radical coupling.
Multiple synthetic routes can yield closely related oxidative dimers; always verify exact substitution pattern for your lot via the CoA/NMR/HRMS if structure-sensitive applications are planned.
Synthetic Utility
Retrosynthetic/value perspective (general)
Diapocynin is a symmetrical, polyfunctional biphenyl that can serve as a scaffold for synthesizing libraries of redox-active phenolic derivatives. Each ring offers orthogonal handles: phenol (for O-functionalization), methoxy (for demethylation to phenols), and aryl ketone (for oxime/hydrazone formation or further elaboration).
Transformations (literature/typical)
Phenolic derivatization: selective O-alkylation/acylation under base (NaH, K2CO3) in DMF/acetone to tune polarity or block H-bonding.
Carbonyl chemistry: formation of oximes/hydrazones (NH2OH, hydrazines) in alcohols or acetic acid; reduction to secondary alcohols (NaBH4, catalytic hydrogenation) to probe structure–activity.
Cross-coupling after activation: conversion of phenols to triflates or aryl halides (via diazotization/halogenation of derived anilines or via directed ortho-metalation pathways) enables Suzuki/Negishi couplings for ring elaboration.
Demethylation: BBr3 or AlCl3/thiols can convert anisoles to catechols for further coupling or chelation studies; proceed at low temperature to preserve the ketone.
Use in materials/analytics
The conjugated biphenyl with phenolic/ketone donors can act as a ligand precursor or redox-active motif in model complexes.
Caveats
The presence of multiple activating groups can lead to overreaction or polymerization under harsh electrophilic conditions; employ protecting groups or chemoselective conditions as needed.
Target Specificity
Item-specific antigen/epitope/clone data are not applicable; this product is a small molecule, not an antibody or protein reagent.
Literature/general target context for small molecules
Reported primary research target: components of the NADPH oxidase (NOX) system, particularly processes involved in assembly/activation leading to ROS generation. Exact molecular binding targets remain a subject of study, and activity may derive from redox modulation rather than a single high-affinity site.
Isoform considerations: Effects are frequently documented in NOX2-dominant systems; outcomes can be cell-type and isoform dependent. Confirm specificity using genetic controls (e.g., gp91phox/NOX2 knockout) and orthogonal inhibitors.
Recommendation
Do not ascribe narrow target specificity without corroborating data in your system. Employ counter-screens to rule out general antioxidant or off-pathway effects.
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