Epigomisin O - ≥98% , CAS No.73036-31-4

CAS: 73036-31-4 Cat. No.: E1027240 PubChem CID: 5317081

GRADE & PURITY ≥98%

Storage

Room temperature

Specifications

Especificações e pureza

≥98%

Condições de armazenamento de armazenamento

Room temperature

Pureza

≥98%

Nomes e identificadores

• Sorrisos canónicos: CC1CC2=CC3=C(C(=C2C4=C(C(=C(C=C4C(C1C)O)OC)OC)OC)OC)OCO3
• IUPAC Name: (8S,9S,10S)-3,4,5,19-tetramethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.02,7.014,18]nonadeca-1(19),2,4,6,12,14(18)-hexaen-8-ol
• InChIKey: GWDFJIBHVSYXQL-ZKTNFTSUSA-N
• INCHI: 1S/C23H28O7/c1-11-7-13-8-16-21(30-10-29-16)22(27-5)17(13)18-14(19(24)12(11)2)9-15(25-3)20(26-4)23(18)28-6/h8-9,11-12,19,24H,7,10H2,1-6H3/t11-,12-,19-/m0/s1
• SMILES isoméricas: C[C@H]1CC2=CC3=C(C(=C2C4=C(C(=C(C=C4[C@H]([C@H]1C)O)OC)OC)OC)OC)OCO3
• CAS alternativo: 73036-31-4
• PubChem CID: 5317081

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Classe Tannins
      • Subclass Hydrolyzable tannins

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Classe: Tannins
• Subclass: Hydrolyzable tannins
• Intermediate Tree Nodes: Not available
• Direct Parent: Hydrolyzable tannins
• Alternative Parents: Dibenzocyclooctadiene lignans Benzodioxoles Anisoles Alkyl aryl ethers Secondary alcohols Oxacyclic compounds Acetals Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Hydrolyzable tannin - Dibenzocyclooctane lignan - Benzodioxole - Anisole - Alkyl aryl ether - Benzenoid - Secondary alcohol - Acetal - Oxacycle - Organoheterocyclic compound - Ether - Alcohol - Organic oxygen compound - Hydrocarbon derivative - Organooxygen compound - Aromatic heteropolycyclic compound
• Descrição: This compound belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit.
• 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

Propriedades químicas e físicas

• Peso molecular: 416.500 g/mol
• XLogP3: 4.000
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 416.184 Da
• Monoisotopic Mass: 416.184 Da
• Topological Polar Surface Area: 75.600 Ų
• Heavy Atom Count: 30
• Formal Charge: 0
• Complexity: 574.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 3
• 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 supplier-validated application protocols are provided for this item. General guidance for small-molecule handling in research settings:

• Preparing DMSO stocks: Weigh accurately on an analytical balance; dissolve to 10–50 mM in anhydrous DMSO; vortex and sonicate if necessary. Record exact concentration based on molecular weight (obtain from CoA) and purity correction where applicable.
• Dilution into assays: Add stock to buffered media to achieve the desired final concentration, keeping DMSO ≤0.1–1% v/v unless your system tolerates more. Mix thoroughly to avoid local supersaturation.
• QC prior to use: Verify identity/purity by LC–MS or HPLC-UV. For quantitative work, confirm concentration by UV with an extinction coefficient determined empirically or by qNMR.
• Plate handling: For high-throughput screening, pre-dispense DMSO stocks into assay plates under low humidity; seal and store cold and dark to limit evaporation and degradation. Equilibrate to room temperature before unsealing to prevent condensation.

For any specialized protocols (e.g., binding assays, computational docking benchmarks), adapt standard operating procedures used for lipophilic aromatic ligands and document co-solvent percentages and incubation times.

Biological Roles

Scope: Non-clinical, biochemical context. No medical or therapeutic claims are made.

Literature/general knowledge about class and source:

• Epigomisin O belongs to the dibenzocyclooctadiene lignans, a family of secondary metabolites notably found in Schisandra species. These lignans are biosynthesized from phenylpropanoid precursors, undergoing oxidative coupling and ring closure to yield the characteristic biaryl/medium-ring framework.
• Functional chemical motifs (methoxy/aryl ether substituents) impart lipophilicity and membrane affinity, often resulting in strong interactions with hydrophobic protein pockets and lipid bilayers in biophysical assays.
• In enzymology and binding studies, lignans from this class are frequently used as tool compounds to probe: aromatic–aromatic stacking, hydrogen-bond acceptor capacity of anisole oxygens, and conformational restriction imposed by medium-sized rings.

Applications in research settings:

• Reference standard: supports dereplication and metabolite annotation in plant metabolomics and natural-products chemistry.
• Biophysical assays: utilized to characterize noncovalent interactions with proteins or membranes (e.g., fluorescence quenching, ITC), and to benchmark computational docking for polyaryl, conformationally flexible ligands.

Notes:

• Exact biological activity profiles are compound- and stereochemistry-dependent within this class. For rigorous interpretation, pair binding/assay data with unambiguous structural verification (NMR, CD, and chiroptical data) of the same batch used in experiments.

Buffer Applications

Not typically applicable. Epigomisin O is a neutral, lipophilic small molecule and does not serve as a buffering agent. For experimental use in buffered systems, prepare concentrated stocks in DMSO or ethanol and dilute into the chosen buffer with attention to final co-solvent percentages and solubility limits. Co-solvent levels of 0.1–1% DMSO are common in biochemical assays; verify tolerance for your assay system.

Green Alternatives

Context: As a defined small-molecule library member, Epigomisin O itself is not a process solvent or commodity reagent; “green alternatives” considerations mainly relate to its handling (extraction, purification, and solution preparation) rather than substitution of the molecule.

Greener handling strategies (general guidance):

• Prefer bio-based, low-toxicity solvents for solution prep where feasible: ethanol or ethyl acetate in place of chlorinated solvents for chromatography or sample dissolution (subject to solubility constraints).
• Use micro-scale workflows (analytical SFC, UHPLC) to minimize solvent consumption in method development and QC.
• For preparative isolation of lignans from natural sources, opt for aqueous ethanol as an extraction medium and implement solid-phase or membrane separations to reduce solvent-intensive steps.

Comparison of common solvent choices (general; not item-specific):

• DMSO: excellent solubilizer for assay stocks; not particularly green but used at low volumes; high boiling point complicates removal.
• Ethanol (bio-based): greener, miscible with water; moderate solubility for lipophilic lignans; good for preparative work when high concentration is not required.
• 2-MeTHF: greener ether alternative to THF/DCM for partitioning; variable solubility for bulky aromatics; good phase separation and lower peroxide tendency vs diethyl ether.

Operational notes:

• Implement solvent recycling where possible and document E-factor reductions.
• Choose silica-free or reduced-silica chromatographic methods (e.g., SFC) to curtail solvent and adsorbent waste.

Pharmaceutical Uses

No formulation grade or pharmacopeial status is provided for this item.

• Status: Research use only (per Product Data). Not for human or veterinary use.

General, non-clinical context:

• Reference/analytical standard: may be used to establish chromatographic retention times, mass spectral fingerprints, and impurity profiles for Schisandra-derived materials or synthetic lignan analogs.
• Excipients/processing: Not applicable; Epigomisin O is an active small molecule scaffold rather than an excipient. No compendial monograph is indicated.

Practical considerations for R&D formulation studies (informational only):

• Solubilization: Use DMSO or ethanol for pre-formulation screening; evaluate mixed solvent systems or cyclodextrin inclusion complexes if aqueous test systems are required.
• Stability-indicating methods: Develop LC–UV or LC–MS methods able to resolve potential oxidative or O-demethylation degradants.

Item-specific regulatory or GMP applicability: Not specified for this item; refer to CoA/Spec Sheet if GMP or traceability documentation is required.

Physical Properties

Item-specific (from Product Data):

• Molecular Formula: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.
• Appearance: Not specified for this item; refer to CoA/Spec Sheet.

Storage/Logistics:

• Storage Conditions: Room temperature (per Product Data).

Literature/general expectations for Schisandra-type dibenzocyclooctadiene lignans (not item specifications):

• Physical state: typically solids (amorphous or microcrystalline) with high aromatic content.
• Solubility profile: sparingly soluble in water; soluble in polar aprotic organic solvents (DMSO, DMF) and moderately in alcohols (MeOH, EtOH) and chlorinated solvents (DCM, CHCl3). For biological assays, DMSO stock solutions (10–50 mM) are commonly prepared.
• LogP: members of this class are lipophilic (often logP > 3, literature), reflecting multiple aryl rings and methoxy groups.
• UV–Vis: aromatic chromophores afford UV absorbance in the 200–300 nm region; exact maxima depend on substitution (use reference spectra for quantitation).
• Melting point and other constants: Not specified for this item; refer to CoA/Spec Sheet. When needed, verify by DSC or capillary MP using a dry sample.

Practical notes:

• Prior to weighing for microgram-scale assays, allow any solvent-wet material to equilibrate to ambient conditions in a desiccated environment to ensure accurate mass.
• Assess solubility in intended assay medium; co-solvent or surfactant may be required for aqueous systems.

Quality and Grades

Item-specific quality information (grade/purity) is not provided in the Product Data for SKU E1027240.

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

Guidance on interpretation (general):

• For small-molecule library members and natural-product standards, suppliers typically control identity by high-resolution MS and NMR, and purity by HPLC/UPLC-UV and/or qNMR. Chromatographic purity thresholds commonly fall in the ≥95% range for screening; analytical standards may be offered at ≥98% purity with tightly defined residual solvent limits.
• UV absorbance background: for LC/UV applications, low baseline drift and absence of co-eluting aromatic impurities are critical; consult the CoA chromatogram.
• Residual solvents/water/metals/peroxides: Not specified for this item; refer to CoA/Spec Sheet.
• Stabilizers: None stated. Where present in other items, stabilizers (e.g., BHT) can affect bioassays and analytical baselines; absence/presence should be verified on the CoA.

Recommendations:

• Request the current batch CoA for exact purity, analytical methods, and acceptance criteria.
• If using as a quantitative reference, verify purity by orthogonal methods (e.g., qNMR vs HPLC area%) and apply purity correction factors to gravimetric preparations.

Reaction and Applications

This product is sold as a research-grade small molecule/compound library member, not primarily as a synthetic reagent. Accordingly, it is most commonly used in:

• Analytical reference and profiling: LC–MS retention indexing, metabolomics/natural products dereplication, and as a reference standard for Schisandra-type lignans.
• Screening: biochemical or biophysical assays probing ligand–protein interactions, membrane partitioning, or redox properties in discovery research (no medical/clinical claims).
• Cheminformatics/medchem: scaffold similarity comparisons within dibenzocyclooctadiene lignans to guide SAR hypotheses.

If derivatization is desired (general synthetic context):

• Phenyl ethers/methoxy groups can be demethylated (e.g., BBr3) to phenols, enabling further diversification (acylation, alkylation, carbonate/urethane formation).
• Benzylic positions in related lignans can undergo selective oxidation/reduction; however, the medium-ring biaryl framework can be sensitive to harsh conditions.
• Cross-coupling on heavily substituted aromatic rings is typically challenging; electrophilic aromatic substitution is attenuated by methoxy deactivation patterns and sterics.

Practical considerations:

• Maintain anhydrous, oxygen-minimized conditions for moisture- or air-sensitive transformations on lignan derivatives if attempted.
• For analytical uses, prepare fresh solutions to minimize slow oxidative discoloration common to polyaryl ethers.

Note: No manufacturer applications were provided beyond “research use only”; the above reflects general laboratory practices for analogous lignans and should be adapted to your workflow.

Reaction Conditions

This product is not primarily supplied for use as a reagent, and no manufacturer-recommended reaction conditions are provided.

General guidance if derivatization of lignan scaffolds is attempted (literature-based, not item-specific):

• O-Demethylation to phenols: BBr3 (1–3 equiv per methoxy) in DCM at −78 to 0 °C, then warm to RT; quench with methanol/water. Workup under inert atmosphere to avoid oxidation. Yields vary depending on substitution/sterics.
• Phenol protection/derivatization: phenol → carbonate (e.g., triphosgene/DMAP) or aryl/alkyl ethers (NaH/alkyl halide) in DMF; monitor for over-alkylation.
• Benzylic oxidations (substrate dependent): TEMPO/bleach or Dess–Martin periodinane in DCM for mild oxidation; avoid strong acids/bases that may cleave aryl–oxygen bonds or perturb the medium ring.

Analytical/assay preparations:

• Stock solutions: dissolve in anhydrous DMSO (10–50 mM), vortex/sonicate; sterile-filter if needed for biological assays.
• Stability checks: assess by LC–MS after 24–72 h at ambient and refrigerated conditions to confirm solution stability.

Always adapt conditions to small-scale trials and confirm identity/purity by NMR and LC–MS after any chemical manipulation.

Safety and Handling

Authoritative safety information must be taken from the product SDS.

Item-specific hazard details (from Product Data):

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

General laboratory handling guidance for non-volatile, lipophilic natural-product lignans (informational, not a substitute for SDS):

• PPE: wear lab coat, safety glasses, and appropriate chemically resistant gloves (e.g., nitrile). Avoid inhalation of dust/particulates and contact with skin/eyes.
• Engineering controls: handle powders in a fume hood or ventilated enclosure; avoid aerosolization when preparing DMSO stocks.
• Incompatibilities: strong oxidizers may degrade phenyl ether/methoxy groups; strong acids/bases may cause hydrolysis or demethylation under forcing conditions. Store away from oxidants and moisture.
• First aid (overview): in case of skin/eye contact, rinse with water for at least 15 minutes; if inhaled, move to fresh air; if ingested, rinse mouth. Seek medical attention according to SDS guidance.
• Fire safety: treat as combustible organic solid. Use CO2, dry chemical, or foam. Combustion may generate CO/CO2 and phenolic/anisole vapors.
• Waste: collect organic waste and contaminated disposables in appropriate containers according to institutional and local regulations.

Transport/Storage:

• Storage Conditions: Room temperature as provided; protect from light and moisture in a tightly closed container. Defer to label/SDS for any specific shipping instructions.

Solvent Selection

Relevance: Epigomisin O is a neutral, lipophilic aromatic lignan. Solvent choice determines workable concentrations and assay compatibility.

General solubility guidance (literature/experience for Schisandra-type lignans; not item specifications):

• Strong solvents for stock solutions: DMSO (preferred), DMF, NMP. Typical stock: 10–50 mM in DMSO for HTS or cell-free assays.
• Moderately effective: methanol, ethanol, isopropanol, acetone, ethyl acetate, dichloromethane, chloroform. Achievable concentrations vary (often 1–10 mg/mL); verify experimentally.
• Poor: water and aqueous buffers without co-solvent/surfactant; consider ≤1–2% DMSO cosolvent, or complexation with cyclodextrins for aqueous work.

Polarity considerations:

• Expected to have high aromaticity and multiple methoxy/benzylic ether substituents ⇒ high logP and limited hydrogen bonding capacity; favors polar aprotic or moderately polar organic solvents.

When to choose alternatives:

• If chromatographic detection at low UV is essential, acetonitrile/water mobile phases with small DMSO spikes can help dissolve samples without excessive background.
• For green chemistry or scale-up isolation, ethanol or 2-MeTHF may substitute for chlorinated solvents, albeit with solubility tradeoffs.

Practical tips:

• Warm gently (≤40 °C) and sonicate to aid dissolution; avoid prolonged heating of solutions.
• Filter 0.2 µm prior to HPLC/LC–MS to remove particulates.
• Record exact solvent composition in assay notebooks to enable reproducibility.

Storage and Reconstitution

Item-specific storage from Product Data:

• Storage Conditions: Room temperature.

Additional best practices (general guidance for small, hydrophobic natural products):

• Container: Store in a tightly closed, light-protective vial with a desiccant or in a dry cabinet to minimize moisture exposure and oxidative discoloration.
• Inert atmosphere: If long-term storage is anticipated, consider purging headspace with nitrogen/argon and minimizing free headspace.

Reconstitution guidance:

• Primary solvent: DMSO is recommended for concentrated stocks due to high solvating power for lignans. Alternative solvents include DMF or ethanol, subject to assay compatibility.
• Procedure: Allow vial to equilibrate to room temperature before opening. Accurately weigh the solid (or use supplier-provided mass). Add calculated volume of solvent to reach target concentration (e.g., 10–50 mM), vortex and sonicate gently to fully dissolve. Filter (0.2 µm PTFE) if a clear solution is required.
• Aliquoting: Prepare single-use aliquots to avoid repeated freeze–thaw or prolonged bench exposure. Store aliquots at 2–8 °C or −20 °C protected from light when feasible; document stability empirically by LC–MS.

Stability specifics (water content, peroxide limits, UV cutoff, exact shelf life): Not specified for this item; refer to CoA/Spec Sheet.

Research Use Note: For research use only.

Structure and Identity

Short description: Epigomisin O is a small-molecule natural-product lignan often classified within the dibenzocyclooctadiene family (Schisandra-type lignans). It is supplied as part of a small-molecule/compound library for research use.

Item-specific identifiers (from Product Data):

• CAS: 73036-31-4
• CID (PubChem): 5317081
• InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.

Computed/literature structural context (general knowledge, not item specifications):

• Structural class: dibenzocyclooctadiene-type lignan bearing multiple aryl methoxy/oxy substituents; “epi-” indicates an alternative stereochemical configuration relative to gomisin O.
• Core features: two biaryl aromatic rings connected via an 8‑membered carbocyclic ring; typically features benzylic oxygen substituents (e.g., methoxy/benzodioxole motifs in related gomisin congeners). Stereochemistry at the cyclooctadiene ring defines the “epi” relationship.
• 2D description: two substituted phenyl rings (often 1,2,3-trimethoxy-like patterns in this class) joined through a flexible medium ring; absence of strongly ionizable groups implies neutral character under physiological pH.

Notes:

• Exact molecular formula and molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
• If precise stereochemistry, SMILES, or InChIKey are required for cheminformatics, consult the CoA/Spec Sheet or primary literature for Epigomisin O (CAS 73036-31-4).

Synthetic Utility

Primary use: a defined small molecule for screening and reference; not commonly employed as a building block. Nevertheless, the scaffold offers handles for diversification in a medicinal or natural-products chemistry context (general guidance):

Functional group reactivity typical for dibenzocyclooctadiene lignans:

• Aryl methyl ethers (–OCH3): susceptible to demethylation (BBr3, BCl3, AlCl3/thiols) to yield phenols, which can be further functionalized (alkylation, acylation, carbonate formation).
• Benzylic positions: amenable in related systems to selective oxidation (e.g., to benzylic alcohols/ketones) or reduction; caution due to possible ring rearrangement under harsh conditions.
• Aryl C–H: heavily substituted rings and conformational constraints often suppress electrophilic substitution; directed metalation may be challenging.

Utility in retrosynthesis and SAR:

• Provides a rigid, lipophilic, conformationally restricted core useful for probing hydrophobic binding pockets.
• Phenolic derivatives (post-demethylation) can be leveraged for prodrug or conjugation strategies (e.g., carbonate linkers for affinity probes).

Analytical utility:

• Serves as a calibration or system-suitability compound for methods aimed at complex polyaryl ether natural products (evaluate retention, ionization efficiency in ESI/APCI).

Note: No item-specific reactivity specifications are provided; the above reflects literature behavior of analogous lignans.

Target Specificity

Not applicable. This product is a small-molecule natural product and is not an antibody, protein, or nucleic acid with defined biological targets in the supplier’s documentation. Any target engagement studies should be treated as exploratory and validated independently under your assay conditions.