Epivogeloside - ≥98% , CAS No.118627-52-4

CAS: 118627-52-4 Cat. No.: E988582 PubChem CID: 14192590

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: COC1CC2C(C(OC=C2C(=O)O1)OC3C(C(C(C(O3)CO)O)O)O)C=C
• IUPAC Name: (3S,4aS,5R,6S)-5-ethenyl-3-methoxy-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,4a,5,6-tetrahydro-3H-pyrano[3,4-c]pyran-1-one
• InChIKey: RAYZRCGMIDUTKS-RJFLBQOQSA-N
• INCHI: 1S/C17H24O10/c1-3-7-8-4-11(23-2)26-15(22)9(8)6-24-16(7)27-17-14(21)13(20)12(19)10(5-18)25-17/h3,6-8,10-14,16-21H,1,4-5H2,2H3/t7-,8+,10-,11+,12-,13+,14-,16+,17+/m1/s1
• SMILES isoméricas: CO[C@@H]1C[C@H]2[C@H]([C@@H](OC=C2C(=O)O1)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)C=C
• PubChem CID: 14192590

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Classe Organooxygen compounds
      • Subclass Carbohydrates and carbohydrate conjugates
        • Level5 Glycosyl compounds
          • Level6 O-glycosyl compounds

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Classe: Organooxygen compounds
• Subclass: Carbohydrates and carbohydrate conjugates
• Intermediate Tree Nodes: Glycosyl compounds
• Direct Parent: O-glycosyl compounds
• Alternative Parents: Hexoses Delta valerolactones Oxanes Vinylogous esters Enoate esters Secondary alcohols Polyols Oxacyclic compounds Monocarboxylic acids and derivatives Acetals Primary alcohols Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic heteropolycyclic compounds
• Substituents: Hexose monosaccharide - O-glycosyl compound - Delta valerolactone - Delta_valerolactone - Oxane - Monosaccharide - Vinylogous ester - Alpha,beta-unsaturated carboxylic ester - Enoate ester - Secondary alcohol - Carboxylic acid ester - Lactone - Oxacycle - Organoheterocyclic compound - Carboxylic acid derivative - Acetal - Polyol - Monocarboxylic acid or derivatives - Carbonyl group - Organic oxide - Alcohol - Primary alcohol - Hydrocarbon derivative - Aliphatic heteropolycyclic compound
• Descrição: This compound belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.
• 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: 388.400 g/mol
• XLogP3: -0.900
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 5
• Exact Mass: 388.137 Da
• Monoisotopic Mass: 388.137 Da
• Topological Polar Surface Area: 144.000 Ų
• Heavy Atom Count: 27
• Formal Charge: 0
• Complexity: 592.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 9
• 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

There are no item-specific validated application protocols provided for this product. The following are general, non-binding guidelines for using small molecules in research assays.

• Item-specific (Product Data):

  • Manufacturer Applications: Not specified for this item; refer to CoA/Spec Sheet.

• General protocols (not item-specific):

  • HTS/Assay setup:
    • Prepare a 10–50 mM DMSO stock. Verify solubility visually and by LC–MS.
    • Dispense into assay plates using calibrated acoustic or pin/inkjet devices. Include DMSO-only controls and known reference compounds.
    • Aim for a final DMSO concentration of ≤0.5% v/v (cellular) or ≤1% v/v (biochemical), unless assay tolerates higher.
  • Dose–response:
    • Use 8–12 point, half-log dilutions. Incubate per assay requirements and fit data with a four-parameter logistic model. Confirm Hill slope reasonableness and replicate across days.
  • Orthogonal confirmation:
    • Validate hits using an independent readout (e.g., fluorescence vs luminescence; enzymatic vs thermal shift) to rule out artifacts.
  • Storage/handling:
    • Store master stocks at recommended conditions; aliquot to minimize freeze–thaw. Track plate seal integrity and evaporation via control well performance.

• Reporting:

  • Document batch ID, solvent, concentration, and preparation date in ELN/LIMS. Attach CoA/SDS and chromatograms to records.

Biological Roles

Biological information for this specific catalog item has not been provided. Do not infer activity or function without primary data.

• Item-specific (Product Data):

  • No biological role, target, or pathway annotations are provided for this item. Research Use Note: For research use only.

• General considerations (not item-specific):

  • Small molecules in screening libraries may interact with diverse protein classes (enzymes, receptors, transporters) or modulate pathways in phenotypic assays. Any observed activity requires validation for specificity, potency, and mechanism.
  • Evaluate liabilities such as pan-assay interference (PAINS), redox cycling, covalent reactivity, aggregation, or fluorescence/absorbance that can confound readouts.
  • Establish preliminary ADME profiles (solubility, stability in buffer/serum, permeability, microsomal stability) to contextualize biological data.

• Practical guidance:

  • If activity is detected, perform dose–response in multiple assay formats, assess Hill slopes, and confirm with orthogonal detection methods.
  • Consider counter-screens against unrelated targets and evaluate cytotoxicity to distinguish specific effects from general toxicity.

• Compliance note:

  • No clinical or therapeutic claims are made or implied. This product is intended strictly for laboratory research use.

Buffer Applications

This product is a small-molecule library entry and not a buffering reagent.

• Item-specific (Product Data):

  • No buffer-related specifications or intended use as a pH buffer are provided.

• General guidance (not item-specific):

  • When preparing assay solutions containing small molecules, use established biological buffers (e.g., PBS, HEPES, Tris) suited to your target system. Maintain solvent content (e.g., DMSO) at ≤0.1–1% v/v to avoid perturbing pH or biological function.
  • Pre-dilute DMSO stocks into buffer slowly with mixing to mitigate precipitation; consider adding co-solvent (e.g., 5–10% ACN or EtOH) if compatible with the assay and necessary for solubility.
  • Filter sterilize (0.22 µm) only if the compound is stable and does not adsorb significantly to membranes; otherwise, prepare fresh solutions aseptically.

• Not applicable:

  • No buffering capacity, pKa, or Henderson–Hasselbalch formulation details can be provided for this item in the absence of structure-specific acid/base groups. Refer to CoA/Spec Sheet for any solubility or pH stability notes.

Green Alternatives

Green chemistry considerations for handling and using this small-molecule library item focus on solvent and process choices, as the compound-specific environmental profile is not provided.

• Item-specific (Product Data):

  • Hazard and environmental classifications: Not specified for this item; refer to SDS.

• Greener handling strategies (general):

  • Prefer greener solvents for dissolution, analytics, and workup where feasible. If DMSO is acceptable, it is generally considered a safer polar aprotic alternative to DMF or NMP. For chromatographic methods, consider water/ethanol or water/acetonitrile gradients instead of halogenated solvents when compatible with the compound.
  • Minimize solvent volumes in stock preparation and plate replication. Use sealed, low-dead-volume storage to reduce evaporative losses and waste.

• Comparative solvent table (general; selection depends on compound compatibility):

  • Water/EtOH: Low toxicity, renewable content; limited solvency for hydrophobic analytes.
  • DMSO: Broad solvency, good assay compatibility; high boiling point complicates removal.
  • Acetonitrile: Cleaner waste streams than many chlorinated solvents; flammable and toxic—use judiciously.
  • Ethyl acetate/2-MeTHF for workups (if ever needed): Often greener than dichloromethane.

• Waste management:

  • Consolidate organic waste streams by solvent family; avoid chlorinated solvents unless absolutely necessary.
  • Implement micro-scale assay development to reduce reagent and solvent consumption.

• Note: Without item-specific persistence, bioaccumulation, or toxicity data, default to conservative, low-impact laboratory practices.

Pharmaceutical Uses

No pharmacopeial status or excipient role is provided for this item. It is supplied strictly for research use.

• Item-specific (Product Data):

  • Research Use Note: For research use only.
  • No USP/EP/JP monograph or GMP-grade designation is indicated. Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.

• General formulation context (not item-specific):

  • If used in preclinical research, early solubility and stability assessments in biorelevant media (FaSSIF/FeSSIF, simulated gastric/intestinal fluids) can inform feasibility studies, but such uses remain research-only and outside clinical applications.
  • For in vitro assays, prepare DMSO stocks and dilute into assay buffers to minimize precipitation and nonspecific binding. Track final solvent percentage carefully.

• Caution:

  • This product is not intended for human or veterinary use, diagnostic procedures, or as an active pharmaceutical ingredient or excipient in any clinical setting.

• Documentation:

  • For any regulated work (e.g., GLP discovery studies), retain the CoA/SDS, batch traceability, and analytical confirmation data (HPLC/LC–MS, NMR) in your study files.

Physical Properties

Summary: Key physicochemical parameters for this catalog item are not specified in the provided Product Data.

• Item-specific (Product Data):

  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular Formula: Not specified for this item; refer to CoA/Spec Sheet.
  • Melting/Boiling Point: Not specified for this item; refer to CoA/Spec Sheet.
  • Density, Refractive Index: Not specified for this item; refer to CoA/Spec Sheet.
  • Aqueous/organic solubility: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/computed values (general guidance, not item-specific):

  • If Epivogeloside is a glycoside-like scaffold, such compounds often exhibit moderate to high polarity and may show better solubility in polar protic solvents (e.g., MeOH, EtOH) or DMSO; true behavior must be confirmed experimentally (general knowledge).

• Practical characterization tips (general):

  • Conduct a mini solubility screen at small scale (1–2 mg): test DMSO, MeOH, EtOH, acetonitrile, water, and PBS at room temperature. Start at 10 mg/mL in DMSO, then dilute into assay buffers to desired working concentrations while monitoring for precipitation.
  • If the substance is a solid, determine approximate melting behavior with DSC or capillary melting; for liquids, measure density and refractive index to aid identity verification.
  • Use UHPLC-UV (and LC–MS if available) to profile purity and stability in intended solvents. Record UV spectra to understand absorbance cutoffs relevant to analytical methods.

• Note: For authoritative specifications and acceptance criteria, always consult the item’s CoA/Spec Sheet.

Quality and Grades

Overview: Grade and purity descriptors are not specified in the provided Product Data for this item. The compound is listed under a small-molecule/compound library category for research use.

• Item-specific (Product Data):

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

• How to interpret grades (general guidance):

  • Research-grade library compounds typically emphasize identity confirmation (NMR/LC–MS), assay-ready purity (often ≥95% by HPLC/UPLC), and documentation of counter-ions/residual solvents. In the absence of a grade label (e.g., “analytical,” “HPLC,” or “bioactive screening”), consult the CoA for numeric purity, chromatographic method, and detection wavelength(s).
  • Low UV absorbance requirements (HPLC-grade solvents) or trace-metal specifications are relevant for chromatographic use of solvents, but are typically not defined for solid small molecules; for this item, any such limits are Not specified for this item; refer to CoA/Spec Sheet.

• Verification best practices (general):

  • Confirm identity by LC–MS and 1H NMR upon receipt, especially for screening/medicinal chemistry programs.
  • Record water content (e.g., by Karl Fischer) if hygroscopicity is suspected; note that water/peroxide/metal limits are Not specified for this item; refer to CoA/Spec Sheet.
  • For salt forms, verify counter-ion stoichiometry and report concentration on a free-base or free-acid equivalent basis as appropriate.

Reaction and Applications

Use context: This product is listed in a small-molecule/compound library category and is primarily intended for research screening and discovery workflows rather than as a general synthetic reagent.

• Item-specific (Product Data):

  • Manufacturer Applications: Not specified beyond category placement; refer to CoA/Spec Sheet.

• General research applications (not item-specific):

  • High-throughput screening (HTS) and fragment/add-on libraries for target validation and hit identification.
  • Phenotypic assays in cells or organisms where broad chemical diversity is desired.
  • Chemical biology probes for pathway interrogation once activity is independently validated.

• Practical tips:

  • Maintain a master DMSO stock with aliquots to minimize freeze–thaw and evaporation-induced concentration drift.
  • Track plate maps and barcodes rigorously; include inter-plate controls (positive and negative) for HTS.
  • For mechanistic studies (if an activity is observed), deploy orthogonal assays (e.g., biochemical vs biophysical such as DSF, MST, ITC) to confirm direct interaction and avoid assay interference.

• Synthetic chemistry note:

  • Without known functional groups, this item is not recommended as a building block. If a structure becomes available, map potential transformations (e.g., glycoside hydrolysis, acylation, oxidation/reduction) accordingly—but do not assume applicability without verified structure and stability data.

Reaction Conditions

No item-specific reaction conditions are applicable because this product is provided as a small-molecule library member with unspecified functional groups.

• Item-specific (Product Data):

  • No recommended synthetic reactions or process conditions are provided.

• General guidance for handling in solution (not item-specific):

  • Stock preparation: Dissolve in dry DMSO at 10–50 mM as solubility permits. If needed, warm gently (≤40 °C) and sonicate briefly. Avoid prolonged heating without stability data.
  • Dilution into assay media: Add stock slowly into vigorously mixed buffer to minimize local supersaturation and precipitation. Maintain final organic solvent content as low as assay allows.
  • Stability checks: Use LC–MS or HPLC to evaluate solution stability over 24–72 h at room temperature or 4 °C. Assess light sensitivity with foil-wrapped controls.

• If synthetic transformations are contemplated (only after structure confirmation):

  • Choose solvent and temperature regimes guided by functional group tolerance (e.g., protect labile glycosidic linkages from strong acids/bases; avoid high-temperature conditions that may cause hydrolysis or rearrangement). These are general considerations and not recommendations for this specific item.

• Reminder: For any reaction planning, obtain the complete structural and stability dossier from the CoA/Spec Sheet and SDS.

Safety and Handling

Safety summary: Limited hazard information has been provided for this product entry. Handle as a laboratory chemical of unknown hazards.

• Item-specific (Product Data):

  • GHS Classification: Not specified for this item; refer to SDS.
  • Signal Word: Not specified for this item; refer to SDS.
  • H-Statements/Pictograms: Not specified for this item; refer to SDS.
  • Storage Conditions: Room temperature (per product data).

• General laboratory precautions (not item-specific; follow SDS/CoA):

  • PPE: Lab coat, safety glasses, and appropriate chemically resistant gloves. Use in a fume hood to minimize inhalation exposure, especially during weighing and solution preparation.
  • Hygiene: Avoid ingestion, inhalation of dust/aerosols, and skin/eye contact. Wash hands thoroughly after handling. Do not pipette by mouth.
  • First aid (general): If inhaled, move to fresh air; for skin contact, wash with soap and water; for eye contact, rinse cautiously with water for several minutes and seek medical attention; if ingested, rinse mouth and seek medical advice. Provide the SDS to medical personnel.

• Handling/stability considerations (general):

  • Protect from extreme temperatures, moisture, and light until specific stability data are known. Use clean, dry tools to avoid cross-contamination.
  • If preparing concentrated DMSO or alcohol stocks, label containers with solvent, concentration, and preparation date. Assess stability by periodic LC–MS or HPLC checks.

• Disposal: Dispose of unused material and solutions in accordance with institutional chemical waste procedures and local regulations.

• Definitive safety information: Always defer to the product SDS for authoritative hazard classification and response measures.

Solvent Selection

With no item-specific solubility data provided, select solvents empirically while prioritizing analytical compatibility and assay requirements.

• Item-specific (Product Data):

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

• General solvent strategy (not item-specific):

  • Stock solutions for screening: DMSO is the default for small-molecule libraries due to broad solvating power and biological assay compatibility at ≤1% v/v. Prepare 10–50 mM stocks as solubility allows.
  • Polar protic options: Methanol or ethanol may be suitable for compounds with hydrogen-bonding capacity; they can be co-solvents for aqueous dilutions.
  • Aqueous media: If the compound is ionizable, buffered saline (pH 6–8) may work, but verify stability and avoid high pH unless supported by stability data.
  • Aprotic organics: Acetonitrile and DMF can aid solubility but consider cytotoxicity and protein denaturation in bioassays; keep final assay solvent content low.

• Practical workflow:

  • Perform a solubility screen at room temperature: DMSO → MeOH → ACN → water/PBS. Start with 1–2 mg in 100–200 µL; sonicate briefly and inspect for clarity.
  • For LC–MS analytics, prefer ACN/water with 0.1% formic acid (positive mode) or 5–10 mM ammonium acetate (negative mode), adjusting to avoid compound degradation.

• Comparative notes (general):

  • DMSO vs DMF: DMSO is more assay-compatible; DMF may be reserved for stubborn solutes.
  • MeOH vs EtOH: MeOH offers stronger solvency; EtOH is gentler for cells but often less powerful.

Storage and Reconstitution

Storage and solution preparation guidance for this catalog item are summarized below.

• Item-specific (Product Data):

  • Storage Conditions: 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.

• General storage guidance (not item-specific):

  • Keep container tightly closed in a dry, well-ventilated place away from direct light and heat sources. If hygroscopic or light-sensitive behavior is suspected, consider desiccation and amber glass.
  • For long-term retention of screening integrity, many labs store DMSO stocks at −20 °C to slow degradation; equilibrate to room temperature before opening to prevent moisture ingress. Validate that such storage is compatible with this item’s stability once data are available.

• Reconstitution (general approach):

  • Prepare a concentrated DMSO stock (e.g., 10–50 mM) if soluble. If aqueous solubility is required, test co-solvent strategies (stepwise dilution from DMSO into buffer) and monitor for precipitation.
  • Filter sterilization (0.22 µm) is optional and only if the compound is stable and non-adsorptive to membranes; otherwise, prepare fresh solutions aseptically.

• Stability monitoring:

  • Periodically assess by HPLC/UHPLC or LC–MS for degradation products, especially after repeated thawing or prolonged room-temperature exposure.

• Definitive instructions:

  • For authoritative storage limits, shelf life, and solution stability, consult the item’s CoA/Spec Sheet and SDS.

Structure and Identity

Brief overview: Epivogeloside (SKU E988582) is offered as a research-use small molecule/compound library member. Structural specifics are not fully provided in the product data.

• Item-specific (Product Data):

  • Product Name: Epivogeloside
  • CAS: 118627-52-4
  • PubChem CID: 14192590
  • InChIKey: 311656 (as provided)
  • 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/computed identifiers:

  • No additional structure identifiers are provided here. If needed, consult the CoA or authoritative databases for a definitive InChI, SMILES, and exact stereochemistry (literature/third-party sources).

• General chemistry context (not item-specific):

  • The suffix “-oside” often denotes a glycoside scaffold in natural products nomenclature, implying a sugar moiety linked to an aglycone via a glycosidic bond (general knowledge). However, without an item-specific structure, do not assume functional groups or ring systems for this product.
  • For cheminformatics workflows, ensure harmonization of identifiers (CAS, CID, InChIKey) and verify stereochemical descriptors from primary data sheets prior to registration or use in QSAR/virtual screening pipelines.

• 2D structural description:

  • Not provided for this specific item. Obtain structural diagrams and stereochemical annotations from CoA/Spec Sheet before planning structure-dependent experiments.

Synthetic Utility

Based on the available information, Epivogeloside is offered as a screening/library compound rather than a synthetic reagent or building block.

• Item-specific (Product Data):

  • No functional group annotations or reactivity guidance are provided for this item; structural details are Not specified for this item; refer to CoA/Spec Sheet.

• General considerations (not item-specific):

  • Library members are typically used as-received for biological evaluation, not as substrates. Attempting derivatization without a confirmed structure and stability profile is discouraged.
  • If the structure becomes available and contains derivatizable handles (e.g., phenols, amines, carboxylates, glycosidic OH groups), common transformations might include acylation, alkylation, carbamate/urethane formation, or selective hydrolysis—subject to stereochemical and protecting-group control.
  • For analytical method development, understanding chromophores (UV absorbance) and ionization behavior (ESI±) aids LC–MS method selection and impurity profiling.

• Best practices:

  • Verify identity and purity by LC–MS and NMR before any synthetic modification.
  • Conduct micro-scale reactions first; monitor by LC–MS to avoid loss of scarce material.
  • Document any salt/base equivalents to express concentrations on a consistent molar basis.

• Note: Do not assume reactivity patterns for this specific item without confirmed structural information from the CoA/Spec Sheet.

Target Specificity

No target or selectivity information is provided for this product.

• Item-specific (Product Data):

  • Target, mechanism, EC50/IC50, and off-target profiles: Not specified for this item; refer to CoA/Spec Sheet.

• General guidance (not item-specific):

  • If used in biological screens, determine preliminary target specificity through counter-screens, orthogonal assay formats, and biophysical binding assays (e.g., SPR, ITC, MST) after a hit is observed.
  • Evaluate potential assay interference (fluorescence/absorbance overlap, redox activity, aggregation) using standard control assays (e.g., detergent sensitivity, light scattering, redox quenchers).

• Documentation:

  • Record provenance, batch number, and analytical confirmation so that any observed biological effect can be attributed to a verified material.

• Note: No claims are made regarding biological activity or therapeutic potential for this item.