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
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
462.400 g/mol
XLogP3
0.000
Hydrogen Bond Donor Count
4
Hydrogen Bond Acceptor Count
12
Rotatable Bond Count
4
Exact Mass
462.08 Da
Monoisotopic Mass
462.08 Da
Topological Polar Surface Area
170.000 Ų
Heavy Atom Count
33
Formal Charge
0
Complexity
776.000
Isotope Atom Count
0
Defined Atom Stereocenter Count
4
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
No tested application protocols are provided for this item. The notes below are general, non-binding guidance for handling small molecules in screening workflows:
Stock preparation: Dissolve in dry DMSO to prepare a concentrated stock (e.g., 10–50 mM). Vortex and, if needed, sonicate gently. Filter (0.22 μm PTFE) if particulate remains.
Plate handling: Use low-binding polypropylene tubes/plates. Minimize freeze–thaw of DMSO stocks by aliquoting.
Assay dilution: Add DMSO stock to assay buffer/media last to reduce precipitation. Keep final DMSO ≤0.5–1% v/v unless the assay tolerates more.
Stability checks: Run time-zero vs. incubated LC–MS or HPLC to assess stability in assay matrix. For glycosides, avoid prolonged exposure to extreme pH.
Analytical QC: Verify identity and purity by LC–MS prior to critical studies. Record exact lot/CoA details for reproducibility.
For any application requiring specific conditions (e.g., enzymology, cell assays), develop and validate a protocol tailored to this compound after confirming its structure and solubility profile.
Biological Roles
Item-specific biological roles are not provided and should not be inferred. The following is general literature context for glycosylated natural products and O‑methylated derivatives; it is not a claim for this specific item.
Natural product context (general): Many plant secondary metabolites occur as glycosides, where sugar attachment modulates solubility, transport, and storage. O‑Methylation of phenolic or sugar hydroxyls can fine-tune lipophilicity and metabolic stability.
Biochemical interactions (general): Glycosides often interact with carbohydrate-recognition domains, transporters, or enzymes that process glycosidic linkages. Phenolic glycosides may exhibit antioxidant redox behavior in vitro, though outcomes depend strongly on substitution patterns and assay conditions.
Metabolic fate (general): In biological systems, glycosides can undergo enzymatic hydrolysis (glycosidases), O‑demethylation (oxidative), and phase II conjugations (e.g., glucuronidation, sulfation) after aglycone release.
Assay considerations: High polarity can limit passive permeability; observed activity in cell assays may depend on active transport or assay media composition. Protein binding and aggregation at high concentrations can confound readouts.
No claims are made regarding physiological effects or therapeutic properties of 3-O-MethylduchesideA. This product is supplied strictly for research use only.
Buffer Applications
This product is a small molecule and is not itself a buffering agent. Specific buffer systems for its use are not defined for this item.
Practical guidance (general):
If used in biochemical assays, prepare a concentrated DMSO stock and dilute into the assay buffer (e.g., phosphate, HEPES, Tris) while keeping final organic co-solvent low (≤0.5–1% v/v).
Avoid strongly acidic or basic buffers if the compound contains acid‑labile glycosidic linkages, as hydrolysis may occur (literature/general).
Pre-filter or centrifuge after dilution to remove any precipitate; adjust co-solvent proportion as needed.
Item-specific buffer compatibility and pH stability are not specified for this product; verify empirically.
Green Alternatives
Because 3-O-MethylduchesideA is a solid small molecule rather than a solvent or reagent used in bulk, “green alternatives” primarily concern the choice of solvents and methods used with it. Guidance below is general/literature-based and not item-specific.
Greener solvent choices for dissolution and chromatography:
Prefer ethanol, isopropanol, and water (where feasible) over more hazardous solvents.
For LC separations, consider water–ethanol or water–acetone gradients as alternatives to acetonitrile or methanol when performance allows.
Derivatization/transformations:
Favor enzymatic or biocatalytic transformations for glycosidic modifications rather than harsh chemical conditions.
Employ microwave-assisted or flow methods to reduce energy/time and potential waste streams.
Workup and purification:
Use solid-phase extraction (SPE) to minimize solvent volumes.
Recycle solvents where compatible with purity requirements.
Comparison (general):
Methanol vs. Ethanol: Ethanol is less toxic and can often substitute for MeOH in preparative chromatography with minor method re-optimization.
Acetonitrile vs. Acetone: Acetone is more benign but may alter selectivity and UV cutoffs; validate carefully.
Trade-offs: Greener systems may require longer runs or offer different selectivity. Validate recovery and stability of the compound under modified conditions.
Always balance environmental benefits with compound stability (avoid conditions that promote glycosidic hydrolysis).
Pharmaceutical Uses
No pharmacopeial status, excipient role, or formulation specifications are provided for this item. This product is offered for research use only.
General research-related context (not item-specific, no therapeutic claims):
Reference material: Can serve as a research reference standard for analytical method development (e.g., LC–MS, HPLC) when investigating related natural-product families.
Preformulation screening: Solubility, stability, and polymorph assessment may be performed to support discovery-stage studies; however, no clinical or manufacturing claims are made for this specific compound.
Formulation experiments: For in vitro work, compound is often dosed from DMSO stocks into aqueous media; for in vivo preclinical studies (if conducted under appropriate approvals), co-solvent/surfactant systems may be explored. Item-specific guidance is not provided here and must be defined by the research team.
No claims are made regarding therapeutic use, efficacy, or safety in humans or animals.
Physical Properties
Item-specific physicochemical data are not provided in the product record and should be confirmed on the CoA/Spec Sheet.
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 point / 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.
Solubility: Not specified for this item; refer to CoA/Spec Sheet.
LogP / pKa: Not specified for this item; refer to CoA/Spec Sheet.
General literature context for glycosylated natural products (not item-specific):
Such compounds are commonly polar and often show good solubility in DMSO and methanol, variably in water, and poor solubility in nonpolar solvents (literature, general).
Many glycosides decompose before boiling; they may exhibit a broad melting/decomposition range.
The presence of multiple hydroxyls often yields low logP and potential H-bond donor/acceptor behavior (literature, general).
Please consult the CoA/SDS for definitive, item-specific physical parameters before method development.
Quality and Grades
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Interpretation and guidance:
When a product is listed without an explicit grade, users should consult the Certificate of Analysis (CoA) for batch-specific purity (e.g., HPLC area %, NMR purity) and any residual solvent or water content determinations. If your application is analytical (e.g., reference standard) or biological screening, request chromatographic and spectral data to confirm identity and purity.
Typical quality dimensions for small-molecule library members include:
Identity confirmation: 1H/13C NMR, HRMS, and sometimes LC–MS purity traces.
Chromatographic purity: HPLC/UPLC with UV or MS detection; report method details (wavelength, gradient) for context.
Residuals: Volatile impurities, residual solvents (GC headspace), water (Karl Fischer), and inorganic residues (ash). For this specific item, values are not specified and should be confirmed on the CoA.
Stabilizers/Inhibitors: Not specified for this item. If present in a batch, inhibitors should be disclosed on the CoA and may influence downstream reactions or bioassays.
If your workflow is GxP-aligned or requires traceability, request lot-specific documentation (CoA, spectra, and if needed, impurity profiles) before use.
Reaction and Applications
Manufacturer-supplied application specifics are not provided. The following reflects common uses of glycosylated natural products in research contexts (literature/general guidance):
Chemical biology and screening: Utilized as a member of small-molecule libraries for phenotypic or target-based assays. Polar glycosides often modulate transport or enzyme binding profiles.
Reference standard / comparator: Employed as a benchmark in metabolomic profiling or LC–MS method development when the compound is part of a known natural-product family.
Derivatization studies:
Deprotection/transformation: O‑methyl groups can be diagnostic handles; selective demethylation (e.g., BBr3/BCP in non-aqueous media) or further etherification/acylation allows SAR exploration. Conditions must be tailored to protect labile glycosidic bonds (avoid strong acids/bases or elevated temperatures that induce hydrolysis).
Glycosidic stability tests: Mild acid (aq. HOAc) vs. enzyme (β‑glucosidases, if applicable) to study hydrolytic pathways.
Analytical methods: Reverse-phase HPLC/UPLC with aqueous-organic gradients (water/MeOH or water/ACN with 0.1% formic acid or ammonium acetate) and ESI‑MS detection are commonly used for such analytes. Multiple hydroxyls favor positive and negative ESI responses (literature/general).
Practical tips:
Maintain dry, neutral conditions during manipulations to minimize undesired hydrolysis.
For purification, preparative RP-HPLC is often preferred over normal-phase chromatography due to polarity and tailing concerns.
Item-specific validated applications are not specified for this product.
Reaction Conditions
No item-specific reaction conditions are provided. The following are general, literature-based guidelines for handling and transforming O‑methylated glycosides and related polyhydroxylated natural products:
Hydrolysis sensitivity: Glycosidic bonds can cleave under acidic (mineral acids, heat) or basic conditions (strong base, prolonged times). If hydrolysis is undesired, maintain near-neutral pH, low water activity, and moderate temperatures.
(De)methylation:
Aryl O‑demethylation: BBr3 in DCM at −78 to 0 °C, then quench at low temperature (literature); monitor to avoid glycosidic cleavage. Alternative milder agents include BCl3 or TMSI.
Methylation of phenols/alcohols: MeI/Ag2O or Me2SO4 with base in polar aprotic solvents; ensure compatibility with other sensitive groups.
Acylation:Ac2O/pyridine or acid chlorides at 0–25 °C to give mono-/polyacylated derivatives; selectivity controlled by protecting groups and sterics.
Oxidation/reduction: Benzylic/phenolic oxidations (e.g., DDQ, TEMPO systems) and selective reductions (e.g., hydrogenolysis of benzyl protections) must consider sugar stability and avoid over-oxidation.
Workup/purification: Prefer RP-HPLC or flash chromatography on reversed-phase media with water–MeOH/ACN gradients; avoid strong acid modifiers if hydrolysis is a concern.
All conditions above are general literature guidance and must be tailored after confirming the exact structure of this item. Pilot-scale trials and analytical monitoring (LC–MS, TLC, NMR) are essential.
Safety and Handling
Safety information is incomplete in the product record. Always consult the SDS for authoritative guidance.
GHS Classification / Signal Word / H-Statements / Pictograms: Not specified for this item; refer to SDS.
General hazards (literature/general for small organic glycosides): Typically low volatility solids with low inhalation risk compared to solvents; possible irritation on contact or ingestion. Do not assume non-hazardous—handle as potentially harmful.
PPE: Lab coat, safety glasses or splash goggles, and appropriate chemically resistant gloves (e.g., nitrile). Use in a fume hood to minimize dust/aerosol exposure.
Handling notes:
Avoid moisture if the compound is hydrolysis-sensitive; keep container tightly closed.
Prevent dust formation; use antistatic measures when weighing fine powders.
Incompatibilities (general): Strong acids/bases may promote glycosidic bond cleavage or transglycosylation; strong oxidizers may oxidize phenolic/benzylic positions.
First aid (overview):
Skin/eye contact: Rinse with water for several minutes; remove contaminated clothing; seek medical attention if irritation persists.
Inhalation: Move to fresh air; seek medical attention if symptoms occur.
Ingestion: Rinse mouth; do not induce vomiting; seek medical advice.
Fire safety: Use CO2, dry chemical, or foam. Many organics can burn; combustion may generate CO/CO2 and irritating fumes.
Defer to the official SDS for all binding safety classifications and emergency measures.
Solvent Selection
Item-specific solubility is not provided. The following guidance is based on literature/general behavior of polyhydroxylated glycosides and should be verified experimentally.
DMSO, DMF: often excellent for initial stock solutions (screening libraries).
Methanol, ethanol: frequently good; may co-solvate with water.
Water or aqueous buffers: variable; may require pH adjustment or co-solvent (10–50% MeOH/EtOH) to achieve target concentrations.
Poor in nonpolar solvents (e.g., hexane, toluene) for most glycosides.
Dielectric/behavior (literature, general): Better dissolution with increasing solvent polarity and H-bonding capacity. Aggregation can occur at high concentrations in water; consider gentle warming and sonication.
Formulation tips for screening:
Prepare a concentrated DMSO stock (e.g., 10–50 mM), then dilute into assay medium, keeping final DMSO ≤0.5–1% v/v to maintain biological compatibility.
If crystallization occurs on dilution, increase co-solvent fraction or pre-warm the medium.
When to choose alternatives: If aqueous delivery is required and solubility is marginal, consider cyclodextrin inclusion, pH adjustment (if ionizable groups present), or mixed solvent systems.
Note: Confirm actual solubility for this item with a small-scale test; defer to the CoA for any vendor-supplied solubility data.
Shipped In: Not specified for this item; refer to CoA/Spec Sheet.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Reconstitution and handling (general guidance for small molecules; verify empirically for this item):
Solvent selection: Start with dry DMSO or methanol to prepare a concentrated stock solution. Water solubility is variable for glycosides; if needed, co-solvents or mild warming may assist dissolution.
Concentration and aliquots: Prepare 10–50 mM DMSO stocks and aliquot to avoid repeated freeze–thaw. Label with lot number and date.
Short-term stability: At room temperature and protected from moisture/light, many small molecules are stable for days to weeks; however, this is not specified for this item. Confirm by LC–MS/HPLC.
Long-term storage: If extended storage is required, consider 2–8 °C or −20 °C in desiccated, light-protected conditions as a conservative practice for library compounds (general guidance, not item-specific).
Freeze–thaw: Minimize cycles; store aliquots to preserve integrity. Inspect for precipitation or discoloration upon thawing.
All item-specific stability, solubility, and reconstitution parameters should be confirmed from the product’s CoA and SDS. Research use only.
Structure and Identity
Brief overview: 3-O-MethylduchesideA is presented as a small-molecule library member. Item-specific structural identifiers are largely not provided in the product data.
Product Name: 3-O-MethylduchesideA (SKU: O965982)
CAS: 10457042 (as provided)
PubChem CID: 10457042 (as provided)
InChIKey: 357325 (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.
Structural features (general context):
The name suggests a glycosylated natural product where a “Ducheside A” scaffold bears a methyl substituent at the 3‑O position. In many natural products, “3‑O‑methyl” denotes methylation of a phenolic or glycosidic hydroxyl (literature, general).
Likely functional group classes (literature/general for such glycosides): multiple hydroxyls, acetal/glycosidic linkages, and possible aromatic/phenolic moieties. Exact stereochemistry and ring topology are not specified for this item.
2D structure description (generic, literature-based for glycosides):
A polyoxygenated aglycone linked via an O‑glycosidic bond to one sugar unit (or more), with a methyl ether at the 3‑O position. Without a definitive SMILES/InChI, the precise ring count, anomeric configuration, and substitution pattern cannot be stated for this item.
Synthetic Utility
Without item-specific structural details, the synthetic discussion below is limited to general features typical of O‑methylated glycosides and polyphenolic natural products (literature/general):
Functional handles: Multiple alcohols (free or masked), hemiacetal/acetal (glycosidic) centers, and at least one methyl ether at the 3‑O position can serve as points for selective transformation.
Protecting-group logic: Orthogonal protection (e.g., silyl ethers, benzyl/PMB, acyl groups) is commonly required to achieve site-selective modifications on richly functionalized scaffolds.
Selective (de)methylation: BBr3, BCl3, or TMSI can effect aryl O‑demethylation under controlled conditions; compatibility with glycosidic linkages must be carefully validated. Oxidative methods (e.g., CAN) may cleave certain ethers but risk over-oxidation.
Glycoside modifications: Enzymatic glycosidases (if substrate-compatible) provide mild deprotection routes; glycosyl transferases or Koenigs–Knorr-type chemistry can introduce alternative sugars or anomeric configurations on related scaffolds.
Late-stage diversification: Acylations (e.g., with acyl chlorides/anhydrides), carbonate formation, and carbamate linkages can modulate polarity and stability for SAR.
Analytical control: Rich functionality demands rigorous LC–MS monitoring and 2D NMR (HSQC/HMBC/NOESY) to confirm regio- and stereochemical outcomes.
For this specific item, definitive reactivity patterns and protecting-group strategies should be based on a confirmed structure from the CoA or primary literature.
Target Specificity
This product is a small molecule and not an antibody, protein, or oligonucleotide. No target or epitope specificity is applicable.
Item-specific target/epitope data: Not applicable.
If used in target-based assays, any observed activity is assay- and context-dependent and should be validated with orthogonal methods.
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