Ptelatoside b - ≥98% , CAS No.90852-99-6

CAS: 90852-99-6 Cat. No.: P1018149 Formula: C₂₀H₂₈O₁₀ Peso molecolare: 428.400

GRADE & PURITY ≥98%

Storage

Room temperature

Specifications

Specifiche e purezza

≥98%

Condizioni di conservazione di stoccaggio

Room temperature

Purezza

≥98%

Nomi e identificatori

• Sorrisi canonici: C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2OC3=CC=C(C=C3)C=C)CO)O)O)O)O)O
• IUPAC Name: (2S,3R,4R,5R,6S)-2-[(2S,3R,4S,5S,6R)-2-(4-ethenylphenoxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-6-methyloxane-3,4,5-triol
• InChIKey: DIBOBJSTTKLQQV-QLDOSHOCSA-N
• INCHI: 1S/C20H28O10/c1-3-10-4-6-11(7-5-10)28-20-18(16(25)14(23)12(8-21)29-20)30-19-17(26)15(24)13(22)9(2)27-19/h3-7,9,12-26H,1,8H2,2H3/t9-,12+,13-,14+,15+,16-,17+,18+,19-,20+/m0/s1
• Peso molecolare: 428.400

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Classe Organooxygen compounds
      • Subclass Carbohydrates and carbohydrate conjugates
        • Level5 Glycosyl compounds
          • Level6 Phenolic glycosides

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Classe: Organooxygen compounds
• Subclass: Carbohydrates and carbohydrate conjugates
• Intermediate Tree Nodes: Glycosyl compounds
• Direct Parent: Phenolic glycosides
• Alternative Parents: O-glycosyl compounds Disaccharides Styrenes Phenoxy compounds Phenol ethers Oxanes Secondary alcohols Polyols Oxacyclic compounds Acetals Primary alcohols Hydrocarbon derivatives
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Phenolic glycoside - Disaccharide - O-glycosyl compound - Phenoxy compound - Styrene - Phenol ether - Monocyclic benzene moiety - Benzenoid - Oxane - Secondary alcohol - Acetal - Oxacycle - Organoheterocyclic compound - Polyol - Alcohol - Primary alcohol - Hydrocarbon derivative - Aromatic heteromonocyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.
• 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

Proprietà chimiche e fisiche

• Peso molecolare: 428.400 g/mol
• XLogP3: -0.200
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 6
• Exact Mass: 428.168 Da
• Monoisotopic Mass: 428.168 Da
• Topological Polar Surface Area: 158.000 Ų
• Heavy Atom Count: 30
• Formal Charge: 0
• Complexity: 554.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 10
• 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 application protocols specific to this SKU are provided in the Product Data. As a small-molecule reference standard, typical procedures include:

• Reference standard preparation: Prepare a concentrated stock in DMSO or methanol (as solubility permits), filter (0.22 µm PTFE) if needed, and dilute into assay medium immediately before use. Verify concentration by UV or quantitative NMR using an internal standard (general guidance).
• LC–MS method development: Optimize gradient (water/MeCN or water/MeOH), ionization mode, and source parameters. Use a stability-indicating method to monitor potential hydrolysis.
• Enzymatic assay setup: If used as a glycosidase substrate, select an appropriate buffer (pH 4.5–6.5 commonly for β-glucosidases), include controls without enzyme, and quench aliquots for LC–MS analysis.

These are general research workflows; adapt and validate for your system. For any item-specific instructions, refer to the CoA or method sheet if supplied.

Biological Roles

Item-specific biological functions are not provided in the Product Data. The following context reflects general properties of plant glycosidic natural products and should not be taken as clinical or therapeutic claims.

• Ecological function (literature, general): Many glycosides serve as defense metabolites, storage forms of active aglycones, or transport-compatible conjugates that increase water solubility in planta.
• Biochemical behavior: Glycosylation typically modulates solubility, stability, and subcellular localization. Enzymatic glycosidases can regenerate the aglycone under specific conditions, impacting activity in biochemical assays.
• Metabolism: In model systems, glycosides are subject to phase I/II biotransformations (hydrolysis, oxidation, further conjugation). In vitro studies often investigate enzyme specificity and kinetics using purified glycosides as substrates.
• Analytical relevance: Ptelatoside b, as a defined small molecule, may be used as a reference standard in metabolomic profiling, aiding annotation of plant extracts or biosynthetic pathway studies.

Note: No biological role is assigned to this product for any therapeutic or diagnostic purpose. Use is strictly for research-level biochemical and analytical investigations.

Buffer Applications

This product is a small-molecule natural product standard and is not a buffering agent. Therefore, conventional buffer formulation guidance (pH ranges, capacity curves) is not applicable.

Practical notes for analytical work (general):

• If preparing solutions of Ptelatoside b for assays, select the assay buffer based on the biological system (e.g., phosphate, HEPES) and confirm the compound’s stability in that buffer.
• Use minimal amounts of cosolvent (DMSO, ethanol) to aid dissolution, keeping final organic content consistent across controls.

Item-specific buffer compatibility data are not provided; verify experimentally.

Green Alternatives

While Ptelatoside b is the target material (not a solvent), greener choices pertain to the solvents and methods used to handle, purify, and analyze it. The guidance below is general and should be validated for your method.

• Preferred greener solvents for handling/extraction:
  • Replace chlorinated solvents (DCM, CHCl3) with ethyl acetate where feasible.
  • Use ethanol or isopropanol in place of methanol when extraction efficiency and selectivity permit.
  • Favor water-rich mobile phases and reduce acetonitrile consumption in HPLC by optimizing gradients and column efficiency.
• Energy and waste minimization:
  • Employ solid-phase extraction (SPE) for cleanup to reduce bulk solvent use.
  • Use UHPLC with smaller columns and higher efficiency to cut solvent volumes.
• Tradeoffs:
  • Ethanol may reduce extraction of highly polar glycosides compared with methanol; water cosolvent ratios may need optimization.
  • Ethyl acetate is less polar than DCM and can lower recovery for very polar species; consider n-butanol or ethyl lactate as intermediate-polarity options.

Comparison (general):

• Ethanol: renewable, low toxicity; slightly lower polarity than methanol; may need higher water content.
• Ethyl acetate: biodegradable, low toxicity; limited capacity for highly polar analytes.
• Acetonitrile: excellent chromatographic performance but higher environmental burden; reduce or recover via solvent recycling when possible.

Pharmaceutical Uses

No pharmacopeial status or excipient role is provided for this item. This product is sold strictly for research use and is not intended for human or veterinary applications.

Research/manufacturing context (general):

• Reference standard in analytical development, e.g., stability-indicating HPLC for natural product-containing raw materials.
• Impurity/degradation marker for plant-derived ingredients where the compound may occur naturally.
• Potential use in forced-degradation studies to understand hydrolytic and photolytic pathways of related glycosidic materials.

If your workflow requires compliance with specific monographs or compendial references, confirm suitability and documentation (purity basis, residual solvent data) via the CoA for this batch.

Physical Properties

Item-specific physicochemical parameters have not been provided for this product listing. Where needed, consult the CoA or SDS.

• 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 (MP): Not specified for this item; refer to CoA/Spec Sheet.
• Boiling point (BP): Not applicable for many glycosides due to thermal decomposition before boiling; item-specific data not specified.
• Density: Not specified for this item; refer to CoA/Spec Sheet.
• Solubility: Not specified for this item; refer to CoA/Spec Sheet.
• LogP/logD: Not specified for this item; refer to CoA/Spec Sheet.
• pKa: Not specified for this item; refer to CoA/Spec Sheet.
• Refractive index/UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.

General, literature context for glycosidic natural products (not item-specific):

• Glycosides often exhibit good solubility in polar protic solvents (e.g., methanol, ethanol, water mixtures) and in DMSO, while being poorly soluble in nonpolar hydrocarbons.
• They may show broad UV absorbance when the aglycone is aromatic (e.g., phenolic), enabling HPLC-UV detection at 210–280 nm (method-dependent).
• Solid glycosides typically decompose before boiling and may have high melting ranges with charring.

Please verify any working properties empirically at small scale and confirm against the product’s CoA for this specific SKU.

Quality and Grades

Grade, purity, and stabilizer information are not specified in the Product Data for this SKU.

• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet. The CoA will define assay method (e.g., HPLC area%), residual solvents, and limits for related substances where applicable.
• Identity confirmation: Natural products are commonly verified by HRMS, 1H/13C NMR, and HPLC (UV/ELSD/MS). For glycosides, the presence of anomeric signals and characteristic coupling patterns often supports structural assignment (general practice).
• Chromatographic behavior: If intended for analytical workflows (e.g., LC–MS reference standard), low non-volatile residue and defined retention behavior are important; refer to the CoA for the validated analytical method.
• Stabilizers/antioxidants: Not specified for this item; refer to CoA/Spec Sheet. Many glycosides do not require stabilizers but can benefit from desiccation and protection from prolonged heat and strong light (general guidance).
• Lot traceability: Each lot should be supported by a CoA with batch number, release date, and analytical summary to facilitate method transfer and regulatory documentation in research settings.

For precise suitability in regulated workflows (e.g., QC reference), confirm specification alignment (purity basis, water content method, residual solvent limits) directly on the CoA.

Reaction and Applications

Manufacturer-specific application notes are not provided for this SKU. Based on common practice with glycosidic natural products, Ptelatoside b can be used in research as a reference standard, as a probe for metabolism or hydrolysis studies, and as a substrate for selective transformations.

• Analytical/standards:
  • Calibration and retention-time markers for LC–MS metabolomics or dereplication workflows targeting plant glycosides.
  • Method development for stability-indicating assays under acidic, basic, thermal, and photolytic stress.
• Chemical transformations (general):
  • Hydrolysis: Acidic (e.g., TFA, HCl aq) or enzymatic (glycosidases) cleavage of the glycosidic bond to release the aglycone and sugar.
  • Acylation/silylation: Temporary protection of hydroxyls (Ac2O/pyridine, TMSCl/imID) for derivatization or GC analysis of fragments.
  • Glycosylation editing: Exchange or extension of sugar units via neighboring-group-participating donors (Koenigs–Knorr, Schmidt, or modern catalytic glycosylations) on the aglycone (literature context).
• Biotransformations: Microbial or enzyme-mediated regioselective oxidation, hydrolysis, or glycosyl transfer for SAR or biosynthetic studies.
• Assay use: Substrate in enzyme kinetics (β-glucosidase, β-galactosidase, etc., depending on the linkage), and as a comparator in transport or permeability studies (in vitro), subject to solubility.

All applications are for laboratory research only. Verify identity and purity with CoA prior to quantitative use.

Reaction Conditions

No item-specific synthetic or processing conditions are provided. The following are general literature conditions for common manipulations of glycosidic natural products and should be optimized for the specific structure.

• Acidic hydrolysis: Aqueous HCl (0.1–2 M) or TFA (0.1–1 M) at 40–80 °C for 0.5–6 h to cleave O-glycosidic bonds; monitor by LC–MS. Overexposure may degrade the aglycone (literature guidance).
• Enzymatic hydrolysis: β-Glycosidases in acetate/phosphate buffer (pH 4.5–6.5) at 25–37 °C; reaction times from 0.5–24 h depending on enzyme and linkage.
• O-Acetylation: Ac2O/pyridine (or DMAP catalysis) in DCM or pyridine at 0–25 °C, 0.5–4 h; quenched with MeOH/H2O; affords peracetylated derivatives for characterization.
• Silylation: TMSCl/imidazole in DMF at 0–25 °C; minutes to hours for derivatization prior to GC of hydrolysates.
• Glycosylation (assembly): Protected sugar donors (trichloroacetimidates or halides) with Lewis acids (TMSOTf, BF3·Et2O) in DCM/Et2O at −78 to 0 °C; stereocontrol via neighboring groups (literature).
• Analytical prep: DMSO stock solutions diluted into 50:50 water:MeCN with 0.1% formic acid for LC–MS; verify ionization in ESI± modes (general method note).

All conditions are provided as general literature guidance and are not specifications for this item.

Safety and Handling

The Product Data does not include hazard classification for this item; always consult the SDS provided with the batch for authoritative information.

• GHS classification / pictograms / signal word / H-statements: Not specified for this item; refer to SDS.
• General laboratory precautions:
  • Handle in a fume hood or well-ventilated area to avoid dust/aerosol inhalation.
  • Wear appropriate PPE: lab coat, safety glasses, and suitable chemical-resistant gloves.
  • Avoid contact with oxidants and strong acids/bases unless reaction conditions require; glycosidic bonds can be acid- or enzyme-labile (general chemistry note).
• Incompatibilities (general): Strong mineral acids may hydrolyze O-glycosides; strong bases can cause elimination or epimerization of carbohydrate centers.
• First aid overview (consult SDS):
  • Inhalation: Move to fresh air; seek medical advice if symptoms persist.
  • Skin/eye contact: Rinse with water for several minutes; remove contaminated clothing; seek medical attention if irritation continues.
  • Ingestion: Rinse mouth; do not induce vomiting; obtain medical attention.
• Spill response: Avoid dust generation; dampen and collect with inert absorbent; dispose per institutional and local regulations.
• Fire: If combustible, use CO2, dry chemical, or foam. Many organic solids may burn and form irritating fumes.

For research use only. Not for human or animal use.

Solvent Selection

Item-specific solubility and solvent compatibility are not provided in the Product Data. The following guidance is general for glycosidic natural products and should be verified experimentally.

• Polarity/miscibility (general):
  • Often soluble in polar protic solvents (methanol, ethanol) and in DMSO; variable solubility in water depending on substitution and aglycone.
  • Limited solubility in aprotic nonpolar media (hexanes, toluene).
• Analytical preparation:
  • For LC–MS: Start with DMSO stock (e.g., 5–20 mg/mL) and dilute into water:acetonitrile with 0.1% formic acid as needed. Verify stability against acid/base modifiers.
  • For HPLC-UV: Methanol/water or acetonitrile/water gradients commonly used; detection wavelength depends on aglycone chromophore (general literature).
• Reaction media (if derivatization is planned):
  • Protecting-group chemistry on sugars typically uses anhydrous aprotic solvents (DMF, DCM) with catalytic acids/bases; initial dissolution may require co-solvents.
• When to choose alternatives:
  • If aqueous solubility is poor, consider DMSO or DMF cosolvent additions. For greener profiles, ethanol or isopropanol can sometimes replace methanol or acetonitrile for preparative work (see Green Alternatives).

Note: Confirm actual solubility and stability with small-scale tests; consult CoA for any item-specific recommendations.

Storage and Reconstitution

• Storage conditions (as provided): Room temperature.
• Shipped in: Not specified for this item; refer to CoA/Spec Sheet.

General best practices for glycosidic natural products (not item-specific specifications):

• Store in a tightly sealed, inert container with desiccant and protect from prolonged light exposure. If long-term storage is planned, consider refrigerated storage (2–8 °C) as a precaution unless contraindicated by the CoA.
• Avoid repeated exposure to high humidity; many glycosides are hygroscopic to some extent.

Reconstitution (general guidance):

• Solvent choice depends on solubility; commonly DMSO, methanol, ethanol, or aqueous mixtures are used. Item-specific solubility: Not specified for this item; verify experimentally.
• Prepare concentrated stocks (e.g., 5–20 mg/mL where soluble) and aliquot to minimize freeze–thaw and headspace.
• For aqueous applications, first dissolve in a miscible organic solvent (DMSO/MeOH), then dilute into buffer with vigorous mixing to avoid precipitation. Filter through 0.22 µm if required for analytical use.

Always refer to the batch-specific CoA/SDS for definitive guidance on storage stability and handling.

Structure and Identity

Ptelatoside b is described in phytochemical literature as a plant-derived small molecule (a specialized metabolite), commonly classified among glycosidic natural products. The exact structural identifiers for this catalog item are not fully provided in the current Product Data.

• CAS: 90852-99-6 (provided)
• PubChem CID: 130179 (provided)
• InChIKey: 64036 (incomplete as provided; typical InChIKeys are 27 characters). Not specified for this item; refer to CoA/Spec Sheet.
• 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, literature context):

• Many compounds designated as “-side” are glycosides, featuring a sugar moiety (e.g., β-D-glucosyl) linked via a glycosidic bond to an aglycone (phenolic, terpenoid, or other scaffold). This implies multiple hydroxyl groups, potential acetal/hemiacetal centers, and several stereocenters (literature, class-level expectation).
• The 2D description of typical glycosides comprises a polyhydroxy pyranose or furanose ring tethered to an aglycone via an O-glycosidic linkage; other linkages (C-, N-, S-) are context-dependent (literature).

Important: Item-specific identifiers beyond CAS/CID are not specified in the Product Data and should be confirmed against the accompanying CoA/SDS for this batch.

Synthetic Utility

Although Ptelatoside b is primarily a target molecule rather than a building block, glycosidic natural products can participate in a range of transformations useful for structure–activity or analytical derivatization studies.

• Key functional motifs (general): Multiple secondary alcohols (sugar residues), a glycosidic acetal center (often anomeric), and the aglycone functional group family (e.g., phenol, alcohol, terpenoid, etc., class-dependent).
• Typical transformations:
  • Selective O-acylation/benzylation/silylation for protection and subsequent site-selective modification.
  • Hydrolysis of the glycosidic bond (acidic or enzymatic) to access the aglycone for separate functionalization, followed by reglycosylation.
  • Oxidation/reduction on aglycone substituents, or periodate cleavage on suitably configured sugar diols (for mapping or derivatization).
  • Click handles: Installation of azide/alkyne tags on the sugar hydroxyls for conjugation and analytical tracking.
• Retrosynthetic perspective: Disconnection at the anomeric linkage enables modular assembly from a protected sugar donor and aglycone acceptor, utilizing neighboring group participation for stereocontrol (Koenigs–Knorr, Schmidt, or catalytic glycosylation methods).

These strategies are general to glycosides; consult primary literature for conditions appropriate to the exact structure of Ptelatoside b.

Target Specificity

Not applicable. This product is a small-molecule natural product standard, not an antibody or biological reagent with defined antigen/epitope targeting.

• Item-specific target details (antigen, clone, isotype, species reactivity): Not applicable/not provided.