Acanthopanaxoside B , CAS No.915792-03-9

CAS: 915792-03-9 Cat. No.: A965995 PubChem CID: 11993928
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Spezifikationen

Storage
Room temperature
Namen und Kennungen
Kanonisches Lächeln
CC1C(C(C(C(O1)OC2C(OC(C(C2O)O)OCC3C(C(C(C(O3)OC(=O)C45CCC(CC4C6=CCC7C8(CCC(C(C8CCC7(C6(CC5)C)C)(C)C)OC9C(C(C(CO9)O)O)OC1C(C(C(C(O1)CO)O)O)O)C)(C)C)O)O)O)COC(=O)C)O)O)O
IUPAC Name
[(2S,3R,4S,5S,6R)-6-[[(2R,3R,4R,5S,6R)-6-(acetyloxymethyl)-3,4-dihydroxy-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl] (4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[(2S,3R,4S,5S)-4,5-dihydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
InChIKey
NYFPVHPLEGGWHZ-DIUPZIBKSA-N
INCHI
1S/C61H98O27/c1-25-36(65)40(69)44(73)51(81-25)86-48-32(24-78-26(2)63)84-50(47(76)43(48)72)80-23-31-39(68)42(71)46(75)53(83-31)88-55(77)61-18-16-56(3,4)20-28(61)27-10-11-34-58(7)14-13-35(57(5,6)33(58)12-15-60(34,9)59(27,8)17-19-61)85-54-49(37(66)29(64)22-79-54)87-52-45(74)41(70)38(67)30(21-62)82-52/h10,25,28-54,62,64-76H,11-24H2,1-9H3/t25-,28-,29-,30+,31+,32+,33-,34+,35-,36-,37-,38+,39+,40+,41-,42-,43+,44+,45+,46+,47+,48+,49+,50+,51-,52-,53-,54-,58-,59+,60+,61-/m0/s1
Isomere SMILES
C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H](O[C@H]([C@@H]([C@H]2O)O)OC[C@@H]3[C@H]([C@@H]([C@H]([C@@H](O3)OC(=O)[C@@]45CC[C@@]6(C(=CC[C@H]7[C@]6(CC[C@@H]8[C@@]7(CC[C@@H](C8(C)C)O[C@H]9[C@@H]([C@H]([C@H](CO9)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O)C)C)[C@@H]4CC(CC5)(C)C)C)O)O)O)COC(=O)C)O)O)O
PubChem CID
11993928
MeSH-Eintrag
3-O-beta-D-glucopyranosyl-(1-2)-alpha-L-arabinopyranosyl oleanolic acid 28-O-alpha-L-rhamnopyranosyl-(1-4)-6-O-acetyl-beta-D-glucopyranosyl-(1-6)-beta-D-glucopyranosyl ester;acanthopanaxoside B

Erweiterte Daten

Taxonomic Classification

Taxonomy Tree

KingdomOrganic compounds
SuperclassLipids and lipid-like molecules
KlassePrenol lipids
SubclassTerpene glycosides
Intermediate Tree Nodes Triterpene glycosides
Direct ParentTriterpene saponins
Alternative Parents Triterpenoids  Oligosaccharides  O-glycosyl compounds  Oxanes  Dicarboxylic acids and derivatives  Secondary alcohols  Carboxylic acid esters  Polyols  Oxacyclic compounds  Acetals  Primary alcohols  Organic oxides  Hydrocarbon derivatives  Carbonyl compounds  
Molecular FrameworkAliphatic heteropolycyclic compounds
Substituents Triterpene saponin - Triterpenoid - Oligosaccharide - Glycosyl compound - O-glycosyl compound - Dicarboxylic acid or derivatives - Oxane - Secondary alcohol - Carboxylic acid ester - Polyol - Acetal - Carboxylic acid derivative - Oxacycle - Organoheterocyclic compound - Primary alcohol - Alcohol - Organooxygen compound - Hydrocarbon derivative - Organic oxide - Organic oxygen compound - Carbonyl group - Aliphatic heteropolycyclic compound
BeschreibungThis compound belongs to the class of organic compounds known as triterpene saponins. These are glycosylated derivatives of triterpene sapogenins. The sapogenin moiety backbone is usually based on the oleanane, ursane, taraxastane, bauerane, lanostane, lupeol, lupane, dammarane, cycloartane, friedelane, hopane, 9b,19-cyclo-lanostane, cycloartane, or cycloartanol skeleton.
External Descriptors Not available
3D-Struktur
Interaktives chemisches Strukturmodell





Zertifikate (CoA, COO, BSE/TSE und Analyse-Diagramm)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Chemische und physikalische Eigenschaften
Molekulargewicht1263.400 g/mol
XLogP3-0.700
Hydrogen Bond Donor Count14
Hydrogen Bond Acceptor Count27
Rotatable Bond Count16
Exact Mass1262.63 Da
Monoisotopic Mass1262.63 Da
Topological Polar Surface Area419.000 Ų
Heavy Atom Count88
Formal Charge0
Complexity2490.000
Isotope Atom Count0
Defined Atom Stereocenter Count32
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
The total count of all stereochemical bonds0
Covalently-Bonded Unit Count1
Lösungsrechner
Bewertungen

Kundenbewertungen

Application Protocols

No tested biological application protocols (e.g., WB, IHC, IF, FC) are provided for this item, as it is a small-molecule standard in a compound library.

  • Item-specific (Product Data)

    • Recommended working concentrations, positive controls, dilutions: Not specified for this item; refer to your internal method development and the CoA.
  • General guidance (analytical)

    • Prepare a concentrated stock (e.g., 1–10 mg/mL) in MeOH, EtOH, or DMSO depending on solubility, then dilute into mobile phase or assay buffer immediately before use.
    • For LC–MS quantitation, prepare serial dilutions gravimetrically, use amber vials, and document purity correction if assay <100% on the CoA.

This product is supplied for research use only; develop and validate protocols appropriate to your application.

Biological Roles
  • Item-specific (Product Data)

    • Biological/biochemical roles: Not specified for this item; for research use only.
  • Literature/general background (not specific to this SKU and not a medical/clinical claim)

    • Compounds termed “Acanthopanaxosides” are reported as plant secondary metabolites from Acanthopanax/Eleutherococcus species (family Araliaceae). Many are glycosylated natural products (e.g., saponins or lignan glycosides) implicated in plant defense, signaling, and adaptation to environmental stresses.
    • Glycosylation typically modulates solubility, transport, compartmentalization, and storage within plant tissues. Enzymatic cleavage (glycosidases) can release aglycones, altering bioactivity within the plant.
    • In biochemical research, purified glycosides are often employed as standards to investigate biosynthetic pathways (glycosyltransferases, oxidative tailoring enzymes) and to compare metabolite profiles across cultivars, tissues, and processing conditions.
  • Analytical implications

    • Multiple hydroxyl groups and carbohydrate moieties enable characteristic MS fragmentation (neutral losses of 162, 146, 132 Da, etc., depending on sugar), aiding annotation in metabolomics.
    • UV absorbance depends on the aglycone; lignan- or aromatic-containing glycosides typically absorb in the near-UV, whereas triterpenoid saponins may require ELSD/CAD or MS detection.

For any biological experimentation, this product is supplied strictly for research use only; no biological activity is asserted for this catalog item.

Buffer Applications

This compound is not a buffering reagent and is not typically used to prepare defined pH buffer systems.

  • Item-specific (Product Data)

    • No buffer-related specifications or applications are provided for this item.
  • Practical note (general)

    • If solutions are prepared for biochemical assays, use a suitable external buffer system (e.g., phosphate, HEPES, acetate) selected for the target pH and ionic strength. Maintain near-neutral pH to limit potential glycosidic hydrolysis for glycoside-like compounds.

Refer to assay-specific protocols for buffer composition; do not rely on the compound to provide buffering capacity.

Green Alternatives

When preparing solutions or conducting derivatizations with glycoside-like natural products, solvent choice strongly influences environmental footprint. The following guidance is general and not item-specific.

  • Prefer greener solvents where feasible

    • Water and ethanol (bio-derived) are strong first choices for stock solutions and analytical dilutions if solubility permits.
    • Replace DMF/DMAC/NMP with ethanol, isopropanol, or water–alcohol mixtures for sample handling where method compatibility allows.
  • Comparison (general guidance)

| Use case | Conventional option | Greener alternative | Trade-offs | |---|---|---|---| | Stock solutions for screening | DMSO | Ethanol or 50% EtOH/H2O | Lower solvating power; may need higher volumes or gentle heat | | LC–MS sample prep | ACN (HPLC grade) | EtOH or MeOH | ACN often gives sharper peaks; MeOH/EtOH may require method re-optimization | | Derivatization medium | Pyridine, CH2Cl2 | Ethyl acetate, 2-MeTHF (where compatible) | Reaction rates/selectivity can change; verify on small scale |

  • Process considerations
    • Minimize solvent volumes; use microscale operations and closed-vial sonication.
    • Implement solvent recovery (rotary evaporation with cold traps) and proper waste segregation.

Adopt greener options only after confirming the compound’s solubility and stability under the chosen conditions.

Pharmaceutical Uses

No excipient or pharmacopeial status is provided for this item; it is supplied for research use only.

  • Item-specific (Product Data)

    • Pharmaceutical/industrial grade designation: Not specified for this item; refer to CoA/Spec Sheet.
  • Research and manufacturing context (general; not a therapeutic claim)

    • Purified natural products are often used as analytical reference standards in quality control of botanical raw materials and extracts (e.g., system suitability, identity testing, and assay by HPLC/UPLC).
    • They may support method validation (specificity, linearity, precision, accuracy, robustness) for herbal material testing in R&D settings.
    • In preformulation or formulation science, glycoside standards can inform solubility and stability assessments of related matrices; however, no excipient role is asserted for this SKU.

Any use in manufacturing or quality control should be preceded by verification of identity, purity, and stability from the lot-specific CoA and conducted under appropriate quality systems.

Physical Properties
  • 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.
  • Not provided for this item (do not treat as specifications):

    • Melting point, boiling point, density, refractive index, pKa, logP/logD, UV cutoff, water content, residual solvents: Not specified for this item; refer to CoA/Spec Sheet.
  • Literature/general expectations for plant glycosides (not specifications for this SKU)

    • Physical state: Typically solid (often amorphous or microcrystalline) due to high polarity and multiple hydroxyls.
    • Solubility trends: Frequently soluble in polar protic solvents (water, methanol, ethanol) and highly polar aprotic solvents (DMSO, DMF). Solubility can vary widely depending on the aglycone and number of sugar units. A brief solubility screen in water, 50% MeOH/H2O, MeOH, and DMSO is often informative.
    • UV/Vis: Many glycosides lacking extended conjugation exhibit weak UV absorbance above 210–220 nm; lignan-containing congeners may show bands near 275–285 nm (literature, aglycone-dependent).
    • Stability: O‑glycosidic bonds can hydrolyze under strong acid or base and at elevated temperatures; neutral aqueous and alcoholic solutions are generally more stable. Minimize prolonged exposure to strong acids/bases and high heat during handling.

For authoritative, item-specific values, consult the lot-specific CoA/Spec Sheet and SDS.

Quality and Grades
  • Item-specific (Product Data)

    • Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
  • What to expect and how to interpret quality for this item

    • For small-molecule library members and natural products, quality is commonly defined by chromatographic purity (e.g., HPLC/UPLC), identity confirmation (NMR, HRMS/ESI-MS), and, when relevant, water content (KF) and residual solvents. Because no explicit grade is stated for A965995, consult the lot-specific CoA for acceptance criteria, analytical methods, and results.
    • If UV applications (e.g., LC–UV quantitation) are intended, low baseline drift and absence of UV‑active impurities are desirable; check the provided chromatograms on the CoA.
    • If the compound is supplied as an amorphous solid or foam (common for glycosides), slight batch-to-batch variation in physical appearance can occur without affecting purity; rely on analytical data rather than appearance.
  • Stabilizers and additives

    • None are specified for this item. If stabilizers or formulating excipients are present for a given lot, they will be listed on the CoA/Spec Sheet.
  • Recommended user QC (good practice)

    • Upon receipt, verify identity by LC–MS against the reported exact mass and retention time on the CoA.
    • For quantitative work, prepare a fresh calibration standard from a gravimetrically verified stock; document purity correction if the CoA specifies assay <100%.
Reaction and Applications
  • Item-specific (Product Data)

    • Manufacturer Applications: Not specified beyond inclusion in a small-molecule/compound library.
  • Typical research uses for plant glycosides and reference natural products (literature/general; not item-specific claims)

    • Reference standard in phytochemical profiling of Acanthopanax/Eleutherococcus materials by HPLC/UPLC–MS, aiding dereplication and quality control.
    • Analytical method development/validation: calibration curves, recovery studies, and matrix effects evaluation in plant extracts.
    • Chemical stability and hydrolysis studies: kinetic analysis of glycosidic bond cleavage under acid/base or enzymatic conditions.
    • Derivatization for structure elucidation: peracetylation (Ac2O/pyridine) to aid NMR assignment; methylation/silylation for GC–MS when applicable to the aglycone after hydrolysis.
  • Practical tips (general)

    • Protect from strong acids/bases during routine handling to avoid undesired hydrolysis.
    • For LC–MS quantitation, use soft ionization (ESI) and consider ammonium-formate/acetate buffers to promote stable adducts; avoid non-volatile salts.
    • Record solution stability over time at relevant temperatures; many glycosides are more stable in dry solid form than in solution.

These use-cases are general to natural-product glycosides and should be tailored after confirming the exact structure and purity on the CoA for this SKU.

Reaction Conditions

No reaction condition specifications are provided for this item. The following are general, literature-informed conditions relevant to glycoside handling and derivatization; they are NOT specifications for this SKU.

  • Hydrolysis (general)

    • Acidic: Aqueous HCl (0.1–2 M), 60–100 °C, hours to release sugars and aglycone; monitor by LC–MS. Over-hydrolysis can degrade sensitive aglycones.
    • Enzymatic: β‑glucosidase or specific glycosidases, pH 5–6 buffers, 25–40 °C; cleaner selectivity with milder conditions.
  • Peracetylation/benzoylation (derivatization)

    • Acetylation: Ac2O/pyridine or Ac2O/DMAP, 0–25 °C to rt, 1–24 h; quench with MeOH/H2O and purify by column chromatography.
    • Benzoylation: BzCl/pyridine, catalytic DMAP, 0–25 °C; useful to increase UV response and crystallinity.
  • Analytical sample prep

    • LC–MS: Dissolve in MeOH/H2O or DMSO then dilute into aqueous mobile phase with volatile buffers (ammonium acetate/formate, pH 4–7). Filter through 0.22 µm PTFE/NYLON filters.
    • NMR: DMSO‑d6, CD3OD, or D2O (depending on solubility); gentle heating may assist dissolution. Exchangeable OH signals broaden in protic deuterated solvents.
  • Stability guidance (general)

    • Avoid prolonged exposure to strong acids/bases and elevated temperatures. Store solutions at 2–8 °C or −20 °C for extended periods, protecting from light and moisture where feasible.

Always confirm compatibility with the exact structure and functional groups reported on the CoA for this product.

Safety and Handling
  • Item-specific (Product Data)

    • Storage Conditions: Room temperature
    • GHS Classification, Signal Word, Pictograms, H-Statements: Not specified for this item; refer to SDS.
  • General laboratory precautions (not a substitute for the SDS)

    • Handle in a chemical fume hood or well-ventilated area. Avoid inhalation of dust/aerosols and contact with skin/eyes.
    • Recommended PPE: lab coat, safety glasses, and appropriate chemically resistant gloves (e.g., nitrile). For weighing fine powders, consider dust mask/respirator per institutional policy.
    • Avoid incompatibilities typical for organic compounds: strong oxidizers, strong acids/bases (can induce glycosidic hydrolysis), and prolonged high-temperature exposure.
    • Hygiene: Wash hands thoroughly after handling; avoid eating/drinking in work area.
  • First-aid overview (consult the SDS for authoritative guidance)

    • Inhalation: Move to fresh air; seek medical attention if symptoms persist.
    • Skin/eye contact: Rinse with plenty of water for at least 15 minutes; remove contaminated clothing; obtain medical advice as needed.
    • Ingestion: Rinse mouth; seek medical attention per institutional protocol.
  • Spill and disposal

    • Small spills: Avoid dust generation, collect with inert absorbent, and place in suitable container for disposal.
    • Disposal: Follow local regulations for organic laboratory chemicals; do not release to the environment.

Always defer to the product SDS and institutional EHS policies for risk assessment and controls.

Solvent Selection
  • Item-specific (Product Data)

    • No solvent recommendations are specified for this item; refer to CoA/Spec Sheet.
  • General guidance for dissolving glycoside-like natural products (literature-based, not item-specific specs)

    • Start with highly polar solvents: DMSO (anhydrous), methanol, ethanol, or water. Sonication and gentle warming (≤40 °C) can aid dissolution while minimizing hydrolysis risk.
    • For aqueous work, consider co-solvents (e.g., 10–50% MeOH or EtOH in water) to improve solubility while maintaining compatibility with bioassays or chromatographic systems.
    • Avoid strong acidic or basic media during stock preparation unless controlled hydrolysis is intended.
  • Polarity and miscibility (general)

    • Expected high polarity due to multiple hydroxyl groups; typical miscibility with polar protic and some polar aprotic solvents. Limited solubility in nonpolar hydrocarbons.
  • Practical comparison (general)

    • DMSO: Maximum solvating power; suitable for small-volume stock solutions for screening; may complicate certain assays above 1–2% v/v.
    • Methanol/Ethanol: Greener, volatile, LC–MS friendly; good for reference standards and calibration solutions.
    • Water/buffer: Preferred for bioassays if soluble; maintain near-neutral pH to limit degradation.

Document the exact solvent and concentration used for reproducibility, and filter (0.22 µm) solutions intended for LC–MS.

Storage and Reconstitution
  • 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 (good practice; not a specification)

    • Store tightly closed in the original container at ambient temperature in a dry place. Protect from excessive humidity and direct light, especially if the compound contains light‑sensitive chromophores.
    • For long-term retention of analytical integrity, consider secondary containment with desiccant and inert headspace (e.g., nitrogen), even when room-temperature stable.
  • Reconstitution and solution handling (general)

    • Initial dissolution: Use a polar solvent such as methanol, ethanol, water, or DMSO. Sonication and gentle warming (≤40 °C) may aid dissolution.
    • Working solutions: Prepare fresh as needed. If storage is required, aliquot and keep at 2–8 °C (short term) or −20 °C (longer term) in amber vials. Avoid repeated freeze–thaw of a single stock.
    • Compatibility: Avoid strongly acidic or basic media unless conducting controlled hydrolysis. Filter solutions (0.22 µm) before chromatographic use.
  • Stability notes

    • Shelf life and solution stability are lot-dependent and should be confirmed from the CoA. In the absence of item-specific data, verify stability empirically by LC–MS/HPLC over relevant timeframes.

Research Use Note: For research use only.

Structure and Identity

Brief overview: Acanthopanaxoside B is listed in our small-molecule compound library. The catalog entry does not include a full structural definition; use the identifiers below and consult the CoA/Spec Sheet for definitive structure and analytical data.

  • Item-specific (Product Data)

    • Product Name: Acanthopanaxoside B
    • SKU: A965995
    • CAS: 915792-03-9
    • PubChem CID: 11993928
    • InChIKey: 251051 (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/general context (not item-specific specifications)

    • The name “Acanthopanaxoside” is used in the literature for plant-derived glycosides from Acanthopanax/Eleutherococcus (Araliaceae). Members of this family are often glycosylated natural products (e.g., triterpenoid saponins or lignan glycosides). Exact substitution patterns and sugar identities vary among named congeners; do not assume a structure without verifying against the certificate of analysis for this SKU.
  • Structural description (general, conditional)

    • If this item corresponds to a glycoside, typical 2D features would include one or more sugar rings (pyranoses/furanoses) O‑linked to an aglycone (e.g., triterpenoid or lignan core), featuring multiple hydroxyls and acetal linkages. Stereochemistry at sugar centers is typically defined but must be verified for the exact isomer supplied.

Always verify identity with the CoA/Spec Sheet and, if needed, orthogonal methods (NMR, HRMS, LC–MS).

Synthetic Utility
  • Item-specific (Product Data)

    • No synthetic-transformation claims are made for this item beyond its availability as a small-molecule library member.
  • General synthetic perspectives for glycoside-like natural products (literature-based; not item-specific)

    • As standards or substrates in glycosylation/hydrolysis studies: enable benchmarking of enzymatic or acid/base-catalyzed cleavage and re-glycosylation protocols.
    • Derivatization strategies: per-O-acetylation (Ac2O/pyridine or Ac2O/DMAP) to simplify NMR spectra and enhance chromatographic behavior; selective protection/deprotection to map hydroxyl reactivity.
    • Aglycone access: controlled hydrolysis (e.g., aqueous acid under reflux, or enzymatic β-glycosidase) to release the aglycone for further modification or SAR exploration.
    • Retrosynthetic value: native glycosides guide protecting-group strategy and anomeric selectivity considerations in total or semi-synthesis of related targets.
  • Analytical synthetic aids

    • Formation of stable derivatives (e.g., benzoates, acetates) can assist in chiroptical and crystallographic studies when direct crystallization is challenging.

Before undertaking chemical transformations, confirm the exact structure of this SKU from the CoA to choose appropriate protecting groups and reaction conditions.

Target Specificity

This product is a small molecule and not an antibody, enzyme, or targeted biologic; no target specificity data are provided in the Product Data.

  • Item-specific (Product Data)
    • Target, epitope, clone, isotype, species reactivity: Not applicable.

Any biochemical interactions or targets would need to be established experimentally; none are asserted for this catalog item.

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