Cimiside B - ≥97% , CAS No.152685-91-1

CAS: 152685-91-1 Cat. No.: C974691 PubChem CID: 91895424

GRADE & PURITY ≥97%

Storage

Room temperature

Specifications

Specifiche e purezza

≥97%

Condizioni di conservazione di stoccaggio

Room temperature

Purezza

≥97%

Nomi e identificatori

• Sorrisi canonici: CC1CC2C(OC3(C1C4(CCC56CC57CCC(C(C7CCC6C4(C3O)C)(C)C)OC8C(C(C(CO8)O)OC9C(C(C(CO9)O)O)O)O)C)O2)C(C)(C)O
• IUPAC Name: (2S,3R,4S,5R)-2-[(2S,3R,4S,5R)-3,5-dihydroxy-2-[[(1S,2R,3S,4R,7R,9S,12R,14S,17R,18R,19R,21R,22S)-2-hydroxy-22-(2-hydroxypropan-2-yl)-3,8,8,17,19-pentamethyl-23,24-dioxaheptacyclo[19.2.1.01,18.03,17.04,14.07,12.012,14]tetracosan-9-yl]oxy]oxan-4-yl]oxyoxane-3,4,5-triol
• InChIKey: FQXVWSGUAKXSLO-CKLOPMIDSA-N
• INCHI: 1S/C40H64O13/c1-18-14-21-30(35(4,5)47)53-40(52-21)29(18)36(6)12-13-39-17-38(39)11-10-24(34(2,3)22(38)8-9-23(39)37(36,7)33(40)46)50-32-27(45)28(20(42)16-49-32)51-31-26(44)25(43)19(41)15-48-31/h18-33,41-47H,8-17H2,1-7H3/t18-,19-,20-,21-,22+,23+,24+,25+,26-,27-,28+,29-,30+,31+,32+,33-,36-,37-,38-,39+,40+/m1/s1
• Isomeri SMILES: C[C@@H]1C[C@@H]2[C@H](O[C@]3([C@H]1[C@]4(CC[C@@]56C[C@@]57CC[C@@H](C([C@@H]7CC[C@H]6[C@@]4([C@H]3O)C)(C)C)O[C@H]8[C@@H]([C@H]([C@@H](CO8)O)O[C@H]9[C@@H]([C@H]([C@@H](CO9)O)O)O)O)C)O2)C(C)(C)O
• PubChem CID: 91895424
• Termini MeSH: cimigenol-3-O-xylopyranosyl-3-xylpyranoside;cimiside B

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Classe Steroids and steroid derivatives
      • Subclass Steroidal glycosides
        • Level5 Steroidal saponins
          • Level6 Cucurbitacin glycosides

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Classe: Steroids and steroid derivatives
• Subclass: Steroidal glycosides
• Intermediate Tree Nodes: Steroidal saponins
• Direct Parent: Cucurbitacin glycosides
• Alternative Parents: Triterpenoids Cycloartanols and derivatives Hydroxysteroids O-glycosyl compounds Disaccharides Oxepanes Ketals Oxanes Tertiary alcohols 1,3-dioxolanes Secondary alcohols Cyclic alcohols and derivatives Polyols Oxacyclic compounds Hydrocarbon derivatives
• Molecular Framework: Aliphatic heteropolycyclic compounds
• Substituents: Cucurbitacin glycoside skeleton - Cycloartanol-skeleton - 9b,19-cyclo-lanostane-skeleton - Cycloartane-skeleton - Triterpenoid - 15-hydroxysteroid - Hydroxysteroid - Disaccharide - Glycosyl compound - O-glycosyl compound - Ketal - Oxepane - Oxane - Tertiary alcohol - Meta-dioxolane - Cyclic alcohol - Secondary alcohol - Organoheterocyclic compound - Acetal - Oxacycle - Polyol - Organooxygen compound - Alcohol - Hydrocarbon derivative - Organic oxygen compound - Aliphatic heteropolycyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as cucurbitacin glycosides. These are polycyclic compounds containing a carbohydrate derivative glycosidically linked to a curcubitane nucleus.
• 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: 752.900 g/mol
• XLogP3: 2.200
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 13
• Rotatable Bond Count: 5
• Exact Mass: 752.435 Da
• Monoisotopic Mass: 752.435 Da
• Topological Polar Surface Area: 197.000 Ų
• Heavy Atom Count: 53
• Formal Charge: 0
• Complexity: 1460.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 21
• 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 tested application protocols are provided for this SKU.

• Item-specific note:

  • Assay types and recommended dilutions: Not specified for this item; refer to CoA/Spec Sheet.

• General guidance for small-molecule library use (non-binding suggestions):

  • Stock preparation: dissolve in anhydrous DMSO to a convenient concentration (e.g., 10–50 mM), vortex and, if needed, sonicate briefly. Filter (0.2 µm PTFE) for analytical work.
  • Plate handling: dispense into assay plates using low-retention tips; minimize freeze–thaw cycles by aliquoting.
  • Aqueous dosing: dilute into buffer with immediate mixing to minimize precipitation; include appropriate vehicle controls.
  • Analytical QC: confirm identity and purity by LC-MS and 1H NMR when establishing a new lot for screening.

For any validated, application-specific protocol, consult internal SOPs or develop method conditions empirically with small-scale trials.

Biological Roles

Literature/class-level context: Cimiside-type compounds are reported constituents of Cimicifuga (Actaea) species, commonly categorized as triterpenoid glycosides (saponins).

• Putative biological roles in plants (general):

  • Defense-related secondary metabolites with surfactant properties that can disrupt cell membranes of herbivores and pathogens.
  • Possible roles in plant–microbe interactions and stress responses; storage forms for modified triterpenes with improved transport/compartmentalization.

• Biochemical properties (class-level):

  • Amphiphilic architecture (hydrophobic triterpene + hydrophilic sugar) enables micelle formation in aqueous environments at sufficient concentrations.
  • Interactions with lipid bilayers, proteins, and membranes are commonly reported for saponins; specific activities vary widely with aglycone structure and glycosylation pattern.

• Research relevance:

  • Serve as chemotaxonomic markers in Actaea/Cimicifuga phytochemistry.
  • Useful as analytical standards when characterizing botanical extracts by LC-MS/MS, enabling targeted quantitation in metabolomics workflows.

• Important caveats:

  • No item-specific biological activity, potency, or target data are provided here. Any biological statements above are general to the class and should not be construed as claims for this specific lot or compound in therapeutic, diagnostic, or clinical contexts.

For precise biological data on Cimiside B, consult primary literature sources and confirm experimentally under your specific assay conditions.

Buffer Applications

Cimiside B is not a buffering agent and is not typically used to control solution pH. Consequently, standard buffer formulation guidance (e.g., phosphate, Tris, HEPES) does not directly apply.

• Practical notes for assay buffers (general handling of saponins/natural products):
  • When dosing into aqueous buffers, pre-dissolve in DMSO or ethanol and add slowly with vigorous mixing to avoid precipitation; maintain final organic co-solvent at minimal levels compatible with your assay (often ≤1–2%).
  • Consider inclusion of non-ionic surfactants at low levels if colloidal aggregation is a concern in biochemical screens, and confirm effects on assay performance.

If a buffer recipe is required for your workflow, select based on target pH and compatibility with your detection method; Cimiside B does not impose a specific buffer choice.

Green Alternatives

Because Cimiside B is a solid natural product used primarily as a reference standard or screening compound, greener practice focuses on solvent choice and minimization of hazardous reagents.

• Greener solvent substitutions (general guidance):

  • Replace acetonitrile with ethanol or water–ethanol blends where chromatographic resolution allows (note: saponins often separate well on water–MeOH systems).
  • Prefer ethanol over methanol for preparative work due to lower toxicity, when solubility and performance are acceptable.
  • Use 2-propanol as a stronger, greener modifier in RP-HPLC gradients to reduce ACN usage; verify detector compatibility (ELSD/CAD).

• Minimizing derivatization hazards:

  • When acetylation is necessary, consider catalytic DMAP in acetic anhydride under solvent-free or minimal-solvent conditions; quench and neutralize responsibly. Alternatively, use greener acyl donors (e.g., isopropenyl acetate) with enzymatic catalysis (literature) when feasible.

• Process considerations:

  • Implement microscale workflows to cut solvent volume for method development.
  • Opt for aqueous buffer systems with small percentages of bio-based co-solvents (ethanol, glycerol) for assay dilutions.

• Comparison (illustrative):

  • Conventional: ACN-rich gradients, methanol sample prep, chlorinated solvents for workup.
  • Greener: water–EtOH or water–IPA gradients, EtOH/DMSO sample prep, complete avoidance of chlorinated solvents.

Trade-offs: greener solvents may alter retention/selectivity and detector backgrounds; perform small-scale scouting runs to balance sustainability with analytical performance.

Pharmaceutical Uses

No pharmaceutical or clinical uses are specified for this item. This product is supplied strictly for research and laboratory use.

• Research/formulation context (general):

  • Natural product reference compounds like Cimiside B may be used as analytical standards for quality control of botanical raw materials and extracts (non-clinical). Such uses involve validated chromatographic methods and appropriate reference controls.
  • Preformulation screening can assess solubility, stability, and compatibility with excipients, but any outcomes are for research only and not for human administration.

• Pharmacopeial status:

  • No pharmacopeial monograph is indicated for this item. If a compendial reference exists for a related standard, consult that document separately.

• Excipients and dosage forms:

  • Not applicable; no excipient role is specified or implied for this compound.

Always adhere to institutional policies for handling research chemicals and do not incorporate this material into products intended for clinical or diagnostic use.

Physical Properties

• Item-specific specifications:

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

• Storage conditions (from Product Data):

  • Store at room temperature.

• Literature/class-level properties for triterpenoid glycosides (for context only; not item specifications):

  • Physical state: typically off-white to pale solids or amorphous powders.
  • Solubility: sparingly soluble in water alone; soluble in polar organic solvents (MeOH, EtOH) and in DMSO; aqueous solubility can improve with co-solvents or cyclodextrin complexation.
  • UV characteristics: often exhibit weak UV absorption above 210–220 nm due to lack of strong chromophores; detection by ELSD, CAD, or derivatization is common in HPLC analyses.
  • LogP/logD: aglycones are lipophilic; glycosylation increases polarity, yielding moderate apparent logD in aqueous-organic systems (value varies with sugar number and pH; literature, class-level).
  • Melting behavior: many saponins show broad decomposition rather than sharp melting; reported melting points, when available, vary widely and may reflect hydrates/solvates (literature).

• Practical notes:

  • Prepare analytical stocks in dry DMSO or MeOH for LC-MS/NMR. For aqueous assays, use serial dilution into buffer containing 1–5% co-solvent and gentle warming/sonication to minimize precipitation.

All numerical values not explicitly listed above are not specified for this item; refer to CoA/Spec Sheet for definitive specifications.

Quality and Grades

• Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.

• Interpreting typical grades (general guidance):

  • Research-grade natural products are commonly provided at high chemical purity suitable for analytical characterization (e.g., NMR/LC-MS) and biochemical screening. When labeled as HPLC-grade or ≥95% by HPLC/NMR, this indicates low levels of organic impurities and is appropriate for screening assays and as analytical standards.
  • For compound libraries, purity is frequently measured by LC-UV/CAD/ELSD plus MS. Note that saponins may lack strong chromophores; alternative detection (ELSD/CAD) is often used in purity assessment.

• Stabilizers/additives:

  • No stabilizers are listed for this item. If stabilizers or counter-ions are present (e.g., formate/acetate), they will be disclosed on the CoA/Spec Sheet.

• What to check on receipt:

  • Verify lot-specific purity, water content, and identity (LC-MS, 1H/13C NMR) as needed for your application. For bioassays, confirm absence of residual extraction solvents and assess solubility in your assay vehicle.

• Documentation:

  • For definitive grade, purity, and analytical data (chromatogram, spectra), consult the lot-specific Certificate of Analysis (CoA) or Specification Sheet.

Reaction and Applications

This listing is positioned for small-molecule/compound library use. While no manufacturer applications are provided for this SKU, Cimiside B, as a triterpenoid glycoside, supports several research workflows (literature/class-level):

• Bioassay screening:

  • Natural product hit-finding, phenotypic assays, and target-agnostic profiling. Prepare DMSO stocks and ensure colloid/aggregation controls (e.g., 0.01% Triton X-100 or BSA) where appropriate.

• Analytical reference standard:

  • Method development and QC for botanical materials (e.g., Cimicifuga/Actaea). Employ RP-HPLC or UHPLC with ELSD/CAD or MS detection; validate linearity, LOD/LOQ, and recovery with spiked matrices.

• Derivatization chemistry (on the bench):

  • Acylation/acetylation of hydroxyl groups using Ac2O/pyridine or Ac2O/DMAP to generate peracetates for structure elucidation (NMR signal dispersion) or stability studies.
  • Selective silylation (e.g., TMS/ TBDMS) to aid GC-MS of aglycones after hydrolysis.
  • Acid/base-catalyzed hydrolysis of glycosidic linkages to access the aglycone for comparative analysis.

• Isolation/purification workflows:

  • Solid-phase extraction (SPE) and semi-preparative RP-HPLC using water–MeOH/ACN gradients; collect ELSD-positive fractions.

• Practical tips:

  • Avoid strong mineral acids/bases or elevated temperatures if structural integrity must be retained. For stability, minimize aqueous exposure at high pH. Use amber vials and desiccation to limit hydrolytic/oxidative changes.

All applications are for research and analytical purposes only.

Reaction Conditions

No item-specific reaction conditions are provided. The following are literature/class-level guidelines for common manipulations of triterpenoid glycosides and may be adapted for Cimiside B with appropriate controls:

• Peracetylation of hydroxyl groups:

  • Reagents: acetic anhydride, catalytic DMAP or pyridine base.
  • Solvent: pyridine or dichloromethane (DCM); greener alternatives include neat Ac2O with catalytic DMAP.
  • Temperature/time: 0–25 °C, 1–24 h, monitor by TLC/LC-MS.

• Selective silylation:

  • Reagents: TBDMS-Cl with imidazole (DMF) or TMS-Cl with base.
  • Conditions: anhydrous, 0–25 °C; quench and purify by RP-HPLC if needed.

• Acid-catalyzed deglycosylation (to aglycone):

  • Reagents: dilute mineral acid (e.g., 0.1–1 M HCl) or TFA in aqueous MeOH.
  • Temperature/time: 40–80 °C, 0.5–6 h; excessive conditions risk aglycone degradation.

• Enzymatic hydrolysis (milder):

  • Glycosidases tailored to sugar/linkage; aqueous buffer pH 4–6, 25–40 °C, hours to days.

• Purification/analysis:

  • RP-HPLC on C18 with water–MeOH/ACN gradients; detect by ELSD/CAD/MS. Volatile buffers (e.g., formic acid/ammonium formate) aid MS compatibility.

• Expected outcomes:

  • Yields and selectivity are substrate- and site-dependent; verify by LC-MS/NMR at each step. No yield claims are made for this specific item.

Always conduct small-scale trials first and optimize to your laboratory’s safety and waste-handling standards.

Safety and Handling

• Regulatory note: For research use only. Not for human or veterinary use.

• GHS classification and hazard statements (item-specific):

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

• General laboratory precautions (good practice for natural products):

  • Wear appropriate PPE: lab coat, safety glasses, and chemical-resistant gloves (e.g., nitrile). Handle powders in a fume hood to avoid inhalation of dust/aerosols.
  • Avoid ingestion, inhalation, or skin contact. Wash thoroughly after handling. Decontaminate surfaces after weighing.
  • Incompatibilities: strong oxidizers and strong acids/bases may degrade glycosidic linkages and hydroxyl-bearing terpenoids; avoid prolonged exposure to elevated temperatures and moisture which can promote hydrolysis.
  • First aid (overview; defer to SDS): in case of skin or eye contact, rinse with water for at least 15 minutes; if inhaled, move to fresh air; if swallowed, rinse mouth. Seek medical attention if symptoms persist.

• Stability considerations:

  • Glycosidic natural products can undergo hydrolysis in strongly acidic/basic media and may slowly degrade with prolonged exposure to moisture and heat. Store tightly closed, protect from excessive humidity and light when feasible.

Consult the product SDS for authoritative and complete safety, toxicity, and disposal guidance.

Solvent Selection

Cimiside B is best handled as a polar natural product standard. While item-specific solubility data are not provided, class-level behavior of triterpenoid glycosides guides solvent choice.

• Primary stock solvents (literature/class-level):

  • DMSO: typically excellent for preparing concentrated stocks (e.g., 10–50 mM for screening), with good stability and compatibility with aqueous dilution.
  • Methanol or Ethanol: good solubility; suitable for analytical sample prep (HPLC, LC-MS). For bioassays, limit final alcohol to ≤1–2% v/v.
  • Water/co-solvent systems: limited solubility in pure water; addition of 1–5% DMSO, gentle heating, or cyclodextrin can improve dissolution.

• Miscibility and polarity notes (general):

  • As glycosylated triterpenes carry multiple hydroxyls and sugars, they have intermediate polarity: more polar than aglycones, less than small saccharides. This favors polar aprotic/protic organic media.

• Practical selection tips:

  • For HTS: prepare a DMSO master stock, then dilute into assay buffer with vigorous mixing to avoid precipitation.
  • For NMR: MeOD-d4, DMSO-d6, or Pyridine-d5 are common; addition of a trace of TFA-d1 can sharpen sugar signals but may promote slow hydrolysis—use judiciously.
  • For purification: reverse-phase (C18) with water–acetonitrile or water–methanol gradients is typical; detect by ELSD/CAD.

• Comparison (general):

  • DMSO: highest solvating power; viscous, hygroscopic.
  • MeOH/EtOH: greener, volatile; may better suit preparative work.
  • Acetonitrile: good for RP-HPLC mobile phases; variable solubility for saponins.

Storage and Reconstitution

• Storage (from Product Data):

  • Store at room temperature.

• Item-specific details:

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

• General recommendations for triterpenoid glycosides:

  • Keep container tightly closed in a dry, well-ventilated place. Protect from prolonged exposure to humidity and direct light. Use desiccant if available.
  • For long-term archiving or sensitive assays, consider storing aliquots at 2–8 °C or −20 °C desiccated to minimize hydrolysis; allow to equilibrate to room temperature before opening to prevent condensation.

• Reconstitution guidelines (general):

  • Prepare a concentrated stock in dry DMSO or methanol. Typical working approach is to make 10–50 mM DMSO stocks, then dilute into assay buffer to the desired final concentration, keeping final DMSO low (commonly ≤1–2% v/v).
  • If aqueous solubility is limited, employ co-solvent strategies (DMSO or ethanol 1–5%), gentle warming (≤40 °C), and/or sonication. Confirm clarity visually and by light scattering where critical.

• Freeze–thaw:

  • Minimize by aliquoting stocks. Avoid repeated freeze–thaw cycles that can promote precipitation or degradation.

Refer to the product’s CoA/Spec Sheet and SDS for any lot-specific storage instructions or incompatibilities.

Structure and Identity

Brief description: Cimiside B is a plant-derived small molecule natural product, commonly classified among triterpenoid glycosides (saponins) isolated from Cimicifuga (Actaea) species (literature). It is supplied here as a research-use chemical in a small-molecule library context.

• Item-specific (from Product Data):

  • SKU: C974691
  • Product Name: Cimiside B
  • CAS: 152685-91-1
  • InChIKey: 89892 (as provided; note this is shorter than typical InChIKeys)
  • 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 (literature/general):

  • Likely a cycloartane-type triterpene aglycone bearing one or more glycosidic sugar residues (typical for Cimiside-type constituents from Cimicifuga/Actaea).
  • Functional groups commonly include: multiple secondary/tertiary alcohols on a polycyclic triterpene scaffold, glycosidic ether linkages, and possibly ester or acyl substituents depending on the exact congener.
  • Stereochemistry: densely stereogenic (polycyclic steroid-like framework and defined sugar stereochemistry), with multiple axial/equatorial orientations in the ring system (literature, class-level description).

• 2D structural description (literature/class-level): a fused tetracyclic triterpene core (steroid-like) attached at C-3 (commonly) to a mono- or oligosaccharide via a β-glycosidic linkage; additional hydroxyls and side-chain modifications may be present.

Note: Definitive structure identifiers (canonical SMILES/InChI) and exact substituent pattern for this catalog item are not specified here; consult the product CoA/Spec Sheet or primary literature for exact constitutional and stereochemical assignment.

Synthetic Utility

While Cimiside B is a complex natural product rather than a routine building block, it offers utility in synthetic and analytical chemistry (literature/class-level):

• Functional group landscape:

  • Multiple secondary/tertiary alcohols on a triterpene core and glycosidic hydroxyls provide handles for selective protection, acylation, and oxidation. Ether (glycosidic) linkages enable hydrolysis/enzymatic transformations.

• Typical transformations:

  • Peracetylation or selective acylation to simplify NMR analysis and facilitate crystallization for X-ray studies.
  • Controlled acid-catalyzed hydrolysis to remove sugars, yielding the aglycone for SAR comparisons.
  • Silyl protection (TBDMS/TMS) of alcohols to enable derivatization or differential reactivity across the scaffold.
  • Periodate-mediated oxidative cleavage can interrogate sugar identity/linkage (applies to vicinal diols in certain monosaccharides).

• Retrosynthetic/analytical applications:

  • Serves as a standard in dereplication workflows: accurate mass and characteristic fragment ions (sugar losses) in MS/MS aid rapid identification of related congeners in plant extracts.

• Cautions:

  • Strong acids/bases and elevated temperatures can induce decomposition, rearrangement, or deglycosylation. Reaction planning should account for dense stereochemistry and neighboring group effects within sugars.

These utilities are general to triterpenoid glycosides; confirm conditions empirically for Cimiside B and consult the CoA for any lot-specific constraints.

Target Specificity

No target, binding, or biological specificity data are provided for this item.

• Item-specific statement:

  • Target specificity: Not specified for this item; refer to CoA/Spec Sheet and primary literature if available.

• Context (general):

  • Triterpenoid glycosides can interact with membranes and proteins in a non-specific or multi-target manner; any specific target claims must be established experimentally for each congener and are not inferred here.

This product is offered for research use only, without implied biological target or mechanism.