Ptaquiloside , CAS No.87625-62-5

CAS: 87625-62-5 Cat. No.: P1016814 PubChem CID: 13962857

Storage

Room temperature

Specifications

Condizioni di conservazione di stoccaggio

Room temperature

Nomi e identificatori

• Sorrisi canonici: CC1CC2(C=C(C3(CC3)C(C2C1=O)(C)O)C)OC4C(C(C(C(O4)CO)O)O)O
• IUPAC Name: (2R,3aR,7S,7aR)-7-hydroxy-2,5,7-trimethyl-3a-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyspiro[3,7a-dihydro-2H-indene-6,1'-cyclopropane]-1-one
• InChIKey: GPHSJPVUEZFIDE-YVPLJZHISA-N
• INCHI: 1S/C20H30O8/c1-9-6-20(28-17-15(25)14(24)13(23)11(8-21)27-17)7-10(2)19(4-5-19)18(3,26)16(20)12(9)22/h7,9,11,13-17,21,23-26H,4-6,8H2,1-3H3/t9-,11-,13-,14+,15-,16-,17+,18+,20-/m1/s1
• Isomeri SMILES: C[C@@H]1C[C@]2(C=C(C3(CC3)[C@@]([C@H]2C1=O)(C)O)C)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O
• CAS alternativo: 87625-62-5
• PubChem CID: 13962857
• Termini MeSH: aquilide A;braxin C;ptaquiloside

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 Oxanes Tertiary alcohols Secondary alcohols Ketones Polyols Oxacyclic compounds Acetals Primary alcohols Organic oxides Hydrocarbon derivatives Aldehydes
• Molecular Framework: Aliphatic heteropolycyclic compounds
• Substituents: Hexose monosaccharide - O-glycosyl compound - Monosaccharide - Oxane - Tertiary alcohol - Secondary alcohol - Ketone - Polyol - Organoheterocyclic compound - Oxacycle - Acetal - Primary alcohol - Hydrocarbon derivative - Organic oxide - Carbonyl group - Aldehyde - Alcohol - Aliphatic heteropolycyclic compound
• Descrizione: 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

Proprietà chimiche e fisiche

• Peso molecolare: 398.400 g/mol
• XLogP3: -1.300
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 3
• Exact Mass: 398.194 Da
• Monoisotopic Mass: 398.194 Da
• Topological Polar Surface Area: 137.000 Ų
• Heavy Atom Count: 28
• Formal Charge: 0
• Complexity: 702.000
• 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

No assay-validated protocols are provided for this specific catalog item. Common research uses (literature-informed) include:

• Preparation of analytical standards for LC–MS/MS: Weigh under low humidity, dissolve in water, methanol, or water–acetonitrile with 0.1% formic acid, and prepare calibration curves with matrix-matched standards as needed. Validate stability over the analytical window.
• Stability/degradation studies: Incubate at defined pH and temperature; sample at intervals; quench and analyze by LC–MS to quantify parent vs. degradation products.

Item-specific parameters such as recommended stock concentrations, diluents, or validated matrices are Not specified for this item; refer to CoA/Spec Sheet. Adapt conditions to your internal SOPs and regulatory framework.

Biological Roles

Ptaquiloside is a defensive natural product produced by bracken ferns (Pteridium spp.). The following points summarize general, literature-based biological context; they are not medical or clinical claims.

• Ecological function: Acts as a chemical defense against herbivory and microbial attack. Its chemically reactive illudane core can form electrophilic species that react with biomolecular nucleophiles, contributing to deterrence (literature).
• Biosynthesis: Derived from sesquiterpene pathways, yielding an illudane-type skeleton that is subsequently glycosylated to increase transport and storage in plant tissues.
• Distribution: Reported in various tissues of bracken fern, with levels influenced by developmental stage and environmental conditions (literature). It can leach into soils and water, motivating environmental monitoring studies.
• Stability in biological systems: Under physiological to alkaline pH, ptaquiloside can degrade to pterosin-type compounds; in biological matrices, pH and enzymatic activity modulate this conversion. Glycosidases may hydrolyze the sugar, altering reactivity and mobility (literature).
• Analytical biomonitoring: Employed as a target analyte in studies of feed, milk, and water to understand exposure pathways in agro-ecological settings; standards are used to calibrate LC–MS methods.

For use in research assays, handle with care and design protocols that control pH and time to capture relevant species (parent vs. degradation products) based on your biological question.

Buffer Applications

This compound is not a buffering agent and is not typically used to formulate laboratory buffers. If your work involves stability or analytical studies, buffers may be used to control pH during handling:

• General guidance (literature): mildly acidic aqueous buffers (e.g., acetate or formate at pH ~4–6) can reduce base-catalyzed degradation during sample preparation and LC analysis. Avoid strong bases or prolonged exposure to high pH which accelerates conversion to pterosin-type products.

For precise buffer recipes or pH-stability curves, consult method-development literature and validate conditions for your assay.

Green Alternatives

This product is a specialized natural product standard, not a commodity solvent or bulk reagent. “Greener alternative” considerations focus on analytical workflows and sample preparation rather than replacing the molecule itself.

Greener workflow suggestions (general):

• Solvent selection: Favor water-rich mobile phases and minimize acetonitrile by using gradient methods optimized for retention on polar stationary phases (e.g., HILIC) when compatible with analyte stability.
• Acid modifiers: Use volatile, low-toxicity acids (formic or acetic acid) at the lowest effective concentration to stabilize during analysis and maintain MS compatibility.
• Sample cleanup: Employ micro-scale SPE or QuEChERS-type protocols to reduce solvent volume and waste compared with large-scale liquid–liquid extraction.
• Energy: Conduct extractions and analyses at ambient temperature where possible; avoid prolonged heating that also accelerates degradation.

Illustrative comparison (workflow-level; literature-based):

• Aqueous MeOH (50–70%) vs neat organic: similar recoveries with reduced organic solvent usage; maintain mildly acidic pH to improve stability.
• Miniaturized LC (UHPLC, microbore columns): less solvent per run; improved sensitivity can allow lower standard concentrations and less material consumption.

Trade-offs:

• Strongly aqueous conditions may affect retention on reversed-phase columns; consider HILIC or embedded polar phases.
• Acidified media enhance stability but may hydrolyze glycosides if too strong/long; optimize conditions to balance stability and integrity.

Pharmaceutical Uses

This item is not an excipient and is not used in pharmaceutical formulation practice. It is provided strictly for research use only.

Relevant research/formulation-adjacent notes (general, non-clinical):

• Analytical reference: May be employed as a reference standard in studies assessing removal or presence of plant-derived toxins in process streams, water, or food-related matrices using LC–MS.
• Stability studies: Investigations into pH-driven degradation pathways can inform risk assessments for botanical materials; these are research activities, not pharmaceutical uses.

Research Use Note: For research use only. Not for human or veterinary use.

Physical Properties

Item-specific numerical specifications are not provided for this catalog entry. Consult the CoA/Spec Sheet for definitive values relevant to your lot.

Available item-specific values:

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

General/literature characterization (for context; not item specifications):

• Ptaquiloside is a polar, carbohydrate-bearing natural product typically encountered as a solid and readily soluble in water and polar protic/aqueous-organic media due to the glucose residue.
• The aglycone contains acid/base-labile functionalities. Ptaquiloside is known to undergo base-catalyzed ring opening/elimination to form pterosin-type products; thus it is chemically unstable under alkaline conditions (literature).
• Thermal sensitivity is reported; prolonged heating accelerates degradation (literature). Dry, cool handling is typically recommended for analytics, though follow the item’s stated storage conditions.
• Partitioning: expected to have low logP relative to non-glycosylated sesquiterpenes (literature qualitative assessment).

If you require precise values such as melting point, aqueous solubility at defined pH, or extinction coefficients for quantitative assays, please request the current CoA or product specification sheet.

Quality and Grades

Item-specific grade and purity are not listed in the provided data.

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

Guidance on interpreting grades for this compound class (general):

• Analytical/Reference standard grade: Emphasizes identity confirmation (1H/13C NMR, HRMS), tight purity specification by quantitative methods (HPLC with ELSD/UV), and defined water/residual solvent content. Suitable for quantitative method development and environmental/food-chain residue analysis.
• Research grade: Fit for discovery and mechanistic studies. May have broader limits on minor related substances (e.g., co-occurring pterosins). For sensitive bioassays or toxicology mechanisms, consider stricter purity.

Stabilizers and implications:

• Stabilizers are sometimes avoided to prevent matrix complications in quantitative analysis. If present, they must be disclosed on the CoA. For base-labile compounds, packaging under inert atmosphere or inclusion of weakly acidic microenvironment (e.g., acidic desiccant) may be used; check your item’s documentation.

What is specific to this item:

• Where numerical specifications (e.g., UV cutoff, residual metals, water, specific related substances) are critical, they are Not specified for this item; refer to CoA/Spec Sheet. Contact Aladdin Scientific support with your SKU (P1016814) for detailed release criteria.

Reaction and Applications

This compound is primarily used as a research analyte/standard and mechanistic probe rather than as a general-purpose reagent. Key application areas (literature):

• Mechanistic toxicology: Ptaquiloside serves as a model illudane-type electrophile precursor. Under basic or nucleophilic conditions it can generate reactive intermediates that alkylate nucleophiles; researchers study kinetics, adduct profiles, and decomposition pathways.
• Environmental/food-chain analytics: Used as a reference standard for quantifying contamination in water, milk, forage, and plant materials (method validation for LC–MS/MS and HILIC/RP-HPLC).
• Natural products chemistry: Benchmark for isolation, stability studies, and transformation to pterosins. Employed to elucidate structure–reactivity relationships of cyclopropyl-containing sesquiterpene glycosides.

Practical tips (general):

• Handle under mildly acidic conditions (e.g., 0.05–0.1% formic/acetic acid) during sample prep to suppress base-catalyzed degradation; avoid strong acids that may hydrolyze the glycosidic bond.
• Prepare fresh stock solutions when possible; for longer studies, aliquot and minimize freeze–thaw cycles as appropriate for your protocol.
• For derivatization or stability studies, carefully control pH, temperature, and time; monitor by LC–MS or HPLC–UV/ELSD.

Note: The above are literature-informed application scenarios and not manufacturing specifications for this item. Consult the product’s CoA/SDS and your validated SOPs for operational details.

Reaction Conditions

Ptaquiloside is more often the subject of degradation and transformation studies than a reagent. Typical literature conditions are summarized for reference only (not product specifications):

• Base-catalyzed conversion to pterosins: Mildly to strongly basic aqueous conditions (e.g., carbonate/bicarbonate buffers or dilute hydroxide) at ambient temperature promote elimination/ring opening to pterosin-type products. Reaction times vary from minutes to hours depending on pH, temperature, and solvent composition. Monitor by LC–MS.
• Acid-catalyzed hydrolysis: Dilute mineral or organic acids (e.g., 0.01–0.1 M HCl or formic acid) may hydrolyze the glycosidic bond and/or induce rearrangements over longer times. Excessively strong acid can cause complex decomposition.
• Enzymatic hydrolysis: β-Glucosidases can cleave the glycoside under buffered aqueous conditions (pH ~5) at 25–37 °C, liberating the aglycone; kinetics depend on enzyme source and loading.
• Solvent systems: Water, aqueous alcohols, and water–acetonitrile mixtures are common media; inclusion of volatile acids (formic/acetic) can improve stability during analysis yet may influence reaction pathways.

Practical notes:

• Control pH precisely; small changes markedly affect rate and product distribution.
• Minimize headspace oxygen/light if radical or oxidative side-reactions are a concern; however, primary pathways are pH-driven.
• Quench samples rapidly (cooling, acidification) and analyze promptly to avoid post-quench transformations.

Always validate with small-scale trials and analytical tracking before committing valuable samples.

Safety and Handling

Authoritative safety guidance must come from the SDS for your specific lot. The following are general laboratory precautions for handling reactive glycosidic natural products like ptaquiloside.

Item-specific hazard data:

• GHS classification: Not specified for this item; refer to SDS.
• Signal word / H-statements / Pictograms: Not specified for this item; refer to SDS.

General precautions (literature-informed and good laboratory practice):

• Potential hazards: Ptaquiloside and related illudane glycosides are chemically reactive and can alkylate nucleophiles under certain conditions (literature). Treat as toxic; avoid inhalation, ingestion, and skin contact.
• Engineering controls: Work in a certified chemical fume hood. Avoid aerosolization and dust generation.
• PPE: Lab coat, safety glasses, and appropriate chemical-resistant gloves (e.g., nitrile). Consider double-gloving for extended handling.
• Incompatibilities: Strong bases (accelerate degradation and may form reactive intermediates), strong acids (hydrolysis of glycoside), strong oxidizers. Avoid prolonged exposure to heat and light.
• First aid (overview; defer to SDS): If skin contact occurs, wash with soap and water. If eye exposure, rinse cautiously with water for several minutes; remove contacts if present and easy to do. If inhaled, move to fresh air. If ingested, rinse mouth; seek medical attention in all cases of exposure.
• Waste: Collect contaminated disposables/solutions as hazardous chemical waste. Decontaminate surfaces with appropriate solvent and detergent; avoid strong base that could induce reactive degradation products.

Always consult and follow the SDS and institutional EHS policies.

Solvent Selection

Ptaquiloside is a polar glycoside; solvent choice should balance solubility with chemical stability.

General/literature guidance (not item specifications):

• Polarity/miscibility: High affinity for water and polar protic solvents (water, methanol, ethanol). Also soluble in mixed aqueous-organic media (e.g., water–acetonitrile) used in HPLC.
• Stability considerations: Avoid basic media (pH > ~8–9) that promote degradation to pterosin-type products. Mildly acidic aqueous buffers can enhance stability during sample prep and chromatography.
• Typical use scenarios:
  • Analytical standards: Dissolve in water, methanol, or water–acetonitrile with 0.1% acid (e.g., formic acid) for LC–MS; store aliquots cold and protected from light if your method requires extended stability.
  • Extraction from matrices: Solid-phase extraction or aqueous extraction followed by cleanup under mildly acidic conditions is common.

Comparison (literature-based):

• Water: maximal solubility; may need acidification for stability.
• Methanol/EtOH: excellent solubility; convenient for stock solutions; monitor for transacetalization under strongly acidic conditions.
• Acetonitrile: used in LC; typically as mixed aqueous system; limited buffering capacity but good for MS compatibility.

For preparative work, pre-screen pH and solvent to minimize degradation. Always validate recovery and stability in your exact matrix and solvent system.

Storage and Reconstitution

Follow the product label and CoA for definitive guidance.

Item-specific instructions:

• Storage Conditions: Room temperature (per product data).
• Shipped In: Not specified for this item; refer to CoA/Spec Sheet.

General handling guidance (literature-informed; not item specifications):

• Protect from moisture, strong light, and elevated temperatures to minimize degradation. If long-term storage is planned, consider secondary containment with desiccant.
• For solution stocks, choose solvents compatible with your assay (e.g., water, methanol, or water–acetonitrile) and consider mild acidification (e.g., 0.05–0.1% formic/acetic acid) to suppress base-catalyzed degradation. Prepare single-use aliquots to avoid repeated opening.
• Freeze–thaw: If solutions are stored at reduced temperature, avoid multiple freeze–thaw cycles; thaw on ice and use promptly.
• Compatibility: Avoid storing solutions in basic media or with reactive nucleophiles; glass vials with PTFE-lined caps are preferred for analytical stocks.

Reconstitution: If supplied as a solid, dissolve with gentle mixing in a small volume of a suitable solvent; confirm concentration by weight/volume and, if critical, by quantitative HPLC. Because item-specific solubility and concentration limits are Not specified for this item; refer to CoA/Spec Sheet, verify suitability in a small-scale test before preparing bulk stocks.

Structure and Identity

Ptaquiloside is a naturally occurring norsesquiterpene glycoside isolated from bracken ferns (Pteridium spp.), featuring a highly strained cyclopropyl-containing illudane skeleton glycosylated to a carbohydrate (glucose) moiety.

• CAS: 87625-62-5
• PubChem CID: 13962857 (literature identifier)
• InChIKey: 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 description):

• Contains an illudane-type tricyclic core incorporating a strained cyclopropane ring adjacent to an enol ether/lactone functionality.
• β-D-glucopyranoside linkage at a secondary alcohol of the aglycone; the sugar increases polarity and aqueous solubility.
• Multiple oxygenated centers (hemiacetal/acetals and glycosidic linkage) confer sensitivity to acid/base and hydrolysis.
• Stereochemistry: multiple chiral centers in both aglycone and sugar; naturally occurring as a single diastereomer (literature).

2D structure in words:

• A fused bicyclic carbocycle bearing a three-membered ring, connected to an enol-lactone-like fragment; one of the ring carbons bears an O-glycosidic tether to a six-membered glucose ring in chair conformation with axial/equatorial substituents consistent with β-linkage.

Synthetic Utility

Ptaquiloside itself is not commonly used as a building block in synthesis due to its complexity and lability; however, it has value in the following synthetic and analytical contexts (literature):

• Reaction probe: Serves as a substrate to study solvolysis, glycosidic hydrolysis, and base-catalyzed ring opening of illudane sesquiterpenes, furnishing pterosin derivatives. Useful for mapping mechanisms of cyclopropane ring opening and rearrangements.
• Calibration and validation: Employed to validate derivatization protocols targeting reactive enol-lactone/enol-ether motifs and to benchmark stability-indicating analytical methods.
• Transformation to aglycone/pterosins: Controlled hydrolysis or base treatment generates characteristic products (e.g., pterosin B-type structures) that can be isolated or detected for structural studies.

Functional group reactivity overview (general):

• Glycosidic linkage: acid/base-labile; susceptible to enzymatic hydrolysis.
• Enol-lactone/enol-ether motif: undergoes nucleophilic addition/elimination; base accelerates formation of electrophilic intermediates.
• Cyclopropyl group: ring strain predisposes to rearrangement/cleavage under activating conditions.

Because of sensitivity, any synthetic manipulation should be performed at controlled temperature, minimized basicity, and with rapid workups to capture intermediates. Analytical monitoring (LC–MS, HPLC–UV) is essential.

Target Specificity

Not applicable. This product is a small-molecule natural product standard, not an antibody, probe, or targeted biological reagent. No antigen/epitope or species reactivity applies.