Chlorogenin , CAS No.562-34-5

CAS: 562-34-5 Cat. No.: C1002980 Fórmula: C₂₇H₄₄O₄ Peso molecular: 432.600

Storage

Room temperature

Specifications

Condiciones de almacenamiento de almacenamiento

Room temperature

Nombres e identificadores

• Sonrisas canónicas: C[C@@H]1CC[C@@]2([C@H]([C@H]3[C@@H](O2)C[C@@H]4[C@@]3(CC[C@H]5[C@H]4C[C@@H]([C@@H]6[C@@]5(CC[C@@H](C6)O)C)O)C)C)OC1
• IUPAC Name: (1R,2S,4S,5'R,6R,7S,8R,9S,12S,13R,16S,18S,19S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-16,19-diol
• InChIKey: PZNPHSFXILSZTM-JUGSJECZSA-N
• INCHI: 1S/C27H44O4/c1-15-5-10-27(30-14-15)16(2)24-23(31-27)13-20-18-12-22(29)21-11-17(28)6-8-25(21,3)19(18)7-9-26(20,24)4/h15-24,28-29H,5-14H2,1-4H3/t15-,16+,17+,18-,19+,20+,21-,22+,23+,24+,25-,26+,27-/m1/s1
• Peso molecular: 432.600

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Clase Prenol lipids
      • Subclass Triterpenoids

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Clase: Prenol lipids
• Subclass: Triterpenoids
• Intermediate Tree Nodes: Not available
• Direct Parent: Triterpenoids
• Alternative Parents: Spirostanes and derivatives 6-hydroxysteroids 3-beta-hydroxysteroids Ketals Oxanes Tetrahydrofurans Secondary alcohols Cyclic alcohols and derivatives Oxacyclic compounds Hydrocarbon derivatives
• Molecular Framework: Aliphatic heteropolycyclic compounds
• Substituents: Triterpenoid - Spirostane skeleton - 3-hydroxysteroid - 6-hydroxysteroid - Hydroxysteroid - 3-beta-hydroxysteroid - Steroid - Ketal - Oxane - Tetrahydrofuran - Cyclic alcohol - Secondary alcohol - Acetal - Organoheterocyclic compound - Oxacycle - Organic oxygen compound - Organooxygen compound - Alcohol - Hydrocarbon derivative - Aliphatic heteropolycyclic compound
• Descripción: This compound belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.
• 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

Propiedades químicas y físicas

• Peso molecular: 432.600 g/mol
• XLogP3: 5.100
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 432.324 Da
• Monoisotopic Mass: 432.324 Da
• Topological Polar Surface Area: 58.900 Ų
• Heavy Atom Count: 31
• Formal Charge: 0
• Complexity: 726.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 13
• 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 bioassay or immunoassay protocols are provided for this item. For analytical use, typical starting points include:

• HPLC (RP): C18, 30–60% MeOH or ACN in water over 15–30 min; flow 0.5–1.0 mL/min; detect by ELSD/CAD or UV at 200–210 nm.
• NMR: 10–20 mg/mL in CDCl3, CD3OD, or DMSO-d6; reference to residual solvent peaks; acquire NOESY/ROESY for stereochemical assignments.
• TLC: Silica gel; hexanes/EtOAc 3:1 to 1:1; visualize with anisaldehyde or vanillin stain, heat to develop color.

These are general literature-style procedures to aid method development and are not validated specifications for this product.

Biological Roles

• General context (literature): Chlorogenin is classified as a plant-derived steroidal sapogenin (spirostane-type) that occurs as the aglycone component of certain saponins. In planta, sapogenins and their glycosides are implicated in defense mechanisms against herbivores and pathogens owing to their surfactant-like membrane-disrupting properties at sufficient concentrations.

• Biochemical behavior:

  • Amphiphile features: A rigid hydrophobic steroid core combined with polar hydroxyl groups confers surface activity when glycosylated (saponins), influencing membrane permeability and protein-lipid interactions in model systems.
  • Metabolic origins: Biosynthesized from the isoprenoid/mevalonate pathway, advancing through cycloartenol/lanosterol-like intermediates to spirostane frameworks via plant-specific oxidations and spiroketalization steps (literature/general for sapogenins).

• Research relevance:

  • Tool compound for studying membrane disruption, cholesterol interactions, and micelle/vesicle formation when converted to saponins.
  • Reference standard for phytochemical fingerprinting and quality control of botanical extracts containing related saponins.

Note: This information is provided for biochemical context only. No medical or clinical claims are made. All uses are for research and laboratory purposes.

Buffer Applications

This compound is a hydrophobic small molecule and is not used to prepare biological buffers. For assay work, dissolve in an appropriate organic cosolvent (e.g., DMSO) and then dilute into the desired buffer, ensuring the final organic content prevents precipitation while remaining compatible with the biological system.

Green Alternatives

While Chlorogenin itself is a target molecule rather than a process solvent, greener choices can be made in its handling, purification, and derivatization.

• Greener processing options (general):

  • Extraction/purification: Prefer bio-based or low-toxicity solvents (ethanol, ethyl acetate) over chlorinated solvents where feasible. Supercritical CO2 with ethanol modifiers can be effective for sapogenins.
  • Glycosylation solvents: Replace dichloromethane with toluene, 2-methyltetrahydrofuran (2-MeTHF), or CPME when compatible with the promoter system; use green activators when possible.
  • Workup: Minimize silicone oil baths; use metal-block heaters. Recycle solvents through in-house distillation.

• Comparative considerations (illustrative):

  • DCM vs EtOAc/2-MeTHF: EtOAc/2-MeTHF reduce chlorinated waste and have better environmental profiles; however, glycosylation rates/solubility may be lower—optimize temperature and concentration.
  • Hexanes vs cyclopentyl methyl ether (CPME): CPME offers broader polarity range and lower peroxide formation tendency than ethers like THF; still manage peroxides per SOP.

• Analytical greener choices:

  • Use ACN-sparing or MeOH-based gradients for HPLC; consider water-rich gradients with ELSD/CAD to reduce organic solvent consumption.

Trade-offs must be validated experimentally to maintain yield, selectivity, and product quality.

Pharmaceutical Uses

• Scope: Chlorogenin is not an excipient or approved drug substance as presented here. It is offered strictly for research use.

• Typical roles in pharmaceutical R&D (general):

  • Reference standard for analytical development and impurity profiling in botanical or natural-product–derived materials rich in steroidal saponins/sapogenins.
  • Semisynthetic starting material for generating analog libraries of sapogenins/saponins to probe developability-relevant properties (solubility, permeability, stability) in discovery research.
  • System suitability and retention marker for chromatographic methods evaluating related steroidal frameworks.

• Regulatory note: No pharmacopeial monograph is cited for this specific item. Any use in regulated settings requires independent qualification, method validation, and specification setting by the user.

No therapeutic or clinical claims are made. For research and laboratory use only.

Physical Properties

• Item-specific (Product Data):

  • Appearance: 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 expectations for steroidal sapogenins (for planning only; verify experimentally):

  • Physical state: Typically a white to off-white crystalline solid (literature, class-based observation for sapogenins).
  • Melting point: Often in the 200–260 °C range depending on hydration/polymorph and exact hydroxylation pattern (literature, class-based; not a specification).
  • Solubility profile: Poorly soluble in water; soluble in polar organic solvents such as methanol, ethanol, acetone, chloroform, ethyl acetate; very soluble in DMSO and DMF (literature/general).
  • Partitioning: Strongly lipophilic due to steroid core; logP expected to be high relative to small polar molecules (literature/general trend for sapogenins).
  • UV characteristics: Typically weak UV absorption above 210–220 nm absent conjugation; quantification often by derivatization or ELSD/CAD in chromatography (literature/general).

• Refractive index, density, pKa, BP: Not specified for this item; refer to CoA/Spec Sheet.

Note: Use literature values only as rough guidance. For method validation and release testing, rely on an item-specific CoA/Spec Sheet and your internal method qualification.

Quality and Grades

• Item-specific (Product Data):

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

• Interpreting grade and purity for steroidal reference materials (general guidance):

  • Reference/analytical grade materials typically emphasize high assay (e.g., ≥95–98% by HPLC or qNMR), well-defined water content, and low levels of structurally related sapogenins.
  • Where relevant, impurity profiling may include epimers (e.g., 25R/25S), dehydration products, or partial oxidation byproducts.
  • If supplied as a hydrate/solvate, documentation should indicate stoichiometry to enable accurate mass correction.

• Stabilizers and form: Sapogenins generally do not require stabilizers; they are typically offered as neat crystalline solids. If any anti-caking agents or form (amorphous vs crystalline) are used, these would be disclosed on the CoA/Spec Sheet.

• Recommended quality checks on receipt (best practices):

  • Verify identity by 1H/13C NMR (characteristic steroid signals, spiroketal carbons), HRMS, and melting range.
  • Assess purity by HPLC with ELSD/CAD or UV at low wavelength; optionally confirm by GC-MS after derivatization (silylation) if appropriate.

Refer to the item’s CoA/Spec Sheet for definitive assay, impurity limits, and test methods.

Reaction and Applications

Chlorogenin, as a spirostane-type sapogenin, is a versatile scaffold for semisynthetic modification and as an aglycone for saponin synthesis.

• Typical transformations (general/literature):

  • O-Glycosylation at the 3β-hydroxyl to access natural or designed saponins via trichloroacetimidate or thioglycoside donors (e.g., Schmidt, Helferich, or Koenigs–Knorr strategies).
  • Selective acylation/carbamate formation of secondary alcohols for prodrug-like derivatives or to modulate lipophilicity.
  • Oxidation of secondary alcohols to ketones (e.g., Dess–Martin, PCC) enabling subsequent stereoselective reductions or olefination.
  • Spiroketal manipulation: acid-catalyzed equilibration to adjust spiroacetal configuration; protective group strategies to steer glycosylation.
  • Late-stage diversification via Mitsunobu inversion (careful with sensitive spiroketal) for access to epimeric series.

• Uses in research workflows:

  • Reference standard for phytochemical profiling and authentication of saponin-containing botanicals (HPLC-ELSD/CAD).
  • Building block for SAR studies of sapogenin/saponin biointerfaces (membrane interactions, surfactant properties) in biochemical research.
  • Material for derivatization to generate analytical markers and impurities for method development.

• Practical tips:

  • Dry glassware/solvents for glycosylations; exclude moisture rigorously.
  • Protect non-participating hydroxyls to improve glycosylation selectivity/yield.
  • Monitor reactions by TLC with anisaldehyde or vanillin stains—sapogenins visualize strongly after heating.

All applications are for research and laboratory use only.

Reaction Conditions

The following are literature/general conditions commonly used with spirostane sapogenins and should be optimized for Chlorogenin in your lab. They are guidance only, not item specifications.

• O-Glycosylation at 3β-OH:

  • Donors: peracetylated trichloroacetimidates or thioglycosides of glucose/galactose/rhamnose.
  • Promoters: TMSOTf (−40 to 0 °C), BF3·Et2O (0 to 25 °C), NIS/TfOH (for thioglycosides).
  • Solvents: DCM, toluene, or 2-MeTHF; ensure anhydrous conditions and 3–5 Å molecular sieves.
  • Typical times: 0.5–16 h depending on donor reactivity and temperature.

• Acylation/carbamylation of secondary OH:

  • Reagents: Ac2O or acyl chlorides with DMAP/Et3N in DCM or pyridine; carbamates via CDI or chloroformates.
  • Temperature: 0–25 °C; monitor by TLC (anisaldehyde stain).

• Oxidation of secondary alcohols:

  • Dess–Martin periodinane (DMP) in DCM or acetonitrile, 0–25 °C; or PCC on silica.
  • Followed by NaBH4/L-Selectride reductions for stereocontrol as needed.

• Spiroketal manipulation:

  • Mild acid catalysis (e.g., PPTS in toluene/MeOH) to equilibrate spiro-centers; quench promptly to avoid degradation.

• Purification and analysis:

  • Normal-phase silica with EtOAc/hexanes ± 1–5% MeOH or IPA; reversed-phase C18 with water/MeOH or water/ACN.
  • Detection: ELSD/CAD, low-λ UV (200–210 nm), or derivatization for UV.

Yields are substrate- and condition-dependent; perform small-scale screens to establish selectivity and conversion.

Safety and Handling

• Item-specific hazard information:

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

• General laboratory precautions for steroidal sapogenins (informational, not a substitute for SDS):

  • Avoid inhalation of dust and contact with skin/eyes. Use appropriate PPE: lab coat, safety glasses, and chemically resistant gloves (e.g., nitrile).
  • Handle powders in a fume hood or ventilated enclosure to minimize dust exposure.
  • First aid (general): If inhaled, move to fresh air; if on skin, wash with soap/water; if in eyes, rinse cautiously with water for several minutes; if ingested, rinse mouth and seek medical attention. Always follow your institution’s protocols.

• Incompatibilities and reactivity (general):

  • Stable organic solid; avoid strong oxidizers and strong acids/bases that can hydrolyze the spiroacetal or deprotect sensitive hydroxyls.
  • Thermal decomposition may generate irritant fumes. Avoid prolonged heating above melting/decomposition.

• Environmental considerations (general):

  • Prevent release to the environment. Collect organic waste/solutions in halogen-free organic waste streams per facility guidelines.

Always consult the item-specific Safety Data Sheet (SDS) for authoritative hazard, exposure control, and disposal information.

Solvent Selection

Chlorogenin is a lipophilic, polyhydroxylated steroidal sapogenin. It is not used as a reaction solvent; solvent choice here pertains to dissolution, purification, and analysis.

• Solubility/miscibility (literature/general):

  • High solubility: DMSO, DMF.
  • Good solubility: methanol, ethanol, isopropanol, acetone, acetonitrile, ethyl acetate, chloroform, dichloromethane.
  • Low solubility: water and aqueous buffers at neutral pH.

• Practical selection by task:

  • Stock solutions for bioassays/analytical: prepare in DMSO (10–50 mg/mL), then dilute into assay buffer with final DMSO ≤1–2% v/v to avoid precipitation.
  • Chromatography: normal-phase (hexanes/EtOAc with small % IPA/MeOH) or reversed-phase (water/ACN or water/MeOH; add 0.1% formic acid to improve peak shape if needed). ELSD/CAD detection recommended.
  • Crystallization: often from ethanol, methanol, or acetone/hexanes mixtures.

• Comparison with alternatives (general):

  • Versus less polar steroids (e.g., diosgenin), chlorogenin-like sapogenins may prefer slightly more polar eluents due to additional hydroxylation.
  • For NMR, CDCl3 is suitable; if solubility is limited, use CD3OD or DMSO-d6.

Always confirm solubility experimentally for your batch and application.

Storage and Reconstitution

• Item-specific (Product Data):

  • Storage Conditions: Room temperature.
  • Shipped in: Not specified for this item; refer to CoA/Spec Sheet.

• General storage guidance for sapogenin solids:

  • Store in a tightly closed container, protected from light and moisture. A desiccator or dry cabinet is recommended for long-term stability.
  • Avoid prolonged exposure to strong acids/bases that may hydrolyze the spiroacetal or modify hydroxyl groups.

• Reconstitution and stock solutions (general):

  • Prepare concentrated stocks in DMSO (e.g., 10–50 mg/mL) or ethanol (5–25 mg/mL). Filter through a 0.22 µm PTFE syringe filter if particulate is present.
  • For aqueous assays, dilute the organic stock into buffer with vigorous mixing; include a nonionic carrier (e.g., 0.1–0.5% Tween 80) if precipitation occurs and is compatible with your system.
  • For NMR, dissolve in CDCl3; if solubility is insufficient, use CD3OD or DMSO-d6 and warm gently (≤40 °C) to aid dissolution.

• Stability notes (general):

  • Neat solid is typically stable for years at ambient conditions when dry and protected from light. Solutions in DMSO/MeOH are best stored at −20 °C, protected from light, and used within weeks; minimize freeze–thaw by aliquoting.

Always refer to the item’s CoA/Spec Sheet and SDS for definitive storage, handling, and stability information.

Structure and Identity

Chlorogenin is a plant-derived steroidal sapogenin (spirostane-type aglycone) commonly encountered as the non-sugar core of certain saponins.

• Item-specific (Product Data):

  • SKU: C1002980
  • CAS: 562-34-5
  • CID: 12303065
  • InChIKey: 291119 (as provided)
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.

• Structural features (general/literature description):

  • Core: Tetracyclic steroid nucleus (A/B/C/D rings) with a C17 side chain forming a spiroketal (spiro[5.5] or spiro[5.6] acetal) typical of spirostane sapogenins.
  • Functional groups: Multiple hydroxyl groups (commonly including a 3β-OH), a spiroacetal linkage at C-22/C-26, and secondary/tertiary alcohol stereocenters.
  • Stereochemistry: Polyfunctional, polycyclic framework with defined trans-fused ring junctions and multiple chiral centers characteristic of plant sapogenins.

• 2D structure in words (general): Four fused cyclohexane/cyclopentane rings (steroid skeleton) bearing a β-oriented hydroxyl at C-3, with a side chain terminating in a cyclic acetal that is spiro-fused to a tetrahydrofuran/tetrahydropyran-like ring. The hydroxylation pattern and spiroketal define its identity relative to other sapogenins (e.g., diosgenin, tigogenin).

Synthetic Utility

Chlorogenin’s spirostane skeleton and polyol pattern offer multiple orthogonal handles that enable rich chemistry for analogue and saponin synthesis.

• Functional group leverage (general/literature):

  • 3β-OH glycosylation to install mono- or oligosaccharide chains; neighboring group participation and donor choice (e.g., trichloroacetimidates, thioglycosides) control α/β selectivity.
  • Secondary alcohol acylations/carbamates tune polarity and protectability; silyl/benzyl protections facilitate site-selective manipulations.
  • Spiroacetal lability under acid provides access to equilibrating mixtures; kinetic vs thermodynamic control can bias spiro-configurations.
  • Oxidation/reduction sequences at C-12/C-16-type positions afford ketones/alcohols enabling further diversification (e.g., Wittig, Horner–Wadsworth–Emmons at derived carbonyls after side-chain modification).

• Retrosynthetic value:

  • Serves as an advanced intermediate that bypasses de novo steroid synthesis, allowing focus on glyco-diversity or peripheral oxidation patterns.
  • Compatible with late-stage diversification strategies, enabling parallel synthesis of analog sets for SAR.

• Analytical considerations:

  • Chirality/stereochemistry are central; verify configuration by NOESY/ROESY and diagnostic 13C shifts of spirocarbons.
  • Use derivatization (e.g., TMS, MSTFA) to enhance GC-MS volatility where needed.

This utility profile makes chlorogenin-type sapogenins effective platforms for synthetic and analytical method development in natural products chemistry.

Target Specificity

Not applicable. Chlorogenin is a small-molecule sapogenin, not a biological targeting reagent (e.g., antibody, ligand with defined receptor specificity in this product context). If your application involves biochemical interaction studies (e.g., membrane models), refer to Biological Roles for general context.