Pseudotaraxasterol , CAS No.464-98-2

CAS: 464-98-2 Cat. No.: P1445962 PubChem CID: 12305110

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

개요

Pseudotaraxasterol shows cytotoxic activity against MOLT-4 cells.

Specifications

보관 조건

Store at -20°C

배송

Ice chest + Ice pads

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이름과 식별자

정식 스마일

CC1C2C3CCC4C5(CCC(C(C5CCC4(C3(CCC2(CC=C1C)C)C)C)(C)C)O)C

IUPAC Name

(3S,4aR,6aR,6aR,6bR,8aS,12S,12aR,14aR,14bR)-4,4,6a,6b,8a,11,12,14b-octamethyl-2,3,4a,5,6,6a,7,8,9,12,12a,13,14,14a-tetradecahydro-1H-picen-3-ol

InChIKey

NGFFRJBGMSPDMS-ZJJHUPNDSA-N

INCHI

1S/C30H50O/c1-19-11-14-27(5)17-18-29(7)21(25(27)20(19)2)9-10-23-28(6)15-13-24(31)26(3,4)22(28)12-16-30(23,29)8/h11,20-25,31H,9-10,12-18H2,1-8H3/t20-,21-,22+,23-,24+,25-,27-,28+,29-,30-/m1/s1

이성체 SMILES

C[C@H]1[C@@H]2[C@H]3CC[C@@H]4[C@]5(CC[C@@H](C([C@@H]5CC[C@]4([C@@]3(CC[C@]2(CC=C1C)C)C)C)(C)C)O)C

대체 CAS

464-98-2

PubChem CID

12305110

Application Protocols

No vendor-validated bioassay protocols are specified for this item.

• General usage examples (informational):
  • HPLC analysis: Prepare a ~1–2 mg/mL stock in acetonitrile or methanol (sonicate/warm gently). Inject onto C18 with high organic (≥90% MeOH/H2O) and ELSD/CAD detection.
  • GC–MS (derivatized): Convert to TMS ether (BSTFA + 1% TMCS, 60–70 °C, 30–60 min), dilute in hexane, and analyze on nonpolar columns.
  • Solubility screening: Create serial dilutions in DMSO or ethanol, then dilute into assay medium while keeping final organic <1–2% v/v, using surfactants if necessary.

Refer to your internal SOPs and the literature for method details; adjust to instrument and matrix.

Biological Roles

Biochemical context (literature, informational):

• Source and occurrence:

  • Pseudotaraxasterol is a plant-derived pentacyclic triterpenol, reported in resins and cuticular waxes of various angiosperms (notably Asteraceae and related taxa). It often co-occurs with taraxasterol/taraxerol.

• Biosynthetic context:

  • Formed via cyclization of squalene epoxide by oxidosqualene cyclases to taraxastane-type skeletons, followed by enzyme-mediated rearrangements and oxidations that define isomeric triterpenol profiles.

• Biological function in plants:

  • Contributes to the hydrophobic barrier properties of cuticles and resins, aiding in water retention and physical/biotic stress resistance. Triterpenols can serve as precursors to more oxidized triterpenoids and saponins that participate in plant–environment interactions.

• Analytical/omics relevance:

  • Used as a chemical marker in chemotaxonomy and metabolomics of plant extracts. Accurate quantification supports studies of triterpenoid pathway regulation and environmental effects on metabolite composition.

Note: All roles described are biochemical/analytical in research organisms. This product is for research use only; no clinical or diagnostic use implied.

Buffer Applications

This compound is a highly hydrophobic triterpenoid and is not used to formulate aqueous buffer systems. It has negligible water solubility and lacks acid/base functionality suitable for buffering.

• Practical note: If incorporation into aqueous assays is required, prepare concentrated stocks in DMSO or ethanol and dilute into aqueous media containing appropriate solubilizers (e.g., nonionic surfactants) while keeping final organic content low to avoid assay interference.

Green Alternatives

While the compound itself is a target analyte/starting material, greener practices relate to extraction, purification, and derivatization workflows.

• Solvent substitutions (literature-informed suggestions):

  • Replace chlorinated solvents (CH2Cl2, CHCl3) with cyclopentyl methyl ether (CPME) or 2-methyltetrahydrofuran (2-MeTHF) for workups/extractions when solubility allows.
  • Use EtOAc/hexane or heptane/IPA gradients in flash chromatography instead of dichloromethane-based systems.
  • For crystallizations, consider greener alcohols (ethanol, isobutanol) or ethyl acetate rather than toluene/benzene.

• Energy/resource efficiency:

  • Employ room-temperature reactions where possible (e.g., silylation often proceeds at ambient temperature). Use microscale reactions for method development to limit solvent consumption.

• Trade-offs:

  • Solubility of highly lipophilic triterpenes may be inferior in some green solvents; modest warming or co-solvent systems (EtOAc with small % IPA) may be necessary.
  • ELSD/CAD detectors allow avoidance of UV-active derivatization, reducing reagent waste.

• Waste minimization:

  • Pool fractions via on-the-fly TLC/CAD to reduce re-chromatography. Recycle non-halogenated solvent mixtures after distillation when appropriate and compliant with facility policies.

Pharmaceutical Uses

No pharmacopeial monograph or excipient role is specified for this item; refer to CoA/Spec Sheet for any regulatory notes.

• Research/manufacturing context (informational):

  • Employed as a reference standard for phytochemical QC of botanically derived raw materials.
  • Investigational use as a scaffold for semi-synthetic derivatization to evaluate physicochemical properties (solubility, permeability) of triterpenoid analogs in pre-formulation research.
  • Can serve as a hydrophobic phase component in model membranes/lipid films for biophysical studies, analogous to other neutral triterpenoids/sterols.

• Important limitations:

  • For research use only. Not intended for human or veterinary therapeutic, diagnostic, or clinical applications.
  • Any application in regulated manufacturing would require independent qualification and specification setting; such status is not provided here.

Physical Properties

• Item-specific properties (from 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.

• Literature/computed properties (informational, not product specifications):

  • Physical state: Typically a white to off-white crystalline solid (literature, triterpenols).
  • Solubility: Practically insoluble in water; soluble in nonpolar/weakly polar organic solvents such as hexane, toluene, chloroform, dichloromethane, ethyl acetate; moderate solubility in hot ethanol or isopropanol; good solubility in DMSO (literature).
  • Polarity/logP: Highly lipophilic; very high partition coefficient (logP often >8 for similar triterpenols; literature).
  • UV/Vis: No strong chromophores; weak UV absorption above ~210–220 nm typical for saturated triterpenes (literature).
  • Melting behavior: Many pentacyclic triterpenols melt in the ~200–250 °C range (literature, compound-dependent). Specific MP for this item is not provided.
  • Density/refractive index/optical rotation: Not specified for this item; refer to CoA/Spec Sheet.

Notes for handling based on properties:

• Low volatility; thermally stable under brief heating but may isomerize/oxidize at elevated temperatures.
• The tertiary alcohol enables derivatization (e.g., esterification, silylation) to improve solubility/volatility for GC analysis.

Quality and Grades

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

• Interpreting typical grades (general guidance):

  • Research grade triterpenoids are commonly specified by HPLC or GC purity (e.g., >95% area). Absence of grade here means you should consult the CoA for exact assay, residual solvents, and identification tests (e.g., 1H/13C NMR, MS).
  • For analytical applications (reference standard), preference is usually for ≥95–98% purity with well-documented chromatographic identity and low isomeric impurities, as structural isomers (taraxasterol/taraxerol) can co-occur in botanicals.

• Stabilizers/additives:

  • No stabilizer is indicated for this item. If required, users sometimes add trace antioxidants (e.g., BHT) for long-term storage of unsaturated triterpenoids; evaluate impact on assays before use.

• What to check on receipt:

  • Verify batch-specific purity, water content, and identity (CoA). Inspect for discoloration (yellowing can indicate oxidation) or clumping due to static/handling.
  • For quantitative work, obtain a chromatographic reference trace (HPLC/GC) and record a fresh NMR where appropriate.

Reaction and Applications

As a pentacyclic triterpenol, pseudotaraxasterol serves both as a natural product standard and as a substrate for semi-synthetic modification.

• Analytical/standard uses:

  • Reference material for profiling of plant triterpenoids by HPLC-UV/ELSD, LC–MS, or GC–MS after derivatization (e.g., TMS ethers). Useful as a system suitability/retention marker in normal-phase separations of resin/triterpene fractions.

• Functional group transformations (literature examples):

  • Alcohol chemistry: Esterification (acyl chlorides/anhydrides), carbonate/urethane formation, Mitsunobu inversion (if secondary/allylic OH contexts are exploited in derivatives), and silylation (TMS/TBDMS) for GC volatility.
  • Oxidations: TEMPO/bleach or Dess–Martin to convert the tertiary alcohol (where applicable) to ketone is often limited; more commonly, allylic/benzylic oxidations (SeO2, Cr(VI)-free methods) at activated positions of the skeleton.
  • Olefin manipulation: Epoxidation (mCPBA), hydroboration–oxidation, or selective hydrogenation of endocyclic double bonds to probe structure–activity or generate saturated analogs.
  • Glycosylation: Conversion to saponin-like structures via installation of glycosides at the hydroxyl (Koenigs–Knorr/modern donors) to modulate solubility.

• Purification/characterization tips:

  • Due to weak UV chromophores, use ELSD/CAD for HPLC detection; GC–MS of TMS derivatives offers diagnostic fragmentation for isomer differentiation.
  • 1D/2D NMR (especially HMBC/NOESY) is often required to distinguish pseudotaraxasterol from taraxasterol/taraxerol isomers.

• Practical considerations:

  • Reactions benefit from rigorously anhydrous conditions and inert atmosphere. Control temperature to prevent skeletal rearrangements.

Reaction Conditions

General conditions drawn from literature for pentacyclic triterpenols (informational; optimize per substrate):

• Protection/derivatization:

  • Silylation (TMSCl or TBDMSCl): Imidazole or pyridine, CH2Cl2 or DMF, 0–25 °C, 0.5–2 h. Workup with aqueous NH4Cl; monitor by TLC/GC.
  • Acylation (Ac2O or acyl chlorides): Pyridine or DMAP catalysis in CH2Cl2/Et3N, 0–25 °C, 1–4 h.

• Olefin functionalization:

  • Epoxidation: mCPBA (1.1–1.5 eq) in CH2Cl2, 0 °C to rt, 1–3 h; buffer with NaHCO3 to minimize rearrangements. Typical isolated yields 60–85% depending on site selectivity (literature).
  • Hydroboration–oxidation: 9-BBN or BH3·THF, 0 °C to rt, followed by H2O2/NaOH; protic workups can induce rearrangements—quench carefully. Yields vary widely (40–80%).
  • Hydrogenation: Pd/C (5–10%), EtOH/EtOAc, 1–5 bar H2, rt–40 °C, 2–12 h; monitor to avoid over-reduction.

• Glycosylation at OH:

  • Trichloroacetimidate donors with TMSOTf (0.05–0.2 eq) in CH2Cl2 or toluene, −20 to 0 °C, 1–6 h; protect other nucleophiles if present. Typical yields 50–75% (literature).

• Oxidation strategies:

  • Allylic oxidation: SeO2 or catalytic methods (e.g., Mn-catalyzed) in refluxing dioxane/toluene; caution: skeletal rearrangements possible. Yields 30–70%.

Notes:

• Employ inert atmosphere, anhydrous solvents, and low light when relevant. Confirm product identity by comprehensive NMR due to isomerization risk.
• The above are general literature guidelines and not specifications for this item.

Safety and Handling

• GHS/SDS information (item-specific):

  • 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 safety guidance (informational):

  • Likely low acute toxicity based on class; treat as a combustible organic solid. Avoid generating dust/aerosols.
  • PPE: Lab coat, safety glasses, and suitable chemical-resistant gloves (e.g., nitrile). Use in a fume hood when weighing/dissolving.
  • Incompatibilities: Strong oxidizers (risk of exothermic reaction/oxidation). Prolonged exposure to air/light may promote slow oxidation of the allylic/tertiary alcohol site.
  • First aid (general): If inhaled—move to fresh air; if on skin—wash with soap/water; if in eyes—rinse cautiously with water; if ingested—rinse mouth and seek advice. Always follow institutional protocols.
  • Fire safety: Use CO2, dry chemical, or foam. Product may form irritating fumes when burned.

• Best practices:

  • Handle under inert atmosphere (nitrogen/argon) for long manipulations to minimize oxidation.
  • Keep containers tightly closed; minimize repeated warming/cooling cycles.
  • Defer to the product SDS for authoritative hazard, exposure limits, and disposal guidance.

Solvent Selection

Pseudotaraxasterol is highly hydrophobic; solvent choice focuses on nonpolar to moderately polar organic media.

• Solubility/miscibility profile (literature, general):

  • Good: Hexane, heptane, toluene, xylene, chloroform, dichloromethane, ethyl acetate, THF.
  • Moderate (often requires warming/sonication): Ethanol, isopropanol, acetone, acetonitrile.
  • Poor/immiscible: Water and aqueous buffers.
  • Stock solutions for bioassays are commonly prepared in DMSO or ethanol, then diluted into media containing surfactants or carrier proteins (as allowed by the assay design).

• Practical guidance:

  • For chromatography: Normal-phase (hexane/EtOAc) works well; add small percentages of isopropanol for sharper bands if needed. Reverse-phase (MeOH/H2O or ACN/H2O) requires high organic content; consider pre-dissolving in MeOH or ACN.
  • For derivatization/GC: Use anhydrous solvents (e.g., pyridine, dichloromethane) with silylating agents; ensure complete dissolution before reaction.

• Comparison with related matrices:

  • Versus sterols (cholesterol): Similar nonpolarity; however, triterpenols can be less soluble in short-chain alcohols; aromatic chlorinated solvents often enhance solubility.

• Handling tips:

  • Mild warming (30–50 °C) and ultrasonication aid dissolution. Avoid prolonged heating that could induce isomerization or oxidation.

Storage and Reconstitution

• Item-specific storage/shipping (from Product Data):

  • Storage Conditions: Store at −20 °C.
  • Shipped In: Ice chest + Ice pads.

• General handling guidance:

  • Protect from light and air to limit oxidation/isomerization. Store in amber, tightly sealed vials; consider inert gas backfill for long-term storage.
  • Allow container to equilibrate to room temperature before opening to minimize moisture condensation.

• Reconstitution (informational):

  • Prepare concentrated stocks (e.g., 10–50 mg/mL) in DMSO, ethanol, or chloroform, depending on application. Sonication and mild warming (≤40–50 °C) can aid dissolution.
  • For aqueous work, dilute organic stocks into buffered media with surfactants or carriers; verify that the final organic solvent content is compatible with your system.

• Stability considerations:

  • Avoid repeated freeze–thaw cycles; aliquot stocks upon first reconstitution. Monitor for discoloration or precipitation over time.
  • Shelf-life and exact stability are not specified for this item; refer to CoA/Spec Sheet and perform periodic QC (e.g., HPLC) for critical applications.

• Disposal: Dispose of organic solutions and residues according to institutional and local regulations for nonhalogenated/halogenated organic waste as appropriate.

Research Use Note: For research use only.

Structure and Identity

Brief overview: Pseudotaraxasterol is a pentacyclic triterpenoid alcohol (triterpenol), an isomer of taraxasterol, commonly occurring in plant resins and cuticular waxes.

• Item-specific identifiers (from Product Data):

  • SKU: P1445962
  • Product Name: Pseudotaraxasterol
  • CAS: 464-98-2
  • InChIKey: 237748 (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/typical identity (informational):

  • Chemical class: Pentacyclic triterpenol (taraxastane-type skeleton)
  • Core features: Five fused alicyclic rings (steroid-like framework) with multiple quaternary centers; one tertiary alcohol; one or more endocyclic double bonds depending on isomerization pattern.
  • Stereochemistry: Multiple defined stereocenters typical of triterpenes; pseudotaraxasterol differs from taraxasterol by double-bond placement/stereochemical configuration in the E-ring region (literature).

• 2D structural description (general):

  • A compact, highly substituted polycyclic hydrocarbon framework (C30 backbone) bearing a single hydroxyl group on a bridgehead/tertiary carbon; several angular methyl groups decorate the rings, conferring high hydrophobicity.

Synthetic Utility

Pseudotaraxasterol offers a dense, stereochemically rich scaffold for synthesis.

• Functional group handles:

  • Tertiary alcohol: amenable to esterification, carbonate formation, silylation; less reactive toward simple oxidation to carbonyls but can undergo dehydration or rearrangement under acidic conditions.
  • Endocyclic C=C bond(s): subject to epoxidation, hydroboration–oxidation, ozonolysis (with care to avoid over-fragmentation), and catalytic hydrogenation.

• Retrosynthetic value:

  • Provides access to a family of taraxastane-derived ketones, epoxides, and glycosides. Strategic protection of the alcohol allows selective modification of olefins and vice versa.

• Named/typical transformations (literature):

  • Epoxidation with mCPBA followed by ring opening to introduce vicinal diols or rearranged motifs.
  • Radical bromination (NBS/AIBN) at activated positions followed by substitution/elimination to diversify.
  • Formation of TMS/TBDMS ethers to enable GC–MS analysis and volatility for micro-scale manipulations.
  • Koenigs–Knorr or trichloroacetimidate glycosylations at the OH to generate saponin-like conjugates, enhancing aqueous compatibility.

• Analytical support:

  • NMR (1H, 13C, DEPT, HSQC, HMBC) is critical for confirming site-selective modifications; HRMS verifies molecular changes given minimal UV signatures.

Target Specificity

Not applicable. This product is a small-molecule triterpenoid, not a biological targeting reagent (e.g., antibody, peptide ligand). No antigen/epitope or species reactivity applies.