Cabraleadiol - ≥98% , CAS No.67253-01-4

CAS: 67253-01-4 Cat. No.: C946637 PubChem CID: 21625899

GRADE & PURITY ≥98%

Storage

Room temperature

Specifications

Especificaciones y pureza

≥98%

Condiciones de almacenamiento de almacenamiento

Room temperature

Pureza

≥98%

Nombres e identificadores

• Sonrisas canónicas: CC1(C2CCC3(C(C2(CCC1O)C)CCC4C3(CCC4C5(CCC(O5)C(C)(C)O)C)C)C)C
• IUPAC Name: (3R,5R,8R,9R,10R,13R,14R,17S)-17-[(2S,5S)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
• InChIKey: RQBNSDSKUAGBOI-ZNYSIYOKSA-N
• INCHI: 1S/C30H52O3/c1-25(2)21-12-17-29(7)22(27(21,5)15-13-23(25)31)10-9-19-20(11-16-28(19,29)6)30(8)18-14-24(33-30)26(3,4)32/h19-24,31-32H,9-18H2,1-8H3/t19-,20+,21+,22-,23-,24+,27+,28-,29-,30+/m1/s1
• Isómeros SMILES: C[C@@]12CC[C@@H]([C@H]1CC[C@H]3[C@]2(CC[C@@H]4[C@@]3(CC[C@H](C4(C)C)O)C)C)[C@@]5(CC[C@H](O5)C(C)(C)O)C
• PubChem CID: 21625899

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Clase Prenol lipids
      • Subclass Terpene glycosides
        • Level5 Triterpene glycosides
          • Level6 Triterpene saponins

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Clase: Prenol lipids
• Subclass: Terpene glycosides
• Intermediate Tree Nodes: Triterpene glycosides
• Direct Parent: Triterpene saponins
• Alternative Parents: Triterpenoids 3-alpha-hydroxysteroids 14-alpha-methylsteroids Tetrahydrofurans Tertiary alcohols Secondary alcohols Cyclic alcohols and derivatives Oxacyclic compounds Dialkyl ethers Hydrocarbon derivatives
• Molecular Framework: Aliphatic heteropolycyclic compounds
• Substituents: Triterpene saponin - Triterpenoid - 3-hydroxysteroid - 14-alpha-methylsteroid - Hydroxysteroid - 3-alpha-hydroxysteroid - Steroid - Cyclic alcohol - Tetrahydrofuran - Tertiary alcohol - Secondary alcohol - Dialkyl ether - Ether - Oxacycle - Organoheterocyclic compound - Organic oxygen compound - Alcohol - Organooxygen compound - Hydrocarbon derivative - Aliphatic heteropolycyclic compound
• Descripción: This 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: diol - oxolanes - tetracyclic triterpenoid

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: 460.700 g/mol
• XLogP3: 7.200
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 460.392 Da
• Monoisotopic Mass: 460.392 Da
• Topological Polar Surface Area: 49.700 Ų
• Heavy Atom Count: 33
• Formal Charge: 0
• Complexity: 789.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 10
• 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 biological or analytical application protocols are provided for this item. For general practice:

• Prepare a DMSO stock solution at a concentration suitable for your assay or synthesis, filter through 0.2 µm PTFE, and store in aliquots to minimize freeze–thaw.
• For analytical method development, begin with RP‑HPLC gradients (water/MeCN or water/MeOH with 0.1% formic acid) and monitor using low‑UV or ELSD/CAD. Refer to your lab’s SOPs and the SDS for detailed procedures and safety guidance.

Biological Roles

No item-specific biological data are provided for this catalog entry; use is restricted to research only.

Literature/general context for limonoid/triterpenoid diols:

• Origin: commonly isolated from Meliaceae and related plant families; cabraleadiol is reported as a constituent of certain Cabralea species (literature context), reflecting biosynthetic tailoring of a triterpene backbone.
• Role in plants: triterpenoids often participate in chemical defense and signaling, with structural features (hydroxylation/oxidation patterns) modulating interactions with membranes and enzymes.
• Physicochemical behavior: amphiphilic nature may affect membrane partitioning and aggregation in biological media; solubilization strategy (DMSO stock, cyclodextrin inclusion) strongly influences apparent activity in in vitro assays.
• Assay considerations: adsorption to plastics and serum proteins can reduce free concentration; include controls for nonspecific binding and use equilibrated plates.

Good practice in screening (general):

• Confirm identity and purity of the test article prior to biological evaluation (orthogonal NMR/MS) and track stability in assay media by LC‑MS.
• Avoid exceeding solubility limits; implement serial dilutions from a well-characterized DMSO stock and include vehicle controls.

Note: No claims are made regarding biological efficacy, potency, or therapeutic application of this item.

Buffer Applications

Cabraleadiol is a hydrophobic small-molecule natural product and does not serve as a buffering agent. It has no established role in preparing pH buffer systems. For experimental use, dissolution typically requires an organic co‑solvent (e.g., DMSO) prior to dilution into aqueous buffers for assays.

Green Alternatives

While cabraleadiol itself is a substrate, greener choices apply to its handling, purification, and derivatization.

Greener solvent substitutions (general guidance):

• Replace DCM/CHCl3 in workups with EtOAc or 2‑MeTHF when solubility permits.
• Use MeOH/EtOH or isopropanol in place of acetonitrile where chromatographic resolution allows.
• Consider CPME or 2‑MeTHF for acylation/etherification steps as drop-in replacements for THF/DCM.

Small comparison (general):

• Solvent: DCM | Greener alternative: EtOAc or CPME | Tradeoffs: slightly lower dissolving power for very apolar substrates; higher bp aids recovery but slows evaporation.
• Solvent: THF | Greener alternative: 2‑MeTHF | Tradeoffs: similar polarity; improved stability to peroxide formation; different azeotrope behavior.
• Solvent: Acetonitrile | Greener alternative: EtOH/MeOH or propylene carbonate | Tradeoffs: viscosity and UV transparency differ; method re-optimization may be needed.

Operations:

• Favor catalytic over stoichiometric reagents (e.g., DMAP-catalyzed acylations; TEMPO-mediated oxidations with bleach derivatives in biphasic systems when compatible).
• Minimize halogenated waste; use column chromatography with heptane/EtOAc gradients rather than hexanes/DCM where feasible.
• Apply solvent recycling for MeOH/EtOH/EtOAc in preparative work to reduce E-factor.

Pharmaceutical Uses

Item-specific pharmacopeial status or excipient role: Not specified for this item; refer to CoA/Spec Sheet.

General research/manufacturing context:

• Natural product scaffold in discovery: triterpenoid diols are often included in screening decks for hit identification and chemotype exploration.
• Analytical reference: can serve as a reference material for method development in natural product QC/QA workflows (e.g., plant extract standardization), subject to verification of purity and identity.
• Formulation studies (preclinical research only): solubilization in DMSO/PEG400 or lipid-based vehicles may be explored to study physicochemical behavior; no clinical or therapeutic claims are made.

Regulatory note:

• This product is for research use only and is not formulated or certified for human or veterinary administration.
• Any use in regulated environments should be supported by lot-specific documentation (CoA, spectral data), method validation, and appropriate stability data.

Physical Properties

Item-specific specifications (this catalog entry):

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
• Melting point (MP): Not specified for this item; refer to CoA/Spec Sheet.
• Boiling point (BP): Not applicable; compound expected to decompose before boiling under ambient pressure (literature/general for triterpenoids).
• Density: Not specified for this item; refer to CoA/Spec Sheet.
• Refractive index/UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.
• Solubility in water: Typically very low for triterpenoid diols (literature/general). Item-specific solubility not specified.

Literature/general physicochemical expectations for triterpenoid diols:

• State: crystalline solid or amorphous solid depending on polymorph and hydration.
• Solubility: soluble in polar aprotic and protic organic solvents (DMSO, DMF, MeOH, EtOH, acetone, ethyl acetate) to varying extents; enhanced by gentle warming or co-solvents.
• LogP: generally high (hydrophobic core), often >3 for related scaffolds.
• Stability: stable at room temperature in dry conditions; sensitive to strong acids/bases that can cause dehydration, rearrangement, or acyl migration.

Analytical characterization tips (general):

• NMR (CDCl3, CD3OD, DMSO‑d6) commonly used; signal dispersion benefits from higher field strengths.
• HRMS ESI/APCI often yields [M+Na]+ or [M+H]+.
• IR shows broad O–H stretch (3,200–3,500 cm−1) and strong C–O stretches (1,000–1,150 cm−1).

Quality and Grades

Item-specific quality information:

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

Guidance on quality assessment for this scaffold (general):

• Structural integrity: verify by 1H/13C NMR with diagnostic hydroxyl-bearing carbon signals; assess purity by quantitative NMR (qNMR) or HPLC with UV/ELSD as appropriate.
• Chromatographic purity: for screening libraries, ≥95% HPLC purity is commonly targeted; confirm detection wavelength suitability (limonoids often absorb weakly above 210–220 nm).
• Residual solvents: check by GC-HS; botanical isolates can retain EtOAc/MeOH unless carefully dried.
• Water content: assess by Karl Fischer if handling on mg–g scale for moisture‑sensitive derivatizations.
• Metal content: typically low for isolated natural products; ICP-MS only if process demands.

Stabilizers/antioxidants:

• Not specified for this item; refer to CoA/Spec Sheet. In general, no stabilizer is required for neutral diols stored dry and protected from light.

Documentation:

• Lot-specific CoA should list structural confirmation (NMR/MS), purity method and value, and any residual solvent/moisture findings. Request full spectral package for method development or regulatory documentation.

Reaction and Applications

Manufacturer intent: listed in a small-molecule/compound library for research use only. No therapeutic or clinical claims.

Research applications (general for triterpenoid diols like cabraleadiol):

• Reference standard and comparator in natural product chemistry, dereplication, and metabolomics workflows.
• Probe scaffold in phenotypic or target-agnostic screening to explore limonoid chemotypes.
• Semi-synthetic precursor to libraries of esters, carbonates, ethers, and carbamates for SAR studies.

Transformations and derivatizations (general):

• O‑Acylation and O‑carbamoylation: using acid chlorides/anhydrides or CDI/urethanes to tune lipophilicity and stability.
• O‑Alkylation: via Mitsunobu or Williamson ether synthesis (after selective activation/tosylation), enabling attachment of reporter tags or solubilizing groups.
• Oxidation: TEMPO/BAIB or Dess–Martin periodinane to convert secondary alcohol(s) to ketone(s); follow with stereoselective reductions to access epimers.
• Protection strategies: silyl ethers (TBDMS/TBS) or acetonides for site-selective multistep sequences.
• Carbon–carbon modifications: limited on the saturated core, but side-chain manipulations, photoredox HAT functionalizations, or late-stage C–H oxidations may be explored.

Practical tips:

• Many limonoids have closely spaced OH groups; exploit differential acidity/sterics to achieve chemoselectivity (e.g., DMAP-catalyzed acylation at less hindered OH).
• Monitor reactions by TLC with anisaldehyde or vanillin stains; UV absorption can be weak above 220 nm.
• For screening stock preparation, filter 0.2 µm after dissolution in DMSO to remove particulates and ensure reproducibility across assays.

Reaction Conditions

The following are general literature-style conditions for transforming secondary diols in triterpenoid frameworks; optimize for your substrate.

• O‑Acylation: acid chloride (1.1–1.5 eq) or anhydride (1.5–3 eq), base (pyridine, NEt3, or DIPEA), catalytic DMAP (5–10 mol%), solvent DCM or EtOAc, 0 °C to rt, 1–6 h. Monitor for chemoselectivity; sterics often favor the less hindered OH.
• Carbonate formation: CDI (1.2–2 eq) in THF/DMF at rt, then alcohol nucleophile; or triphosgene (phosgene equivalent) under controlled conditions with caution.
• Mitsunobu etherification: ROH (1.5–3 eq), PPh3/DIAD (1.2–1.5 eq each), THF or toluene, 0 °C to rt, 2–12 h; beware elimination or overreactions on hindered centers.
• Oxidation to ketone: Dess–Martin periodinane (1.3 eq) in DCM, 0 °C to rt, 0.5–3 h; or TEMPO/BAIB in MeCN/H2O, rt. Work up with Na2S2O3/NaHCO3 as appropriate.
• Selective reduction: NaBH4 or L‑Selectride in THF/MeOH at −78 to 0 °C for stereocontrol; CBS reduction in toluene/CH2Cl2 with borane for enantiofacial bias on prochiral ketones derived from the diol.
• Protection: TBSCl (1.2–2 eq) + imidazole in DMF at rt to 50 °C; selective installation often achievable due to sterics and hydrogen-bonding patterns.

General tips:

• Use anhydrous conditions and inert atmosphere for moisture‑sensitive steps.
• Test small-scale screens to map regioselectivity across OH sites.
• Characterize intermediates thoroughly (2D NMR) due to potential for acyl migration and rearrangements on polyol frameworks.

Safety and Handling

Authoritative safety information must be taken from the product’s SDS.

Item-specific hazard data:

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

General laboratory safety guidance for neutral polyol natural products:

• PPE: lab coat, safety glasses, and nitrile gloves. Avoid inhalation of dust/particulates and contact with eyes/skin.
• Handling: minimize dust generation; use a fume hood during weighing/dissolution to avoid aerosol formation.
• Storage incompatibilities: separate from strong oxidizers and strong acids/bases that may induce degradation or exothermic reactions.
• Hygroscopicity: many polyols show modest hygroscopic tendencies; keep container tightly closed with desiccant if possible.
• Thermal stability: avoid excessive heat; triterpenoids may char or decompose before melting.

First-aid overview (general, not a substitute for SDS):

• Inhalation: move to fresh air; seek medical advice if symptoms persist.
• Skin/eye contact: rinse with water for at least 15 minutes; remove contaminated clothing; seek medical advice if irritation continues.
• Ingestion: rinse mouth; do not induce vomiting; seek medical attention.

Waste disposal:

• Dispose according to institutional and local regulations for organic laboratory chemicals. Avoid release to the environment; collect solutions/solids in appropriate organic waste streams.

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

Solvent Selection

Cabraleadiol is a hydrophobic polycyclic diol; solvent choice should balance dissolution, stability, and downstream use.

General miscibility/solubility tendencies (literature/general):

• Good: DMSO, DMF, NMP, acetone, ethyl acetate, dichloromethane, chloroform, methanol, ethanol, isopropanol.
• Limited: acetonitrile (case dependent), MTBE, toluene (may require warming or co‑solvent).
• Poor: water and aqueous buffers without co‑solvent or surfactant.

Selection guidance by application:

• Biological screening stocks: prepare in dry DMSO (e.g., 10–50 mM) and dilute into assay buffer with final DMSO ≤0.5–1% v/v to avoid precipitation; include nonionic surfactant if needed.
• Purification: normal-phase or reversed-phase flash/HPLC. RP‑HPLC: water/MeCN or water/MeOH with 0.1% formic acid as modifier; monitor at low UV (200–210 nm) or use ELSD/CAD.
• Derivatization chemistry: choose aprotic polar solvents (DCM, THF, DMF) for acylations/etherifications; add base (pyridine, DIPEA) as appropriate.

Comparative notes:

• DMSO vs DMF: DMSO offers superior solubilization for screening but is harder to remove; DMF is useful in synthesis, miscible with many reagents, and removable under high vacuum.
• MeOH/EtOH: convenient for NMR and recrystallization but can participate in acyl transfer or transesterification under acidic/basic conditions.
• Halogenated solvents (DCM/CHCl3): excellent dissolvers for nonpolar polyols; ensure proper ventilation and waste segregation.

Storage and Reconstitution

Item-specific storage and logistics:

• Storage conditions: Room temperature (per Product Data). Protect from moisture and light; keep container tightly closed.
• Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
• Appearance: Not specified for this item; refer to CoA/Spec Sheet.

Reconstitution and handling (general guidance for triterpenoid diols):

• Stock solutions: dissolve in anhydrous DMSO, DMF, MeOH, or EtOH. For biological assays, DMSO stocks are typical; filter (0.2 µm PTFE) after dissolution.
• Working solutions: dilute DMSO stocks into aqueous buffers immediately before use; maintain final DMSO typically ≤0.5–1% v/v to mitigate precipitation and assay interference.
• Stability: store dry solid at room temperature; for solutions, prefer −20 °C in inert atmosphere (argon) and protect from light. Avoid repeated freeze–thaw by aliquoting.
• Moisture considerations: if hygroscopic behavior is observed, handle quickly on the bench and return to a desiccated cabinet; dry under high vacuum at ambient temperature if necessary prior to sensitive reactions.

Labeling and documentation:

• Record solvent, concentration, preparation date, and lot number on all aliquots. Consult the CoA/SDS for any additional storage or incompatibility notes.

Note: For research use only.

Structure and Identity

Cabraleadiol is a plant-derived small molecule natural product typically classified as a limonoid/triterpenoid-type diol scaffold.

• SKU: C946637; CAS: 67253-01-4; CID: 21625899 (catalog reference)
• Molecular formula (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
• SMILES (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
• InChIKey (item-specific): Not specified for this item; refer to CoA/Spec Sheet.

Structural features (literature/general):

• Polycyclic, highly fused triterpenoid framework consistent with limonoid skeletons.
• Contains at least two alcohol functions (–OH), typically secondary, enabling derivatization (e.g., ester, carbonate, ether formation).
• Multiple stereogenic centers and a rigid, compact 3D conformation; chirality is integral to identity and bioactivity profiling.
• Largely apolar hydrocarbon core with localized polar hydroxyl groups, conferring amphiphilic behavior in organic media and poor aqueous solubility.

2D description in words (literature/general):

• A tetracyclic or pentacyclic carbon framework reminiscent of oxidized triterpenes, bearing hydroxyl substituents on distinct ring junctions or side-chain positions; few to several ring junction stereocenters define a specific stereochemical pattern. Any enone/lactone motifs sometimes observed in limonoids are context-dependent and should be verified on the CoA for this lot.

Identity confirmation best practices:

• Use orthogonal methods: HRMS for exact mass, 1D/2D NMR for ring substitution/stereochemistry, and, when needed, chiroptical methods (CD/ORD) or single-crystal XRD.

Synthetic Utility

Cabraleadiol, as a polycyclic diol, is a versatile starting point for semi-synthesis and late-stage functionalization.

Functional groups and handles (general):

• Two alcohol groups (often secondary) enable formation of esters, ethers, carbonates, and carbamates; selective protection allows stepwise manipulation.
• The rigid, sterically congested core confers diastereoselective outcomes in oxidations/reductions and can template face-selective additions.

Typical transformations (general):

• Site-selective acylation: DMAP-catalyzed acylations to install differentiating protecting groups, steering further chemistry.
• Mitsunobu inversion at a chosen OH to access epimers or install functionalized ethers; monitor for overreaction and elimination.
• Oxidation to ketone(s) (DMP, PCC, TEMPO systems), followed by stereocontrolled reduction (CBS, NaBH(OAc)3) to diversify stereochemistry.
• Carbonate/carbamate linkers: CDI or triphosgene alternatives for pro-moiety synthesis and conjugation to tags/polymers.
• Sulfonate activation (tosyl/mesyl) to enable substitution, ring-closure attempts, or tether installation for macrocyclizations.

Retrosynthetic value:

• Provides a densely functionalized, conformationally restricted scaffold to explore 3D-rich chemical space; advantageous in fragment growth and lead optimization when flatness penalties apply.

Analytical and purification notes:

• Weak chromophores necessitate low-UV detection or ELSD/CAD in HPLC; TLC visualization with anisaldehyde/sulfuric stains is recommended.
• Diastereomeric mixtures may arise; resolve by chiral SFC or RP‑HPLC with shallow gradients.

Target Specificity

This product is a small-molecule natural product and is not an antibody, enzyme, or ligand with defined biomolecular target specificity in this catalog entry. No item-specific target data are provided.