This compound belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.
External Descriptors
Not available
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.
Certificats (CoA, COO, BSE/TSE et tableau d'analyse)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Propriétés chimiques et physiques
Poids moléculaire
442.700 g/mol
XLogP3
7.500
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
0
Exact Mass
442.381 Da
Monoisotopic Mass
442.381 Da
Topological Polar Surface Area
40.500 Ų
Heavy Atom Count
32
Formal Charge
0
Complexity
795.000
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
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Application Protocols
No assay-specific protocols are provided for this item. As general guidance for handling hydrophobic small molecules in research settings:
Stock preparation: Weigh accurately, then dissolve in dry DMSO or CH2Cl2/EtOH mixture to prepare a concentrated stock (e.g., 10–50 mM). Sonication and mild warming can assist dissolution.
Working solutions: For HPLC, dissolve in MeOH/CH3CN with a small amount of DCM or IPA if needed. For GC–MS, convert to TMS ethers (BSTFA + 1% TMCS, 60–70 °C, 30–60 min) to improve volatility (general practice).
Bioassay addition: Add from DMSO stock to aqueous media with vigorous mixing; maintain final DMSO ≤1–2% v/v unless your system tolerates higher. Consider cyclodextrin carriers for enhanced apparent solubility.
Storage of solutions: See Storage & Reconstitution; minimize freeze–thaw of DMSO stocks by aliquoting.
For any validated, application-specific parameters (e.g., LC–MS transition lists, derivatization times), refer to your internal SOPs or method development notes; none are provided with this listing.
Biological Roles
No biological data are provided for this specific catalog item. The following describes general, literature-reported roles for serratene-type triterpenoids in nature (not product-specific, not medical claims):
Occurrence: Serratene triterpenoids are reported from various plants (including certain conifers and ferns) and occasionally from lichens. They are constituents of epicuticular waxes and resins (literature, general).
Putative functions in source organisms: Contribute to cuticular barrier properties, reducing transpiration and offering defense against herbivores or pathogens via physical and chemical means.
Biophysical behavior: Due to their rigid, polycyclic skeletons and high hydrophobicity, these molecules can intercalate into lipid phases, modulating membrane order and surface hydrophobicity (biophysical literature, general).
Chemotaxonomy: Profiles of serratene-type triterpenoids may aid in species differentiation and ecological studies; authentic standards support targeted and untargeted metabolomics.
Analytical implications: Their low UV chromophore density requires ELSD/CAD or MS detection in HPLC; GC–MS analysis typically involves silyl derivatization to achieve volatility and symmetrical peaks.
Important: Any discussion of biological effects in cells or organisms must be generated from primary literature for the exact isomer and context. This catalog item is provided strictly for research use; no clinical or diagnostic use is implied.
Buffer Applications
Serratenediol is a highly hydrophobic triterpenoid diol and is not used as a buffering agent. It lacks acid–base pairs in the physiological pH range suitable for buffer capacity.
Practical notes:
For experiments requiring this compound in aqueous buffers, prepare concentrated stocks in DMSO or ethanol and add to the buffer with vigorous mixing. Maintain final co-solvent content at levels compatible with the biological or analytical system (commonly ≤1–2% v/v).
Use cyclodextrins, lipid carriers, or surfactants (e.g., Tween 80 at low percentages) if higher apparent aqueous solubility is required, and validate that carriers do not interfere with readouts.
If your workflow truly needs pH control, select an appropriate buffer system (e.g., phosphate, HEPES) independent of this analyte.
Green Alternatives
Greener handling of hydrophobic triterpenoids focuses on solvent substitution and efficient workups.
Comparison (general guidance):
Conventional vs. greener choices:
Chlorinated solvents (CH2Cl2, CHCl3) → consider 2-MeTHF, CPME, ethyl acetate, or toluene when compatible with solubility and reactivity.
Pyridine for acylations → consider Et3N/DMAP in EtOAc or 2-MeTHF, or ionic liquids for catalytic media (literature, general).
Multiple silica columns → favor crystallization or trituration when possible; apply flash gradients with greener eluents (heptane/EtOAc).
Trade-offs:
2-MeTHF and CPME offer higher hydrophobic solubilization and water immiscibility, easing workups; however, they can retain peroxides—validate inhibitor levels and apply peroxide testing in long-term storage (general caution).
EtOAc is biodegradable and widely available but may provide lower solubility for bulky diols; modest warming and concentration cycling can help.
Supercritical CO2 (with EtOH modifier) can extract/clean triterpenoids at scale, reducing solvent residues, but requires specialized equipment.
Workflow tips:
Design reactions for high atom economy (e.g., catalytic acylations) and minimize protecting group steps.
Use microscale scouting to identify the least hazardous solvent that still achieves target solubility and rate.
Implement recycling of nonpolar eluents where facility infrastructure permits.
Pharmaceutical Uses
No pharmacopeial status or excipient role is specified for this item. This product is supplied strictly for research use only.
Context (general, non-clinical):
Reference standard: Natural-product diols like serratenediol can serve as standards for identity testing, impurity profiling, or stability-indicating methods in botanical or fermentation-derived materials.
Formulation research: In pre-formulation or delivery science, highly lipophilic diols may be used as model hydrophobes to study solubilization in lipid-based systems (self-emulsifying formulations, micelles, cyclodextrin inclusion). These are research activities, not therapeutic claims.
Solid-state studies: The polycyclic, rigid structure makes triterpenoids useful surrogates for exploring crystallinity–solubility relationships and the impact of amorphization or co-amorphous strategies.
Important: Do not infer any therapeutic use, safety, or efficacy from the presence of this research chemical in a lab catalog. For regulated development, consult primary data and compendial requirements, and obtain GMP-grade materials when appropriate.
Physical Properties
Item-specific numerical specifications are not provided in the Product Data. The following are general expectations for serratene-type triterpenoid diols from the literature and practitioner experience; do not treat these as specifications.
Appearance: Not specified for this item; refer to CoA/Spec Sheet. (Triterpenoid diols are often white to off-white crystalline solids or amorphous powders.)
Melting behavior (literature, general): Many pentacyclic triterpenoid diols exhibit melting in the approximate 180–260 °C range, with possible softening/sintering and partial decomposition depending on substitution and purity.
Boiling point: Not typically distilled; such high-MW triterpenoids decompose before boiling at atmospheric pressure (literature, general). If purification is needed, rely on recrystallization or chromatography.
Density/refractive index: Not applicable/rarely reported for solids of this class. Not specified for this item; refer to CoA/Spec Sheet.
Solubility (literature, general):
Water: Practically insoluble.
Organic: Soluble in chlorinated solvents (e.g., CH2Cl2, CHCl3), moderately to well soluble in EtOAc and THF, and typically soluble in DMSO; limited solubility in MeOH/EtOH unless heated or with co-solvent.
pKa/logP: Alcohol pKa high (non-ionizing under neutral conditions); very high hydrophobicity (triterpenoids often exhibit logP >> 5; literature, general trend).
Always confirm critical handling parameters (solubility, melting behavior) empirically with a small test portion under your specific conditions.
Quality and Grades
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Context and guidance for this compound class:
For natural-product standards like triterpenoid diols, purity assessment typically relies on a combination of HPLC/UPLC chromatographic purity, 1H/13C NMR, HRMS, and, where relevant, optical rotation and melting range. If your application is quantitative (e.g., analytical standard), verify both purity and identity by orthogonal methods.
Chromatography-grade materials: When intended for LC assay calibration, low UV baseline drift and absence of late-eluting nonpolar impurities are important; request chromatograms if not provided in the CoA.
Residual solvents and water: Not specified for this item. For moisture-sensitive derivatizations (e.g., silylations), consider gentle drying in vacuo at ambient to 40 °C prior to use.
Stereochemical integrity: Pentacyclic triterpenes can exhibit multiple stereocenters; ensure the specific isomer and configuration match your method validation or reference spectra.
Stabilizers/Additives: Not specified for this item; this class ordinarily does not require stabilizers. If present, they will be listed on the CoA.
Recommendation: Align the item’s certificate data with your intended use (synthetic precursor vs. analytical reference). For regulated workflows, retain batch-specific CoA and spectral data in your documentation.
Reaction and Applications
Without item-specific application notes, the following summarizes common laboratory uses for serratene-type triterpenoid diols.
Analytical reference: Used as a reference standard in natural products research, phytochemical profiling, and dereplication workflows. Calibration in LC–MS or GC–MS typically involves prior derivatization (e.g., trimethylsilyl ethers) to enhance volatility and peak shape (literature, general).
Derivatization chemistry:
Esterification (e.g., acetates, benzoates) to probe steric/electronic effects or for protecting groups in multistep sequences.
Silylation (TMS, TBDMS) to improve GC amenability and to modulate polarity during chromatographic separations.
Oxidations (e.g., Dess–Martin, TEMPO) to aldehydes/ketones at benzylic/tertiary positions where accessible, followed by further elaboration.
Semisynthesis: Triterpenoid diols serve as chiral, densely functionalized platforms for preparing libraries of analogs (e.g., carbamates, carbonates, cyclic acetals) for structure–property investigations (solubility, membrane interaction) in chemical biology screens.
Materials/colloids: Highly hydrophobic diols can act as low-HLB amphiphiles in bespoke surfactant or nanoparticle coatings; adsorption on hydrophobic surfaces can be exploited in templating (general).
Practical tips:
Thoroughly dry glassware and solvents for moisture-sensitive transformations (silylations, acylations with acid chlorides).
For slow reactions on sterically hindered hydroxyls, use excess activating agent, mild heating (40–60 °C), or catalysts (DMAP for acylations).
Monitor by TLC with anisaldehyde or vanillin stains to visualize terpenoid cores.
Reaction Conditions
Typical conditions for common manipulations of hydrophobic triterpenoid diols (general literature/practice; adjust to your substrate and scale):
Acylation (ester formation):
Reagents: Acyl chlorides or anhydrides; catalysts such as DMAP (0.05–0.2 equiv) with Et3N.
Solvent: Anhydrous CH2Cl2, THF, or pyridine.
Temperature: 0 °C to RT; 2–12 h. Hindered OH may require 40–60 °C or excess reagent.
Silylation (TMS/TBDMS):
Reagents: TMS-Cl/imidazole (for GC derivatization), or TBDMS-Cl with imidazole.
Solvent: DMF, CH2Cl2, or acetonitrile; strictly dry.
Temperature: RT; 0.5–4 h. Quench and work up with aqueous NH4Cl.
Oxidation to carbonyls:
Reagents: Dess–Martin periodinane (DMP) or TEMPO/BAIB for selective oxidation when sterics allow.
Solvent: CH2Cl2 or acetonitrile; RT.
Notes: Monitor closely by TLC/MS; overoxidation or rearrangement can occur on crowded frameworks.
Carbamate formation (CDI route):
Reagents: CDI to form imidazolyl carbonate, then amine nucleophile.
Solvent: THF or CH2Cl2; RT to 50 °C.
Purification:
Normal-phase silica with hexanes/EtOAc gradients; visualize using anisaldehyde or vanillin stain with gentle heating.
For very nonpolar derivatives, add a small percentage of Et3N to suppress tailing.
Yields vary widely with substitution and sterics; pilot reactions (5–20 mg) are recommended before scale-up.
Safety and Handling
Product Data do not include GHS details for this item. Treat as you would a non-volatile, hydrophobic organic solid pending review of the SDS.
GHS/Classification: Not specified for this item; refer to SDS for authoritative classification, pictograms, and H-statements.
Primary hazards (general for class): Low volatility minimizes inhalation exposure; dust may cause mechanical irritation to eyes/respiratory tract. Hydrophobic solids may form slippery films. Combustible organic material.
PPE: Laboratory coat, safety glasses or goggles, and appropriate chemical-resistant gloves (e.g., nitrile). Use a dust mask/respirator if handling fine powders that may become airborne.
Engineering controls: Handle in a fume hood to avoid dust exposure and potential solvent vapors during dissolution. Employ local exhaust during weighing and transfers.
Incompatibilities: Strong oxidizers; avoid contact with strong acids/bases during storage. When preparing solutions, ensure complete dissolution before filtration to prevent clogging.
First aid (general): Skin—wash with soap and water; Eyes—rinse cautiously with water for several minutes and seek medical attention if irritation persists; Inhalation—move to fresh air; Ingestion—rinse mouth, do not induce vomiting; obtain medical attention per SDS guidance.
Spill response: Avoid dust generation. Collect mechanically; dampen with compatible solvent if needed. Dispose per institutional and local regulations.
Always consult the product SDS for definitive safety, toxicological, and disposal information before use.
Solvent Selection
Serratenediol, as a highly hydrophobic triterpenoid diol (literature, general), requires sufficiently nonpolar or amphiphilic organic media for dissolution.
Polarity/Miscibility profile (general):
Insoluble in water; wetting can be improved with a small percentage of organic co-solvent or surfactant systems.
Good solubility: CH2Cl2, CHCl3, toluene, THF, dioxane, DMSO.
Moderate solubility: EtOAc, acetone; solubility increases with temperature.
Limited in lower alcohols at RT; EtOH/IPA may be used warm or with co-solvent (DMSO or PEG-400) for bioassay stocks.
Stock solution practice (general):
Prepare concentrated stocks in DMSO (e.g., 10–50 mM) or CH2Cl2, then dilute into the working medium with vigorous mixing to avoid precipitation.
For aqueous systems, pre-dissolve in DMSO or ethanol and keep final co-solvent typically ≤1–2% v/v to maintain solubility without perturbing assays.
When to choose which solvent:
Spectroscopy/NMR: CDCl3 or C6D6 often give sharp signals; DMSO-d6 for hydrogen bonding insights.
Purification: Hexanes/EtOAc or toluene/EtOAc gradients on silica; slight addition of AcOH or Et3N can modulate tailing with polyols.
Derivatizations (acylation/silylation): Anhydrous CH2Cl2, THF, or pyridine are typical.
Always verify solubility empirically with your specific batch and temperature.
Storage and Reconstitution
Storage Conditions (product-specific): Room temperature (as provided in Product Data). Protect from moisture and prolonged light exposure. Keep container tightly closed.
Shipped In: Not specified for this item; refer to CoA/Spec Sheet.
Solid handling:
Store in the original, airtight container. For long-term retention of chromatographic purity, a desiccator or dry cabinet is recommended.
If the material is exceptionally nonpolar, static charge can cause powder cling—use antistatic measures and wide-bore spatulas during sampling.
Solution preparation (general guidance):
Prepare concentrated stocks in anhydrous DMSO or suitable organic solvent. If necessary, gently warm (≤40 °C) and/or sonicate to aid dissolution. Filter through PTFE if particulates remain.
Aliquot solutions to minimize headspace and avoid repeated freeze–thaw. For DMSO stocks, store at –20 °C to –80 °C for extended periods; allow to equilibrate to room temperature before opening to prevent moisture ingress.
Record solvent, concentration, and date on label; reassess purity by LC or NMR after extended storage.
Disposal: Follow institutional guidelines for non-halogenated or halogenated organic waste streams, depending on the solvent used.
Structure and Identity
Serratenediol is commonly referenced in the natural products literature as a serratene-type pentacyclic triterpenoid bearing two hydroxyl groups.
CAS: 2239-24-9 (product-specific)
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 (literature/context):
Core scaffold: Serratane triterpenoid — a rigid, fused pentacyclic hydrocarbon framework related to hopane/oleanane families but with the serratane ring fusion pattern.
Functional groups: Diol (two alcohols). Exact positions and stereochemistry of the hydroxyls vary by serratenediol isomer reported in literature; consult the CoA for the specific isomer supplied.
Stereochemistry: Multiple, densely substituted stereocenters typical of pentacyclic triterpenes; absolute configuration is scaffold-defined but not specified here for this item.
2D description in words: A compact, polycyclic, hydrophobic carbon skeleton composed of five fused rings with two hydroxyl substituents positioned on tertiary/secondary carbons; no heteroatoms other than the two oxygens from the alcohol groups.
Notes:
Nomenclature in the literature may distinguish positional isomers (e.g., 3,21-diol variants). Where isomerism matters for your application (spectroscopy, derivatization, or bioassay), verify identity against the item’s CoA and NMR data.
Synthetic Utility
Serratenediol offers a dense, stereodefined scaffold with two hydroxyl handles, making it a versatile platform in semisynthetic and derivatization chemistry (general literature guidance):
Protecting group chemistry: Install silyl ethers (TBDMS, TBS, TIPS) or esters (acetates, benzoates) selectively to orchestrate stepwise functionalization. Bulky silyl groups can differentiate primary/secondary/tertiary OH reactivity if positional isomers exist.
Upfield functionalization: Oxidize accessible alcohols to ketones/aldehydes (Dess–Martin, Swern), enabling formation of hydrazones/oximes or further Wittig/olifination steps, extending the framework.
Carbamate/carbonate formation: Convert OH groups to carbamates (e.g., with CDI + amine) or carbonates (e.g., with chloroformates) to probe electronic effects and stability.
Etherifications: Employ Williamson conditions where sterics allow, or Mitsunobu-type inversions on less hindered centers (recognizing the steric congestion common to triterpenes).
Late-stage diversification: Use radical or metal-catalyzed C–H functionalizations judiciously on the saturated core; selectivity often benefits from preinstalled directing groups.
Analytical leverage: Derivatize to TMS ethers for GC–MS confirmation of the core skeleton; NMR assignments benefit from differential protection to simplify overlapping signals.
These strategies enable library synthesis for SAR or materials screening without altering the inherent stereochemical integrity of the serratane core.
Target Specificity
Not applicable. This product is a small-molecule triterpenoid, not an antibody, probe, or biologic. No target-binding specificity, epitope, or isotype information is provided or implied for this item.
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