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Stockage & expédition
Room temperature Expédition . Consultez le COA spécifique au lot pour les spécifications exactes.
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Documents qualité
SDS, COA, fiche technique et fiche de spécifications disponibles au téléchargement. COA spécifique au lot accessible via la recherche par numéro de lot.
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Preuve documentaire
Cité dans 0 publications à comité de lecture couvrant la chromatographie, la synthèse organique et les réactions de couplage croisé.
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
428.700 g/mol
XLogP3
10.100
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
1
Rotatable Bond Count
0
Exact Mass
428.402 Da
Monoisotopic Mass
428.402 Da
Topological Polar Surface Area
20.200 Ų
Heavy Atom Count
31
Formal Charge
0
Complexity
741.000
Isotope Atom Count
0
Defined Atom Stereocenter Count
0
Undefined Atom Stereocenter Count
10
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 tested bioassay or immunoassay application protocols are provided for this item.
General preparation for analytical use (guidance):
Prepare a primary stock solution at 10–50 mg/mL in DMSO, chloroform, or toluene. Warm gently and sonicate if needed to fully dissolve.
For LC–MS: dilute the stock into acetonitrile or isopropanol-rich mobile phase; include a small percentage of isopropanol to aid ESI/APCI nebulization for highly nonpolar analytes.
For GC–MS: optional acylation (acetate) can improve volatility and peak shape; inject on a nonpolar column (e.g., 5% phenyl-methylpolysiloxane) with temperature programming.
Note: These are generic laboratory practices for hydrophobic small molecules. Adjust to your instrument and method requirements.
Biological Roles
General/literature context (no clinical claims):
Friedelanol is a plant-derived pentacyclic triterpenoid found in cuticular waxes, bark resins, and leaves across diverse taxa. It is biosynthetically related to hopanoids and other cyclized triterpenes formed from squalene/oxidosqualene via cyclase-mediated cascades.
Proposed ecological roles include contributions to cuticle hydrophobicity, barrier function against desiccation, and chemical defense. Its rigid, saturated framework and single hydroxyl group modulate membrane and surface properties of plant tissues.
In metabolomics/chemotaxonomy, friedelanol and its oxidized counterpart (friedelin) serve as markers for specific genera or extraction fractions (e.g., nonpolar hexane/chloroform extracts).
As a reference compound, it assists in developing and validating chromatographic methods for triterpenoid profiling (retention windows, ionization efficiency in APCI/ESI under neutral loss of water, where applicable).
Note: Biological roles and distribution are provided as general background. This product is supplied strictly for research use only, as indicated by the Product Data.
Buffer Applications
Not typically applicable. Friedelanol is a highly hydrophobic, water-insoluble small molecule and is not used to prepare aqueous buffers or as a buffering component.
Practical note: When introducing friedelanol into biological assays, prepare stock solutions in DMSO or ethanol and dilute into assay media with attention to final solvent percentage and use of solubilizers (e.g., nonionic surfactants) if required.
Green Alternatives
Greener handling of friedelanol focuses on solvent selection for dissolution, purification, and derivatization.
Comparison (general guidance):
Conventional vs greener choices:
Chlorinated solvents (CH2Cl2, CHCl3): high solvency but environmental/health concerns. Greener swaps include 2-MeTHF or CPME for many acylations/oxidations, and ethyl acetate for workups.
Aromatic hydrocarbons (toluene/benzene): toluene preferred over benzene; in some cases, p-xylene or heptane/isohexane mixtures can replace toluene while maintaining solubility.
Hexane: consider heptane/isoparaffins as lower-toxicity alternatives during chromatography.
Small comparison table (general):
CH2Cl2: excellent solubility; poor EHS profile; difficult to replace for very fast acylations—trial CPME/2-MeTHF.
2-MeTHF: good solvency, renewable origin, water separable; may require mild heating for complete dissolution.
CPME: broad compatibility, low peroxide formation, easy workup; similar elution strength to Et2O.
Ethyl acetate: greener eluent and extraction solvent; adjust with heptane to match Rf.
Operational tips:
Use solid-phase extraction (SPE) or dry-loaded flash to reduce solvent volumes during purification.
Minimize chlorinated solvent use to final analytical prep (e.g., CDCl3 for NMR) where alternatives are impractical.
Recover and recycle heptane/EtOAc fractions when feasible.
Pharmaceutical Uses
No pharmacopeial/excipient status or formulation grade is specified for this item; refer to CoA/Spec Sheet.
General research/manufacturing context (no therapeutic claims):
Employed as a reference standard in quality control of botanical raw materials and extracts containing friedelane-type triterpenoids.
Occasionally used as a hydrophobic model compound for studying solubilization strategies (e.g., cyclodextrin inclusion, lipid carriers) in pre-formulation research.
For solid-state studies, its rigid pentacyclic core can serve as a model for crystallization/thermal behavior of high-MW hydrophobes.
Important: This product is for research use only and is not intended for use in human or veterinary drugs or diagnostics.
Physical Properties
Item-specific physicochemical specifications (BP/MP, density, UV cutoff, elemental limits) are not listed in the Product Data for SKU F950262.
Melting point, boiling point, density, refractive index: Not specified for this item; refer to CoA/Spec Sheet.
Solubility (general/literature expectations for friedelane triterpenoid alcohols):
Practically insoluble in water; highly soluble in nonpolar and moderately polar aprotic organic solvents (e.g., chloroform, dichloromethane, toluene, benzene, hexanes) and soluble to sparingly soluble in hot alcohols (ethanol, isopropanol, methanol).
Soluble in DMSO; preparative stock solutions are commonly made in DMSO or chloroform for analytical use.
Lipophilicity (literature-based qualitative): very high logP consistent with a C30 triterpenoid scaffold bearing a single hydroxyl group.
pKa: the tertiary alcohol is non-acidic; no relevant pKa in aqueous media (literature/general knowledge).
Practical handling implications (general):
Expect waxy/solid behavior with a sharp melt only near its literature-reported MP; dissolution often benefits from gentle warming and sonication in suitable organic solvents.
Ensure solutions are water-free for moisture-sensitive derivatizations (e.g., acylation, Mitsunobu).
Quality and Grades
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/antioxidants: Not specified for this item; refer to CoA/Spec Sheet.
Guidance on quality interpretation (general):
For natural-product standards such as friedelanol, key quality attributes often include high assay purity (e.g., GC/LC ≥95–98%), low residual solvent content, and identity confirmation by NMR/HRMS. When provided by Aladdin, these appear on the CoA.
If designated as “analytical standard” or “reference material” grade (not specified here), expect enhanced documentation (chromatographic purity, identity spectra) suitable for method development and quantitative analysis (HPLC/GC, qNMR).
Low-UV background is generally not critical for this analyte, but baseline separation from co-eluting triterpenes is important. Verify chromatographic suitability with your own system and matrix.
For semisynthesis work, verify residual moisture and confirm that the material is free from oxidized congeners (e.g., friedelin) if your transformation is oxidation-sensitive.
Recommendation: Review the lot-specific CoA for assay, identity data (1H/13C NMR), and any residual solvent/water content prior to use in quantitative applications.
Reaction and Applications
Use-cases for friedelanol span reference standardization, phytochemical profiling, and semisynthetic derivatization at the hindered C-3 tertiary alcohol.
Analytical and reference uses:
Matrix marker and calibration standard in LC–MS/GC–MS profiling of plant waxes and resins; assists in authentication of botanicals containing friedelane-type triterpenoids.
Derivatization chemistry (general):
Esterification/acylation: The sterically hindered tertiary alcohol reacts with acid chlorides/anhydrides under activating conditions (e.g., DMAP catalysis or elevated temperature) to give friedelanyl esters (useful for lipophilicity tuning and GC volatility enhancement).
Oxidation: Conversion to friedelin (ketone) via chromium(VI)-based oxidants or hypervalent iodine reagents has been reported (literature); milder methods (e.g., DMP) may require extended times due to steric congestion.
Mitsunobu-type substitution: Despite tertiary nature, specialized variants enabling dehydration–capture or intramolecular cyclizations are used; classical SN2 Mitsunobu is not applicable at tertiary centers but can promote formation of derivatives via rearrangements under carefully chosen conditions.
Dehydration/elimination: Strong acids (e.g., H2SO4, TsOH) induce olefin formation on the A-ring; products can be hydrogenated or further functionalized.
Carbon–carbon frameworks: Friedelanol serves as a robust, sterically defined scaffold for late-stage diversification and probe design.
Practical tips:
Ensure anhydrous solvents and inert atmosphere for moisture-sensitive transformations.
Monitor by TLC in nonpolar systems (e.g., hexane/EtOAc 9:1 → 7:3); stain with anisaldehyde or vanillin for triterpenes.
Because of high hydrophobicity, slow diffusion in reaction media can limit rates; vigorous stirring and moderate heating help.
Reaction Conditions
Typical laboratory conditions reported in the literature for transformations of friedelanol-like tertiary alcohols (general guidance; optimize for your system):
Acetylation/Acylation:
Reagents: Ac2O (3–5 equiv) or acid chloride (2–3 equiv), DMAP (0.1 equiv), pyridine or CH2Cl2 as solvent.
Conditions: 0 °C to reflux, 1–16 h. Monitor by TLC (hexane/EtOAc). Workup: aqueous bicarbonate, then brine.
PCC (2–3 equiv) in CH2Cl2, rt, 4–24 h, or Jones oxidation (CrO3/H2SO4, acetone, 0–25 °C, 0.5–2 h). Alternative: DMP (2–3 equiv), CH2Cl2, rt, 6–24 h.
Dehydration:
Reagents: TsOH (cat.) or POCl3/pyridine.
Conditions: toluene or CH2Cl2, 0 °C to reflux, 1–6 h; may give mixtures of alkenes—separate by chromatography.
Protection (silylation is uncommon for tertiary OH but possible with strong silylating agents):
Reagents: TMSOTf or TBDMSCl with imidazole/DMF (harsh; assess compatibility).
Analytical monitoring:
TLC stains: anisaldehyde or vanillin; triterpenoids respond well with heating.
NMR: CDCl3 preferred; characteristic tertiary C–O signal in 13C NMR typically ~70–75 ppm (literature-general range).
Note: These are literature-style conditions for similar substrates; validate on small scale before scale-up.
Safety and Handling
Hazard classification and labeling are not provided in the Product Data for this item.
GHS Classification: Not specified for this item; refer to SDS.
Signal Word / H-Statements / Pictograms: Not specified for this item; refer to SDS.
General laboratory safety guidance (non-item-specific, defer to SDS for authority):
PPE: laboratory coat, safety glasses, and appropriate gloves (e.g., nitrile). Avoid inhalation of dust and contact with skin/eyes.
Handling: Treat as a hydrophobic organic solid. Avoid generating dust; use in a fume hood when weighing or preparing solutions in volatile organic solvents (e.g., chloroform, DCM, toluene).
Incompatibilities (general): strong oxidizing agents (may oxidize the alcohol or hydrocarbon framework under forcing conditions). For reactions employing strong acids (e.g., conc. H2SO4), dehydration/cationic rearrangements may occur.
First aid (general):
Inhalation of dust/solvent vapors: move to fresh air; seek medical attention if symptoms persist.
Skin/eye contact: rinse with water for at least 15 minutes; remove contaminated clothing.
Ingestion: rinse mouth; do not induce vomiting; seek medical advice.
Spill/cleanup: Avoid dust; collect solid mechanically. For solution spills, absorb with inert material. Dispose of waste according to local regulations.
Always consult the Aladdin SDS for SKU F950262 for authoritative safety and handling requirements.
Solvent Selection
Friedelanol is a highly lipophilic, neutral triterpenoid alcohol. Solvent choice determines practicality in weighing, transfer, and derivatization.
Polarity/miscibility class: Nonpolar to weakly polar solute; favors nonpolar or moderately polar organic solvents.
Good with warming/sonication: ethanol, methanol, isopropanol, acetonitrile (variable), ethyl acetate.
Poor: water and aqueous buffers.
Stock solution practices: 10–50 mg/mL in DMSO, chloroform, or toluene for analytical uses; filter if necessary to remove particulates.
When to choose specific solvents:
Purification/flash chromatography: hexane/ethyl acetate or toluene/EtOAc gradients for resolution from other triterpenoids.
Acylations/oxidations: use dry, aprotic media (CH2Cl2, toluene, THF, 2-MeTHF) under inert atmosphere to limit moisture.
NMR: CDCl3 is typically preferred; C6D6 offers improved dispersion of upfield methyl signals.
Comparison note:
Versus sterol-like polyols, friedelanol’s single tertiary OH reduces hydrogen-bonding; thus, it dissolves better in nonpolar solvents than many polyhydroxylated triterpenes.
Storage and Reconstitution
Storage Conditions (item-specific): Room temperature (from Product Data).
Shipped In: Not specified for this item; refer to CoA/Spec Sheet.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
General storage guidance:
Keep container tightly closed in a dry, well-ventilated place. Protect from prolonged exposure to heat and direct sunlight. Use desiccant if ambient humidity is high.
Avoid repeated opening that may introduce moisture or contaminants, especially before moisture-sensitive derivatizations.
Reconstitution/preparation of solutions (guidance):
Prepare concentrated stock solutions in DMSO, chloroform, toluene, or ethanol. Gentle warming (30–50 °C) and sonication aid dissolution.
For biological assays, dilute organic stocks into media slowly with vigorous mixing to prevent precipitation. Keep final DMSO/EtOH content low (commonly ≤0.5–1% v/v) and consider solubilizers if needed.
For long-term solution storage, prefer amber vials under inert gas at 2–8 °C to limit oxidative changes; solid form is generally more stable at room temperature.
Research Use: For research use only (from Product Data).
Structure and Identity
Friedelanol (friedelan-3β-ol) is a pentacyclic triterpenoid alcohol of the friedelane series, commonly isolated from plant cuticular waxes and resins.
SKU: F950262
CAS: 5085-72-3 (item-specific)
InChIKey (from Product Data): 414110 (as provided; refer to CoA/SDS for full identifier)
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):
Pentacyclic, fully saturated hydrocarbon framework (friedelane skeleton) with a single tertiary alcohol at C-3 in the β-orientation.
Multiple quaternary carbons and angular methyl groups typical of hopane/friedelane triterpenes; no heteroatoms besides the C-3 hydroxyl.
Stereochemically rich: numerous defined stereocenters that impart a rigid, lipophilic, bowl-shaped 3D topology.
2D depiction in words: five fused carbocyclic rings (A–E), with a hydroxyl group at the bridgehead-like C-3 position on ring A, and methyl substituents distributed at ring junctions.
Notes:
Item-specific identifiers not provided above should be confirmed from the product CoA/Spec Sheet.
Friedelanol is distinct from friedelin (the corresponding C-3 ketone).
Synthetic Utility
Friedelanol provides a sterically congested, oxidation-state-rich platform for method development and late-stage diversification.
Key functional element:
A single tertiary alcohol on a rigid pentacyclic skeleton.
Acylation and carbamate formation to tune lipophilicity and volatility (useful for GC analysis and probe synthesis). Reagents: acid chlorides/anhydrides with DMAP or Lewis acids; CDI or triphosgene for carbamates with amines.
Oxidation to the corresponding ketone (friedelin) with Jones reagent, PCC, PDC, or DMP (longer times due to sterics). Followed by further chemistry at C-3 (e.g., Wittig-like methylenation after hydrazone formation from the ketone, in multistep sequences).
Dehydration to form isomeric alkenes under strong Brønsted or Lewis acid conditions; subsequent hydrofunctionalization (hydroboration–oxidation, epoxidation) introduces new handles.
Cationic rearrangements under superacid/Lewis acid conditions to access alternative skeletons, enabling structure–activity relationship (SAR) libraries.
Retrosynthetic value:
Serves as a chiral, conformationally locked scaffold to orient functional groups in 3D space; valuable in designing probes or materials where shape persistence is desired.
Reactions may be diffusion-limited; ensure efficient mixing and consider higher temperatures (within stability limits).
Target Specificity
Not applicable. This product is a small-molecule triterpenoid, not a biological macromolecule or affinity reagent. No antigen/epitope or species reactivity applies.
Foire aux questions
How should this product be stored?
Store at room temperature.
What are the CAS number, molecular formula and molecular weight?
The CAS Number is 5085-72-3. InChIKey XCDQFROEGGNAER-VYFOYESCSA-N.
What documentation is provided?
Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.
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