This compound belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24.
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.
Certificati (CoA, COO, BSE/TSE e tabella di analisi)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Proprietà chimiche e fisiche
Peso molecolare
448.700 g/mol
XLogP3
7.800
Hydrogen Bond Donor Count
3
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
6
Exact Mass
448.392 Da
Monoisotopic Mass
448.392 Da
Topological Polar Surface Area
60.700 Ų
Heavy Atom Count
32
Formal Charge
0
Complexity
663.000
Isotope Atom Count
0
Defined Atom Stereocenter Count
11
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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Recensioni
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Application Protocols
No manufacturer-validated application protocols are provided for this item. The following general workflows (literature/practice) can aid use in common settings:
Preparation of stock solutions:
Dissolve in DMSO at 10–50 mM or in ethanol at 1–10 mg/mL. Warm to 30–40 °C and sonicate if needed. Filter through 0.22 μm PTFE for sterile applications.
LC–MS sample preparation (lipidomics):
Spike internal standard, extract lipids with MeOH/MTBE or MeOH/CHCl3, dry under N2, reconstitute in isopropanol/ACN/H2O (2:1:1). For improved ionization, analyze as acetate or after derivatization (e.g., TMS for GC–MS).
Derivatization for GC–MS:
React with BSTFA + 1% TMCS, 60 °C, 30 min. Inject in splitless mode on low-polarity column.
Solid-phase handling:
Minimize adsorption losses by pre-wetting glassware with solvent and adding small amounts of alcohol to eluents. Use silanized vials if working at low ng levels.
These are general suggestions only. Validate and optimize conditions for your specific instrumentation and sample matrix.
Biological Roles
Literature context (for reference; not product claims):
Structural class: a phytosterane derivative (stigmastane core) with additional hydroxylations at 3β, 5α, and 6β. Stigmastane sterols are plant analogs of animal sterols (cholestane series).
Potential occurrence: tri-hydroxylated steranes can arise from oxidative metabolism of plant sterols (e.g., sitostane/stigmastane backbones) in plant tissues or during processing/autooxidation of phytosterol-rich matrices.
Biophysical properties: additional hydroxyls enhance hydrogen bonding with lipid headgroups, potentially affecting membrane ordering and phase segregation in model bilayers relative to sitosterol or cholesterol.
Biotransformations: enzymes that act on sterols (dehydrogenases, oxygenases) may interconvert alcohol and ketone functionalities at C3 and vicinal positions; however, specific enzymatic pathways for the 3β,5α,6β-triol of stigmastane are not comprehensively mapped in the literature.
Use in research:
Serves as a reference standard in lipidomics and sterol oxidation studies.
Useful probe for studying how sterol polyhydroxylation influences membrane interactions and protein binding (e.g., sterol-sensing domains) in vitro.
Note: This product is for research use only. No biological activity or clinical utility is implied.
Buffer Applications
Not typically applicable. Stigmastane-3β,5α,6β-triol is a hydrophobic small molecule and is not used to prepare buffering systems.
Practical note: For assays requiring aqueous media, prepare concentrated stocks in DMSO or ethanol and dilute into buffered solutions with surfactants (e.g., 0.01–0.1% Tween-80) or cyclodextrins to aid dispersion. Maintain final organic co-solvent typically ≤1–2% v/v to limit perturbation of biological systems.
Green Alternatives
Although the compound itself is not replaceable, greener choices can be made for its handling and transformations.
Greener solvent choices for common operations (literature guidance):
Dissolution and workup
Prefer ethanol or isopropanol over chlorinated solvents when feasible (warming and sonication may be required).
Ethyl acetate or 2-MeTHF can substitute for DCM/CHCl3 in many extractions and chromatographic separations.
Protection/acylation steps
Use greener acylation media (EtOAc or Me-THF) with catalytic DMAP instead of pyridine/DCM systems when possible.
Oxidations
Replace chromium(VI) reagents (PCC, Jones) with catalytic TEMPO/bleach (NaOCl) or PIDA-mediated oxidations in aqueous-organic biphasic systems to minimize heavy metal waste.
Small comparison (illustrative; not item specifications):
DCM/CHCl3: excellent solvency; high environmental impact and safety concerns.
EtOAc/2-MeTHF: good solvency for sterol triols; lower toxicity, biodegradable; may require slightly higher temperatures.
Ethanol: renewable and low-toxicity; slower dissolution and possible crystallization on cooling.
Process tips:
Minimize solvent volumes via concentrated stock solutions and micro-scale workflows.
Recycle silica and use greener eluents (heptane/EtOAc, heptane/IPA) for flash chromatography of polyols.
Pharmaceutical Uses
No pharmacopeial grade or excipient status is specified for this product; refer to the CoA/Spec Sheet. The following are general, non-clinical considerations for sterol derivatives in formulation science (literature context):
Role in formulations: Sterols and polyhydroxylated steranes can modify membrane rigidity and are sometimes used in research formulations to tune liposome stability, permeability, and phase behavior. Triols may influence bilayer hydration and packing more strongly than mono-ols.
Solubilization strategies: inclusion complexes with cyclodextrins (e.g., HP-β-CD) or incorporation into lipid nanoparticles/liposomes can enhance aqueous handling of hydrophobic steranes in research settings.
Analytical control: For any use in pre-formulation studies, characterize polymorphism and solid-state form (XRPD/DSC) and verify residual solvent content if produced by solvent crystallization.
This information is provided solely for research/formulation development context. No therapeutic or clinical claims are made for this product.
Physical Properties
Item-specific physical 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 properties (for reference; not item specifications):
State: solid, waxy/crystalline steroidal triol typical of phytosterol derivatives
Solubility: practically insoluble in water; soluble in chlorinated solvents (e.g., CHCl3), moderately soluble in alcohols (MeOH/EtOH) and polar aprotics (DMSO, DMF); increased solubility upon gentle warming or with co-solvents/surfactants.
LogP: expected high (literature sterane triols logP often >5), reflecting strong hydrophobicity with limited H-bond donor count of three.
UV/Vis: no strong chromophores; weak end absorption below ~210–220 nm typical of saturated steranes.
Melting range: steroidal triols often melt in the ~150–220 °C range depending on stereochemistry and purity; specific value for this isomer not established in common references.
Note: Use literature values as qualitative guidance only. For batch-specific specifications (mp, elemental analysis, water, residual solvents), consult the item’s CoA/Spec Sheet.
Quality and Grades
Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/inhibitors: Not specified for this item; refer to CoA/Spec Sheet.
Context and guidance (general):
For small-molecule library members like steroidal triols, CoA typically documents identity confirmation (NMR, MS), purity by HPLC/GC, and occasionally water content (KF) and residual solvents. In the absence of a listed grade, assume research-use reagent quality suitable for discovery chemistry and analytical standards.
UV transparency is usually not a constraint for steranes (no strong chromophores). If using for HPLC quantitation, prefer batches with HPLC purity ≥95% and well-resolved impurity profiles.
If chiral/stereodefined isomerism is critical (3β,5α,6β configuration), verify stereochemical integrity by 1D/2D NMR and optical rotation when available on the CoA. Diastereomeric impurities can co-elute; orthogonal methods (qNMR) are recommended for exact assay.
Metal content, peroxides, and specific trace limits are typically not specified for non-coordinating steroidal solids. If your application is catalysis-sensitive, request ICP-MS data.
Please refer to the product’s CoA/Spec Sheet for definitive grade, assay, analytical methods, and impurity limits for this SKU.
Reaction and Applications
As a stereodefined phytosterane triol, Stigmastane-3β,5α,6β-triol is valuable both as a reference standard and as a multifunctional scaffold in steroid chemistry.
Applications (literature/general):
Analytical/reference: standard for profiling phytosterol oxidation products and triols in plant matrices and food lipidomics by LC–MS/GC–MS (after derivatization such as TMS ethers or acetates).
Structure–property studies: evaluation of hydrogen-bonding, phase behavior, and membrane-mimetic interactions of sterols with additional hydroxylation.
Synthetic intermediate: three hydroxyl handles enable selective protection/deprotection sequences to access oxo-, acyl-, and ether-modified stigmastane derivatives.
Typical reactions on this scaffold:
Selective acylation: Ac2O or acyl chlorides with bases (pyridine/DMAP) to give mono-, di-, or tri-acetates; kinetic control can favor C3-O acylation.
Silylation: TBS-Cl or TBDPS-Cl with imidazole/DMF for orthogonal protection (C3-O often most reactive).
Oxidation: Swern or PCC to convert 3° alcohol at C3 (actually secondary) to ketone; 5α/6β vicinal diol can be oxidatively cleaved (NaIO4) if transformed to open-chain analogs is desired; on-ring periodate cleavage is typically limited—prefer TEMPO/bleach for selective oxidation.
Etherification/esterification: Mitsunobu (DEAD/PPh3) to invert configuration selectively at accessible alcohols (usually C3-OH), or carbonate formation for labeling.
Practical tips:
Maintain anhydrous, oxygen-limited conditions for sensitive transformations; include antioxidants (e.g., BHT) if storing solutions.
Chromatograph with small percentages of alcohol in eluent to prevent tailing due to multiple OH functions.
Reaction Conditions
General literature guidance for common transformations of sterane triols (conditions are examples; optimize for your system):
Selective acylation (favoring C3-OH):
Reagents: Ac2O (1.2–1.5 eq), catalytic DMAP (5–10 mol%), pyridine or Et3N, CH2Cl2 or EtOAc, 0–25 °C, 1–3 h. Monitor by TLC (EtOAc/heptane). Typical yields: 70–90% for monoacetates with controlled stoichiometry.
Global acylation to triacetate:
Reagents: Ac2O (excess), pyridine, rt to 40 °C, 2–6 h. Yields often >85%.
Silylation (TBS protection):
Reagents: TBS-Cl (3.0 eq), imidazole (6.0 eq), DMF, rt to 50 °C, 2–12 h. Sequential or one-pot protections can be tuned by reagent addition order. Typical isolated yields per step: 70–85%.
Oxidation of C3-OH to ketone:
Swern: (COCl)2/DMSO, −78 °C, then Et3N; DCM solvent. 65–90%.
DMP (Dess–Martin): DCM, rt, 1–3 h; 75–95%.
TEMPO/BAIB or TEMPO/NaOCl (pH ~9): biphasic CH2Cl2/H2O, 0–25 °C; 60–85% (minimizes heavy metals).
Mitsunobu inversion (at C3 preferentially):
Reagents: DEAD or DIAD, PPh3, R–CO2H or phenol, THF/DMF, 0–25 °C. 50–80% with careful control; over-reaction possible at other OH sites.
Derivatization for GC–MS analysis:
BSTFA + 1% TMCS, 60–70 °C, 30–60 min to form TMS ethers of all OH groups; improves volatility and chromatographic behavior.
Notes:
Use mild conditions to preserve ring integrity; avoid strong mineral acids/bases that can cause dehydration/rearrangements.
Include small alcohol in chromatographic eluents to reduce tailing and improve recovery of polyols.
Safety and Handling
GHS classification (item-specific): Not specified for this item; refer to SDS.
Signal word / H-statements / pictograms: Not specified for this item; refer to SDS.
General safety guidance for steroidal triols (literature/good practice):
Expected hazards: Low volatility solid; may cause skin/eye irritation. Avoid inhalation of dust and contact with skin/eyes.
Personal protective equipment: laboratory coat, safety glasses, and appropriate gloves (e.g., nitrile). Use dust control (weighing in a hood) and avoid aerosol generation.
Handling: Hygroscopic uptake is usually minimal for hydrophobic sterols, but triols can retain solvents; keep containers tightly closed. Use clean, dry tools to prevent contamination.
Incompatibilities: Strong oxidizers (risk of exothermic reaction), strong acids/bases (can promote dehydration/fragmentation). Avoid prolonged exposure to elevated temperatures and light that may induce oxidation.
First aid overview: If on skin/eyes, rinse with water for several minutes; remove contaminated clothing. If inhaled, move to fresh air. If ingested, rinse mouth. Seek medical attention if symptoms persist.
Fire safety: Combustible organic solid. In case of fire, use dry chemical, CO2, or foam. Thermal decomposition may produce CO/CO2.
Always consult the official SDS for authoritative hazard classification, first aid measures, and disposal guidance for this specific product.
Solvent Selection
This compound is a hydrophobic sterane triol with three hydroxyl groups. It dissolves best in moderately polar organic solvents and poorly in water.
Moderate: ethanol/isopropanol (often requires warming and sonication), acetonitrile (limited).
Poor: water, hexanes (triol reduces solubility vs hydrocarbons).
Stock solution tips:
Prepare concentrated stocks in DMSO (e.g., 10–50 mM) or CHCl3 for analytical work; for biological assays, DMSO or ethanol stocks diluted into buffer with surfactant (e.g., 0.1% Tween-80) can improve dispersion.
Gentle warming (30–40 °C) and brief sonication assist dissolution. Avoid prolonged heating to reduce oxidation risks.
Selection relative to alternatives:
For preparative chromatography, use CHCl3/MeOH or hexanes/EtOAc gradients; the triol elutes more polar than parent steranes.
For NMR, CDCl3 typically affords sharp signals; DMSO-d6 may be needed if solubility in CDCl3 is limited.
Small comparison (literature expectation):
CHCl3: rapid dissolution; non-protic, good for recovery.
EtOH: greener, but slower to dissolve; may crystallize on cooling.
DMSO: excellent solvating power; leaves high-boiling residue—plan an aqueous workup or triturate to remove.
Storage and Reconstitution
Item-specific storage/shipping:
Storage Conditions: Room temperature (per Product Data).
Shipped In: Not specified for this item; refer to CoA/Spec Sheet.
Stability guidance (general):
Store tightly closed in a dry, inert environment, protected from light. Although saturated steranes are relatively robust, polyhydroxylated derivatives can slowly oxidize; minimize exposure to air and elevated temperatures.
For long-term storage of solutions, keep under inert gas (N2/Ar) at 2–8 °C where feasible, and consider adding a trace antioxidant (e.g., BHT) if compatible with downstream use.
Reconstitution (general laboratory practice):
Prepare concentrated stocks in DMSO (10–50 mM) or ethanol (1–10 mg/mL). Warm gently (30–40 °C) and sonicate to aid dissolution. Avoid water as a primary solvent; for aqueous applications, dilute organic stocks into buffer containing a solubilizer (surfactant or cyclodextrin) with vigorous mixing.
Avoid repeated freeze–thaw of solutions; aliquot stocks to single-use vials. Solid material can be subdivided and stored in amber containers to limit photodegradation.
Always consult the product’s CoA/Spec Sheet and SDS for definitive handling and storage instructions for this SKU.
Structure and Identity
Stigmastane-3beta,5alpha,6beta-triol is a saturated phytosterane (C29) triol featuring the stigmastane framework with three secondary alcohols at C3 (β), C5 (α), and C6 (β).
Item-specific identifiers from Product Data:
CAS: 20835-91-0
InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
SKU: S1025661
Category: Small molecules and compound library (可售 / 小分子和化合物库)
Literature/computed identity (for reference; not item specifications):
Common name variants: 3β,5α,6β-trihydroxystigmastane; stigmastane triol (3,5,6-triol)
Molecular formula (literature): ~C29H52O3
Molecular weight (literature): ~448.7 g/mol
Structural class: tetracyclic cyclopentanoperhydrophenanthrene (sterane) nucleus with C24-ethyl side chain (stigmastane) and three vicinal hydroxyls on ring B/A edge (3β–5α–6β).
2D structural description (literature): four fused saturated rings (A–D) in the steroid backbone; a β-oriented OH at C3 on ring A; adjacent 5α and 6β hydroxyls on ring B in trans relationship; an eight-carbon side chain at C17 including an ethyl substituent at C24 characteristic of stigmastane.
Synthetic Utility
Stigmastane-3β,5α,6β-triol is a versatile, stereochemically rich scaffold for target-oriented and diversity-oriented synthesis in the sterane family.
Key features and transformations (literature/general):
Functional handles: three secondary alcohols at defined stereocenters (3β, 5α, 6β) enable selective derivatization. The C3-OH is typically the most reactive due to electronic/steric environment on ring A.
Protection strategies: orthogonal protection with TBS (bulkier, more robust) at less hindered positions and acetyl or benzoyl groups at the most reactive site facilitates sequential functionalization.
Oxidation state edits: C3-OH → ketone via Swern, DMP, or TEMPO/BAIB systems; subsequent stereoselective reductions (e.g., CBS, L-Selectride) can set alternative configurations.
Vicinal diol chemistry (5α,6β): formation of cyclic carbonates, sulfates, or selective acylations affords conformational probes; careful selection of catalysts (DMAP vs pyridine) controls regioselectivity.
Late-stage diversification: carbonate/urethane installation for bioconjugation, etherification (Williamson or Mitsunobu) to introduce reporter groups, and esterification to modulate lipophilicity.
Retrosynthetic value: serves as an advanced intermediate to access 5–6 functionalized steranes (e.g., epoxides, diols, ketones) without modifying the C17 side chain of the stigmastane series.
Purification guidance:
Use normal-phase silica with heptane/EtOAc containing 0.5–2% alcohol to curb tailing; alternatively, reverse-phase C18 with MeOH/H2O (with 0.1% formic acid) for analytical separations after derivatization.
Target Specificity
Not applicable. This product is a small-molecule sterane triol, not an antibody, enzyme, or ligand with defined biological target specificity validated by the manufacturer. If used as a probe in biochemical assays, any target interactions should be established experimentally by the end user.
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