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.
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.
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
574.800 g/mol
XLogP3
7.700
Hydrogen Bond Donor Count
4
Hydrogen Bond Acceptor Count
6
Rotatable Bond Count
9
Exact Mass
574.423 Da
Monoisotopic Mass
574.423 Da
Topological Polar Surface Area
99.400 Ų
Heavy Atom Count
41
Formal Charge
0
Complexity
964.000
Isotope Atom Count
0
Defined Atom Stereocenter Count
14
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
Calcolatori di soluzioni
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Recensioni
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Application Protocols
No assay-specific validation data are provided for this item. The following are literature-based, general-use protocols for steryl glucosides:
Preparation of stock solutions:
Dissolve to 1–10 mg/mL in ethanol or isopropanol with gentle warming (40–50 °C) and sonication. Alternatively, use CHCl3:MeOH (2:1) for lipid film methods.
Lipid film hydration (for liposomes/rafts):
Combine phospholipids and clerosterol glucoside in CHCl3:MeOH, evaporate to a thin film under reduced pressure, dry under high vacuum ≥1 h, hydrate with warm buffer (e.g., HEPES saline, 50–60 °C) to 1–10 mg/mL total lipid, vortex, and extrude (100–200 nm filters).
Enzymatic hydrolysis assay:
Incubate 0.1–1 mM clerosterol glucoside with β-glucosidase in acetate buffer (pH 5.0) at 37 °C; sample over time; analyze aglycone release by LC–MS or GC–FID after saponification/derivatization.
LC–MS quantification:
Prepare calibration in MeOH with internal standard (e.g., deuterated steryl glucoside); inject on C18 with MeOH/H2O (0.1% formic acid or NH4Ac) gradient; detect by ESI+ ([M+Na]+) or APCI.
Adjust concentrations and conditions to your system; validate recovery and stability for your specific matrices.
Biological Roles
Literature/general background (no medical claims):
Steryl glucosides, including clerosterol glucoside, are ubiquitous plant membrane lipids formed by glycosylation of sterols at the 3β-hydroxy position via UDP-glucose:sterol glucosyltransferases.
Functional roles in plants and algae:
Membrane organization: contribute to lipid raft-like domains, influencing fluidity, permeability, and protein function.
Stress response: levels modulate under heat, cold, and pathogen challenge; acylated steryl glucosides act as storage/transport forms.
Cell wall and signaling interfaces: potential involvement in cell plate formation and trafficking; precursors to signaling oligos after hydrolysis.
Metabolic interconversions:
Reversible glycosylation between free sterol (e.g., clerosterol) and steryl glucoside; further acylation yields acyl steryl glucosides.
Hydrolysis by β-glucosidases releases the aglycone, impacting sterol homeostasis.
In microbes and food systems:
Occur in certain yeasts and plant-derived foods/oils; relevant to technological properties (e.g., foam stability, crystallization) in edible oils.
Note: These are general biological roles for the compound class; consult primary literature for species-specific pathways involving clerosterol glucoside.
Buffer Applications
This product is not a buffering reagent and does not establish defined pH ranges.
Practical guidance (general):
To introduce clerosterol glucoside into aqueous buffers, prepare a concentrated stock in ethanol, isopropanol, DMSO, or CHCl3:MeOH, then add slowly to warm buffer while vortexing. Incorporate carrier lipids (e.g., phosphatidylcholine) or mild detergents (e.g., 0.05–0.1% Triton X-100 or n-dodecyl maltoside) to avoid precipitation.
For liposome preparation, form a thin film from organic solution, then hydrate with the desired buffer above the lipid transition temperature with vigorous mixing or extrusion.
For pH control, use established buffers (e.g., phosphate, HEPES, Tris) appropriate to your biological system.
Green Alternatives
For handling steryl glucosides, greener solvent strategies can reduce chlorinated solvent use while maintaining performance.
Replace chloroform with ethanol, isopropanol, or 2-methyltetrahydrofuran (2-MeTHF) where feasible.
Use ethanol–water or isopropanol–water cosolvent systems for stock preparation followed by immediate dilution into buffers containing carrier lipids.
Comparison (general trends):
| Solvent/System | Greenness | Solubilization of Steryl Glucosides | Notes |
|---|---|---|---|
| CHCl3:MeOH (2:1) | Low | Excellent | Benchmark for lipid work; chlorinated waste. |
| Ethanol (absolute) | High | Moderate (improves with heat) | Biocompatible; easy removal. |
| Isopropanol | High | Moderate | Lower volatility; good for biological additions. |
| 2-MeTHF | Medium–High | Moderate | Bio-derived; check peroxides and stabilizers. |
| DMSO | Medium | Moderate | Aqueous miscibility; watch for precipitation on dilution. |
Process tips:
Warm green alcohols to 40–50 °C and sonicate to aid dissolution.
For lipid film methods, ethanol can substitute for chloroform in many cases; evaporate under reduced pressure and flush with inert gas to minimize oxidation.
Validate extraction and analytical methods when changing solvents to ensure recovery and response factors remain acceptable.
Pharmaceutical Uses
No therapeutic claims. The following are formulation-oriented, literature-based notes for research/manufacturing contexts:
Potential roles in delivery systems (general):
Membrane modifier in liposomal and lipid nanoparticle prototypes to adjust bilayer order and leakage profiles, analogous to free sterols but with increased headgroup polarity.
Excipient candidate in experimental solid dispersions or emulsions, where amphiphilicity aids stabilization.
Regulatory status: No pharmacopeial monograph is known for clerosterol glucoside; suitability for GMP use would require full qualification (identity, purity, residual solvents, elemental impurities, microbiological quality).
Compatibility:
Mixes with phospholipids and other neutral lipids; can reduce permeability of bilayers; may influence encapsulation efficiency and release.
Avoid strong acids/bases that hydrolyze the glycoside during processing.
Process considerations:
Prefer alcohol-based processes (ethanol, isopropanol) for greener handling; remove solvent under reduced pressure and apply nitrogen flushing to limit oxidation.
Validate stability during sterilization; sterile filtration may require co-solvent to maintain solubility.
Physical Properties
Item-specific (Product Data):
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Literature/general (for context; not item specifications):
Physical state: typically a white to off-white amorphous powder or microcrystalline solid for steryl glucosides.
Solubility profile: sparingly soluble in water; soluble in polar organic solvents such as methanol, ethanol (hot), and mixtures of chloroform/methanol (e.g., 2:1 v/v), and in DMSO to a limited extent; soluble in THF upon warming. Exact solubilities vary with isomer and sample history.
Partitioning: amphiphilic lipid; tends to associate with membranes, liposomes, and micelles; effective solubilization often requires alcohols or CHCl3/MeOH mixtures.
Thermal behavior: many steryl glucosides show high melting/softening points with possible decomposition before clear melting; avoid prolonged heating.
Spectroscopic notes: characteristic IR bands for O–H (broad), C–O (glycosidic), and sterol C=C; 1H/13C NMR diagnostic signals for β-glucose anomeric proton (~4.2–4.8 ppm, J1,2 ≈ 7–8 Hz) and sterol olefinic protons (~5–5.4 ppm).
Quality and Grades
Item-specific (Product Data):
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Interpreting quality for steryl glucosides (general guidance):
Purity assessment typically relies on HPLC/UPLC-ELSD or MS, supported by 1H/13C NMR. For lipid standards, reporting may include % area purity and isomeric composition of the aglycone (clerosterol vs related phytosterols).
Residual solvents and water: Karl Fischer and GC headspace are common controls; values are lot-specific (consult CoA).
Identity confirmation: HRMS (m/z [M+Na]+), specific rotation (for β-D-glucoside), and diagnostic NMR coupling of the anomeric proton (J1,2 ~7–8 Hz indicating β-linkage).
Stabilizers: Typically none are added to steryl glucosides. If any stabilizer/antioxidant were used, it would be disclosed on the CoA; none are specified for this item.
Suitability notes: For lipidomics or biophysical assays, select lots with narrow impurity profiles (low free sterol, minimal acylated steryl glucoside). Low-UV-absorbing solvents are recommended when purity is assessed by HPLC-UV.
Reaction and Applications
This compound is primarily used as a biochemical/lipid standard and as a functional amphiphile rather than as a classical reagent. However, the steryl glucoside functional groups enable useful transformations and applications.
Applications (literature/general):
Lipidomics standard: reference for quantifying steryl glucosides in plant or food matrices by LC–MS/ELSD.
Membrane biophysics: component in model membranes to study sterol–sugar effects on membrane order, raft formation, and phase behavior relative to free sterols.
Enzymology substrate: β-glucosidase assays (hydrolysis to clerosterol), sterol glycosyltransferase studies.
Materials: additive in lipid-based nanoparticles or vesicles to tune rigidity and permeability.
Transformations (general synthetic notes):
Acidic hydrolysis (MeOH–HCl, aq. HCl/heat) to release clerosterol (aglycone).
Enzymatic hydrolysis using β-glucosidases for mild deprotection.
Per-O-acylation (Ac2O/pyridine or acyl chlorides) to afford acylated steryl glucosides (ASGs), altering solubility and melting behavior.
Selective oxidation at C5/C6 of glucose (TEMPO/NaOCl) or at sterol double bonds (m-CPBA epoxidation) for derivatization studies.
Practical tips:
Ensure water-free conditions for acylations; use 4 Å molecular sieves if necessary.
For LC–MS, avoid plasticizers and use glassware; prepare fresh solutions to minimize adsorption losses.
Gentle warming (30–50 °C) and sonication aid dissolution; avoid prolonged high heat to limit glycosidic cleavage.
Reaction Conditions
General literature guidance for common manipulations of steryl glucosides (not product specifications):
Hydrolysis to aglycone:
Acidic: 0.5–2 M HCl in MeOH or aqueous MeOH, 40–70 °C, 1–6 h; monitor by TLC/HPLC. Neutralize and extract with hexane/EtOAc. Avoid overexposure to prevent sterol dehydration/side reactions.
Enzymatic: β-glucosidase (e.g., from almonds), pH 5–6 buffer, 30–40 °C; hours to overnight; yields clerosterol with minimal side reactions.
Per-O-acylation (analytical derivatization):
Ac2O/pyridine (5–20 equiv), rt–50 °C, 1–4 h; workup with MeOH then aqueous NaHCO3; purify by silica gel (elute with hexane/EtOAc gradients).
Epoxidation of sterol double bonds:
m-CPBA (1.0–1.5 equiv per C=C) in DCM, 0 °C to rt, 0.5–2 h; quench with Na2SO3; separate diastereomeric epoxides as needed.
Solvents and monitoring:
Solvents: CHCl3, MeOH, EtOH, DCM, THF depending on step; ensure dryness for acylations/oxidations.
Monitoring: TLC (hexane/EtOAc/MeOH), ELSD-HPLC for non-UV-active analytes, or LC–MS.
Peracetylation: often quantitative conversion; isolated yields 80–95% after workup.
Always optimize conditions for scale, purity targets, and aglycone stability.
Safety and Handling
Item-specific (Product Data):
GHS Classification: Not specified for this item; refer to SDS.
Signal Word: Not specified for this item; refer to SDS.
H-Statements: Not specified for this item; refer to SDS.
Pictograms: Not specified for this item; refer to SDS.
General laboratory guidance (literature/standard practice; defer to SDS as authoritative):
Hazard overview: Steryl glucosides are generally considered low volatility, low acute hazard laboratory chemicals but may cause irritation to eyes, skin, or respiratory tract as dusts.
PPE: lab coat, safety glasses, and nitrile gloves. Avoid generating dust; handle in a fume hood if powdering or weighing to minimize inhalation.
Handling: Use clean, dry tools. For solution prep, employ appropriate flammable-solvent precautions (if using methanol, ethanol, chloroform, or THF). Avoid strong oxidizers and strong acids/bases that can hydrolyze or degrade the glycoside.
First aid (summary):
Inhalation: move to fresh air; seek medical attention if symptoms persist.
Skin/eye contact: rinse with water for several minutes; remove contaminated clothing; seek medical advice if irritation continues.
Ingestion: rinse mouth; do not induce vomiting; obtain medical attention.
Fire safety: Organic solid; combustible. Use CO2, dry chemical, or foam on small fires. Combustion may produce CO/CO2.
Stability: Avoid excessive heat and prolonged exposure to moisture which may promote hydrolysis.
Solvent Selection
Clerosterol glucoside is an amphiphilic lipid. Solvent choice determines handling, stock preparation, and delivery to biological or materials systems.
Practical solvent choices (general guidance):
Chloroform:methanol (2:1 v/v): widely used for steryl glucosides; promotes dissolution and compatibilizes with lipid film formation and Bligh–Dyer/Folch workflows.
Methanol or ethanol: convenient, greener than chlorinated solvents; may require heating or sonication; solubility typically moderate.
Isopropanol: intermediate polarity; useful for cell-free systems and detergent-free reconstitutions; may need warming.
DMSO: limited to moderate solubility; miscible with aqueous buffers upon dilution but may precipitate; pre-warm and add slowly.
THF: dissolves steryl glucosides upon warming; compatible with polymer/lipid blend casting; peroxide formation risk in stored THF (use inhibitor-checked, freshly opened).
Polarity/miscibility (literature, general):
Amphiphilic with low aqueous solubility; forms micelles/vesicles with surfactants or phospholipids. Insoluble in pure water; dispersible via co-solvent or lipid carriers.
When to choose which:
Analytical prep (HPLC/MS standards): CHCl3:MeOH or MeOH.
Biological reconstitution: ethanol or isopropanol stocks added to warm buffer containing carrier lipids or mild detergents.
Thin films/liposomes: dissolve in CHCl3:MeOH, rotary evaporate to film, hydrate above Tm with buffer.
Storage and Reconstitution
Item-specific (Product Data):
Storage Conditions: Room temperature.
Shipped In: Not specified for this item; refer to CoA/Spec Sheet.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
General recommendations (literature/standard practice):
Long-term storage: Keep tightly sealed in an amber glass vial at ambient temperature, dry conditions, and protected from light. For multi-month storage, consider desiccation (silica gel) and inert gas blanket (nitrogen or argon) to minimize oxidative changes.
Stability: Stable as a dry solid under recommended conditions. Avoid prolonged exposure to moisture and heat to prevent glycosidic hydrolysis.
Reconstitution:
Prepare stocks at 1–10 mg/mL in ethanol, isopropanol, DMSO, or CHCl3:MeOH (2:1). Warm to 40–50 °C and sonicate if needed.
For aqueous use, add organic stock slowly to warm buffer with vigorous mixing; include carrier lipids or mild detergents to prevent precipitation.
Aliquoting: Prepare single-use aliquots to avoid repeated opening and moisture uptake. If preparing solutions, store at 2–8 °C and use within days to weeks; for CHCl3-containing solutions, minimize headspace and store under inert gas.
Research Use Note: For research use only.
Structure and Identity
Brief overview: Clerosterol glucoside is a plant steryl β-D-glucoside derived from the sterol clerosterol, featuring a glucopyranosyl moiety linked to the 3β-hydroxyl of the sterol nucleus.
Item-specific (Product Data):
CAS: 123621-00-1
CID: 91895415
InChIKey: 85454 (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/Computed (general reference, not item-specific specs):
Typical molecular formula for clerosterol 3-O-β-D-glucopyranoside is approximately C35H58O6 (derived from clerosterol + glucose − H2O).
Approximate formula weight ≈ 574.8 g/mol (computed from above formula).
Structural features (general chemistry knowledge):
Sterol core: tetracyclic cyclopentanoperhydrophenanthrene skeleton with a 3β-hydroxyl group.
Glycosidic linkage: β-D-glucopyranosyl at C-3 (3β-O-β-D-glucoside), forming a steryl glucoside.
Side chain: characteristic of clerosterol (a Δ5,22-dien plant sterol isomer); exact double-bond placement per clerosterol literature.
2D description in words: fused A/B/C/D rings (trans-decalin A/B) bearing a β-oriented O-glycosidic glucose at C3; an isooctyl-type side chain on C17; one or more double bonds in the sterol nucleus/side chain per clerosterol.
Synthetic Utility
Although primarily a biochemical standard, clerosterol glucoside has useful functional handles for synthesis and derivatization.
Functional group reactivity (general):
Glycosidic linkage: susceptible to acid- or enzyme-catalyzed hydrolysis to yield clerosterol and glucose.
Multiple alcohols (on glucose): amenable to selective protection/acylation (e.g., per-O-acetylation, benzoylation) enabling further glyco-derivatization.
Olefin(s) in sterol moiety: epoxidation, hydroboration–oxidation, or ozonolysis for side-chain mapping/modification.
3-position locked as glycoside: contrasts with free sterol where 3β-OH is available; hence reactivity shifts to sugar hydroxyls and double bonds.
Typical transformations:
Peracetylated clerosterol glucoside via Ac2O/pyridine (rt to 50 °C) to improve chromatographic behavior.
Enzymatic transglycosylation using retaining β-glucosidases or glycosynthases to alter the sugar moiety.
Selective deacylation or oxidation on sugar (TEMPO-mediated C6 oxidation) to prepare uronic-acid derivatives.
Retrosynthetic value:
Serves as a protected form of clerosterol for workflows requiring temporary masking of the 3β-OH while preserving sterol topology.
As a standard, facilitates structure–activity studies contrasting free sterol vs glycosylated forms in membranes.
Target Specificity
Not applicable. This product is a small-molecule lipid and is not an antibody, enzyme preparation, or affinity reagent.
Item-specific (Product Data): No target, clone, isotype, or species reactivity information is provided or relevant for this compound.
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