This compound belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. These are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol.
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
320.420 g/mol
XLogP3
2.400
Hydrogen Bond Donor Count
4
Hydrogen Bond Acceptor Count
6
Rotatable Bond Count
11
Exact Mass
320.22 Da
Monoisotopic Mass
320.22 Da
Topological Polar Surface Area
99.400 Ų
Heavy Atom Count
22
Formal Charge
0
Complexity
275.000
Isotope Atom Count
0
Defined Atom Stereocenter Count
5
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 protocols are provided for this SKU. The product is not an antibody or assay kit; therefore, applications like WB, IHC, IF, or FC do not apply.
General (non-validated) protocol guidance for laboratory use (literature):
Preparation of stock: dissolve the required mass in deionized water to desired concentration (e.g., 10% w/v). Gentle warming (≤40 °C) and stirring accelerate dissolution. Avoid strong acids/bases.
Membrane protein extraction: suspend membrane fraction in neutral buffer (e.g., 50 mM Tris, 150 mM NaCl, pH 7.5) containing 0.5–2% decyl glucoside; incubate 30–60 min at 4–25 °C with gentle mixing; clarify by centrifugation.
Detergent removal: dialyze against large volumes of buffer, adsorb with polystyrene beads, or dilute below CMC followed by ultrafiltration.
These are general literature practices and must be optimized for your system. Item-specific, tested application parameters: Not specified for this item; refer to CoA/Spec Sheet.
Biological Roles
Decyl glucoside, alpha- does not occur as a natural metabolite; it is a synthetic nonionic surfactant composed of a glucose headgroup and a decyl tail. Its relevance in biological workflows is functional rather than metabolic.
Functional roles in biochemistry (literature):
Membrane protein solubilization: nonionic glucosides can extract membrane proteins with reduced denaturation compared to ionic surfactants; the decyl chain offers intermediate hydrophobicity versus octyl and lauryl analogs.
Stabilization of protein complexes: at sub-CMC to modest above-CMC levels, can minimize aggregation by weakly coating hydrophobic patches without strongly disrupting tertiary structure.
Lipid vesicle manipulation: facilitates formation or disruption of liposomes and model membranes; useful in reconstitution and transport assays.
Enzyme assays: can reduce nonspecific adsorption of hydrophobic substrates or products to plastics/glass and enhance apparent solubility.
Selectivity considerations:
Being nonionic, it minimally perturbs ionic strength and pH of buffers, reducing interference in many enzymatic systems compared to ionic surfactants.
Gentle conditions (neutral pH, moderate temperature) help preserve the glycosidic bond and maintain consistent surfactant behavior during biological experiments.
Caveats:
Even mild surfactants can inactivate sensitive enzymes or disrupt weak protein–protein interactions; titration of concentration (often 0.01–1% w/v) is recommended.
Removal strategies include dilution below CMC, dialysis, adsorbents, or precipitation of target complexes.
No medical or clinical claims are implied; this product is for research use only.
Buffer Applications
As a nonionic surfactant, α-decyl glucoside is not a buffering agent, but it is frequently incorporated into buffer systems to modulate solubilization, protein stability, and membrane interactions.
Common buffer uses (literature/general):
Lysis and extraction buffers: 0.05–2% (w/v) in neutral buffers (e.g., 20–50 mM Tris, HEPES, or phosphate, pH 7.0–8.0) for membrane protein extraction or gentle cell lysis when ionic detergents are too harsh.
Wash buffers for affinity/IMAC/chromatography: 0.01–0.2% to reduce nonspecific binding and maintain solubility of hydrophobic proteins/complexes.
Reconstitution of lipids and proteoliposomes: above-CMC concentrations to solubilize lipids, followed by detergent removal (dialysis, Bio-Beads, dilution) to reform bilayers.
Enzyme assay buffers: sub-CMC amounts (0.001–0.05%) to minimize surface adsorption without significantly altering kinetic parameters.
Practical guidance:
Prepare fresh working solutions; adjust ionic strength gently (e.g., 50–150 mM NaCl) to tune micelle characteristics. Avoid strong acids/bases that can hydrolyze the glycosidic bond over time.
Temperature affects micellization and viscosity; keep consistent between runs.
Detergent can interfere with certain colorimetric/fluorometric assays (e.g., some dye-binding protein assays); verify compatibility or use detergent-tolerant kits.
Item-specific buffer details for this SKU (pH range, stabilizers, assay compatibility): Not specified for this item; refer to CoA/Spec Sheet.
Green Alternatives
Alkyl glucosides, including α-decyl glucoside, are often considered greener surfactants due to renewable feedstocks (glucose and fatty alcohols) and favorable aquatic profiles compared to some traditional nonionics.
Comparison (general literature):
Feedstock and renewability:
Decyl glucoside: derived from glucose and fatty alcohols (often plant-based). Renewable carbon content is high.
Ethoxylated nonionics (e.g., PEG-based): derived partly from ethylene oxide (petrochemical), with worker-safety considerations during manufacture.
Biodegradability and aquatic impact:
Decyl glucoside: readily biodegradable in standard tests; breakdown to sugars and fatty alcohol derivatives.
Some legacy nonionics: variable biodegradation; potential for persistent metabolites.
Process/usage advantages:
Enables aqueous media for synthesis and cleaning, reducing VOC emissions.
Lower toxicity profile vs many ionic surfactants, aiding EHS goals.
Tradeoffs and considerations:
Purity/oligomer distribution can vary by process, impacting performance and reproducibility—verify by CoA.
Cloud point and viscosity management may require formulation aids (e.g., alcohols, salts).
Thermal/acid stability is lower than for some ether-based nonionics due to the acetal glycosidic bond.
If your application prioritizes maximum biodegradability and renewable content, decyl or lauryl glucosides are strong candidates. If high-temperature/strong-base stability is critical, alternative nonionics (e.g., alkyl polyglucosides with tailored DP or EO/PO block copolymers) may perform better albeit with greener tradeoffs.
Pharmaceutical Uses
No therapeutic claims are made. The following describes potential roles as a manufacturing/formulation excipient (general literature guidance):
Formulation functions:
Nonionic surfactant/solubilizer: enhances wetting and solubilization of poorly water-soluble actives in aqueous or hydroalcoholic vehicles.
Mild cleansing and foaming agent: used in personal-care and topical preparations where reduced irritation is desired compared to anionics.
Stabilizer: can reduce aggregation or precipitation of hydrophobic components in suspensions and emulsions.
Advantages:
Sugar-derived headgroup and absence of ionic charge provide good biocompatibility and reduced interaction with electrolytes.
Readily biodegradable and derived from renewable feedstocks.
Considerations for regulated use:
Excipient grade specifications (microbial limits, residual solvents, assay of active matter, peroxide value, color) must be verified per pharmacopeial or internal standards.
Interaction with actives and packaging should be assessed (sorption, leachables). Nonionic surfactants can influence preservative efficacy—perform preservative effectiveness testing if applicable.
Thermal and pH stability windows should be respected to prevent glycosidic hydrolysis (prefer neutral pH, moderate temperatures during processing).
Item-specific pharmacopeial status, compliance, and excipient grade for this SKU: Not specified for this item; refer to CoA/Spec Sheet. This product is supplied for research use only.
Physical Properties
Item-specific specifications: Not specified for this item; refer to CoA/Spec Sheet.
General/literature characteristics for α-decyl glucoside (nonionic surfactant):
Physical state/appearance (literature): typically a waxy solid or viscous paste at ambient temperature; often supplied commercially in aqueous solution concentrates. Actual appearance for this SKU: Not specified for this item; refer to CoA/Spec Sheet.
Solubility (literature): readily soluble in water; forms clear to opalescent solutions above the critical micelle concentration (CMC). Soluble in polar organics (e.g., ethanol) and dispersible in many formulations containing water and co-solvents.
Critical micelle concentration (literature): typically in the low millimolar range (≈1–3 mM in pure water at ~25 °C), decreasing with added electrolyte or co-solvent.
Krafft point (literature): below or near room temperature for decyl chain length; micelle formation readily occurs at laboratory conditions.
HLB (literature): in the range consistent with mild, water-soluble nonionic surfactants used for solubilization and cleansing; exact HLB value varies by method/vendor.
pKa: not applicable (nonionic; no titratable groups in the working pH range).
Partitioning behavior: amphiphilic; does not have a single logP descriptor due to micellization; exhibits strong surface activity and lowers surface/interfacial tension.
Notes for use:
Aqueous solutions may foam; viscosity depends on concentration, temperature, and ionic strength.
Avoid overheating dry material to prevent degradation of the glycosidic bond (general glycoside behavior).
Quality and Grades
Item-specific grade/purity and stabilizers: Not specified for this item; refer to CoA/Spec Sheet.
Guidance for interpreting grades (general):
Research grade: typically suitable for synthetic, formulation, and biochemical applications where low levels of ionic/metal contaminants are acceptable. UV-transparency and residue on evaporation are not necessarily controlled unless stated.
High-purity or assay-specified surfactant: when provided, indicates defined content of the active alkyl glucoside (w/w%), moisture, and potential residual alcohol/sugar byproducts. For chromatography or assay-sensitive applications, choose lots with tighter impurity and moisture control.
Impurity considerations (general for alkyl glucosides):
Residual alcohol (decanol), oligoglycosides (e.g., di-/tri-glycosides), and moisture are the most common impurities. These can affect CMC, foaming, and solubilization efficacy.
Inorganics (ash) and color bodies are minimized in high-purity material; if color is critical, select lots with low APHA/hazen color when specified.
Documentation:
For assay, moisture (Karl Fischer), residual solvents, and oligomer distribution, consult the item’s CoA/Spec Sheet. When performing quantitative biochemistry, verify lot-to-lot CMC and activity as needed.
If your application requires specific parameters (e.g., low UV absorbance, metal content, or defined oligo-distribution), contact technical support for an appropriate lot selection. All unspecified parameters for this SKU: Not specified for this item; refer to CoA/Spec Sheet.
Reaction and Applications
While primarily used as a nonionic surfactant, α-decyl glucoside can play valuable roles in synthetic and analytical workflows.
Typical applications (literature/general):
Micellar and aqueous-phase organic synthesis: serves as a benign surfactant medium enabling water as solvent for cross-couplings, nucleophilic substitutions, and reductions. Micelles can concentrate hydrophobes and enhance rates.
Solubilization of hydrophobic reagents: improves handling and dosing of poorly soluble substrates, dyes, and catalysts in aqueous or mixed media.
Protein and membrane studies: milder alternative to anionic surfactants for extracting or stabilizing membrane-associated biomolecules (screen concentration to minimize denaturation).
Cleaning/processing steps in labs: effective at removing organic residues from glassware and equipment; rinses well in water.
Mechanistic notes:
Amphiphile self-assembly into micelles (or vesicles at higher concentrations/with salts) creates hydrophobic cores and polar coronas; reagents partition according to polarity.
Reaction acceleration can arise from increased local concentrations within micellar cores and interfacial effects; rate enhancements are substrate- and surfactant-dependent.
Practical guidance:
Start with 1–5 wt% in water for micellar catalysis; adjust salt (e.g., NaCl) to tune micelle size if needed.
Degassing is often unnecessary, but for air-sensitive catalysts, standard inert techniques still apply.
Removal post-reaction: extract with organic solvents; or break micelles with salt/solvent, then separate. Residual surfactant can be removed by aqueous washes or SPE depending on product polarity.
All application specifics should be verified under your conditions; no item-specific validations are provided for this SKU.
Reaction Conditions
The following guidance summarizes common laboratory conditions where α-decyl glucoside functions effectively as a surfactant medium or additive (general literature; optimize per substrate/catalyst):
Micellar catalysis in water:
Concentration: 1–5 wt% surfactant in deionized water is a typical starting range; adjust to maintain clarity and manageable viscosity.
Temperature: ambient to 60 °C commonly used; higher temperatures can reduce viscosity but avoid prolonged heating under acidic conditions.
Salts/co-solvents: 0–200 mM NaCl or 5–20% v/v ethanol/isopropanol may tune micelle size and substrate solubility; co-solvents often lower CMC.
Representative transformations (reported with nonionic glucosides):
Cross-couplings (e.g., Suzuki–Miyaura): Pd-catalyzed reactions in aqueous micelles at 25–50 °C with modest base (e.g., K2CO3); times 1–24 h depending on substrate.
Nucleophilic substitutions: SNAr or allylic substitutions with phase-transfer-like benefits; room temperature to 50 °C.
Reductions/oxidations: transfer hydrogenations and TEMPO oxidations proceeding in micellar media with improved mass transfer.
Workup considerations:
Post-reaction, extract organics with EtOAc/MTBE. Residual surfactant remains mostly in aqueous phase; repeated extractions or salting-out improves separation.
For product sensitive to emulsions, break micelles with brine or alcohol before extraction.
Expected yields: highly substrate-dependent; micellar media often match or improve yields versus organic solvents, but empirical optimization is essential.
Item-specific validated conditions for this SKU: Not specified for this item; refer to CoA/Spec Sheet.
Safety and Handling
Item-specific hazard and GHS data: Not specified for this item; refer to the SDS for authoritative classification, pictograms, signal word, and H/P statements.
General safety profile for nonionic alkyl glucosides (literature/typical):
Toxicological profile: generally considered to have low acute toxicity and to be milder than many anionic surfactants; may cause eye irritation and, at high concentrations or prolonged contact, skin dryness/irritation.
Combustibility: organic surfactants can burn; keep away from ignition sources, especially in dry form or in organic solvent blends.
PPE and handling practices (good laboratory practice):
Wear safety glasses or splash goggles, lab coat, and appropriate chemically resistant gloves (e.g., nitrile). Use in a well-ventilated area or fume hood to minimize aerosol formation when preparing solutions.
Avoid inhalation of dusts/aerosols and prolonged skin contact. Wash thoroughly after handling.
Storage incompatibilities and stability:
Compatible with most buffer salts and many co-solvents (ethanol, isopropanol). Avoid strong oxidizers and strong acids/bases at elevated temperature which can hydrolyze the glycosidic bond.
Surfactants can solubilize other chemicals; clean spills with awareness they may spread. Use absorbents compatible with aqueous systems.
First-aid overview (general):
Eyes: Rinse cautiously with water for several minutes. Remove contact lenses if present and easy to do. Seek medical attention for persistent irritation.
Skin: Wash with soap and water. Remove contaminated clothing. Seek medical advice if irritation persists.
Inhalation: Move to fresh air. Seek attention if symptoms occur.
Ingestion: Rinse mouth. Do not induce vomiting unless directed by medical personnel.
Always consult the product-specific SDS prior to use.
Solvent Selection
This product is a nonionic surfactant rather than a bulk solvent; conventional solvent selection frameworks do not directly apply. However, its performance depends strongly on the aqueous/organic medium.
General solvent compatibility and selection (literature/guidance):
Water: readily soluble; forms micelles above the CMC, enabling solubilization of hydrophobic substrates and membrane proteins.
Alcohols (ethanol, isopropanol): miscible; co-solvents can lower CMC and modify cloud point and viscosity.
Polar aprotics (DMSO, DMF): typically compatible at low percentages in water; high levels may disrupt micellization—evaluate empirically.
Salts/buffers: ionic strength and pH can modulate micelle size and stability; neutral to mildly buffered conditions are generally preferred to preserve the glycosidic linkage.
When to choose decyl vs related alkyl glucosides:
Octyl glucoside: higher CMC, milder solubilization; favored for labile protein work where easy removal by dilution/dialysis is desired.
Decyl glucoside: intermediate hydrophobicity; stronger solubilization than C8 and better foaming/cleansing profiles—balanced for general biochemical and formulation needs.
Lauryl (dodecyl) glucoside: lower CMC and stronger solubilization; may be harder to remove and can increase viscosity.
Practical tips:
Prepare stock solutions in water or aqueous alcohol; avoid strong acid/base and high temperatures which can promote hydrolysis.
For spectroscopy, check background absorbance at target wavelengths; choose high-purity/low-color lots when UV work is critical.
Additional storage guidance (general best practice for alkyl glucosides):
Keep container tightly closed to minimize moisture uptake and contamination. If supplied as an aqueous solution, protect from microbial growth; consider sterile technique or preservatives for long-term storage.
Avoid prolonged exposure to elevated temperature and strong acids/bases which can cleave the glycosidic bond. Store away from strong oxidizers.
If material solidifies or becomes highly viscous at cooler temperatures, gently warm (e.g., 30–40 °C) and mix to homogenize before use.
Reconstitution/preparation (general):
To prepare working solutions, add the weighed amount to water or buffer with stirring. Mild warming can aid dissolution. Adjust ionic strength and co-solvent content as needed for your application.
Filter sterilization (0.22 µm) can be used for biological applications when compatible with viscosity and concentration.
Shelf life and stability specifics for this SKU (assay, moisture, microbial limits): Not specified for this item; refer to CoA/Spec Sheet.
Research Use Only: This material is intended for laboratory research use. No medical or clinical use is intended or implied.
Structure and Identity
Decyl glucoside, alpha- is a nonionic alkyl glucoside surfactant formed by glycosidic linkage of a decyl (C10) chain to the anomeric carbon of glucose in the α-configuration.
SKU: D1024027
Product name: Decyl glucoside, alpha-
CAS: 29781-81-5
Category: Small molecules and compound library (nonionic surfactant)
InChIKey (item-specific): Not specified for this item; refer to CoA/Spec Sheet. (A placeholder “157656” was provided but is not a standard InChIKey.)
SMILES (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
Structural features (general/literature description):
Core scaffold: a pyranose (glucopyranose) ring bearing hydroxyls at C2, C3, C4, and C6.
Glycosidic bond: α-O-glycosidic linkage at C1 (anomeric carbon) to an n-decyl chain (–O–(CH2)9CH3).
Functional groups: multiple secondary alcohols, one primary alcohol, one acetal (glycosidic) ether, and a linear aliphatic chain.
Stereochemistry: glucose ring typically as α-D-glucopyranoside (defined stereocenters at C1–C5 of glucose); α-anomer implies axial anomeric substituent in the chair conformation.
Molecular identifiers (literature/computed, typical for α-D-decyl glucoside):
Molecular formula (literature): C16H32O6
Molecular weight (literature): ~320.43 g/mol
2D structure in words: a six-membered chair glucose ring with four equatorial hydroxyls (C2–C4, C6 sidechain), and an axial anomeric oxygen at C1 connecting to a straight C10 alkyl chain. The molecule is amphiphilic with a hydrophilic sugar headgroup and a hydrophobic decyl tail.
Synthetic Utility
Beyond its role as a surfactant medium, α-decyl glucoside has structural features that can be leveraged in synthesis and materials:
Functional group landscape:
Multiple free hydroxyl groups (primary at C6, secondary at C2–C4) enable selective derivatization (esterification, etherification, silylation) to generate amphiphiles with tailored HLB or to prepare sugar-based ligands.
The anomeric position is blocked by the decyl glycoside, conferring acetal stability under neutral conditions but susceptibility to acid catalysis.
Utility in synthesis and materials (literature):
Micellar catalysis: facilitates aqueous-phase cross-coupling, nucleophilic substitution, and radical reactions with reduced organic solvent usage.
Template/structure-directing agent: guides formation of mesoporous inorganic/organic materials via self-assembly.
Protecting-group scaffold: sugar hydroxyls can serve as temporary handles for regioselective functionalization, followed by mild deacylation.
Ligand design: derivatization of hydroxyls can afford glycoamphiphiles for biomimetic interfaces or phase-transfer auxiliaries.
Practical notes:
Selective acylation/alkylation often exploits differential reactivity (primary > secondary). Use protecting-group strategies for regioselectivity.
Avoid strong acids for extended periods to prevent cleavage of the decyl glycosidic bond; neutral or basic conditions are preferred for downstream modifications of the sugar ring.
Item-specific reactivity specifications, residual moisture, or stabilizers: Not specified for this item; refer to CoA/Spec Sheet.
Target Specificity
Not applicable. This product is a small-molecule nonionic surfactant and is not an antibody, probe, or biologic. No antigen/epitope, clone, isotype, or species reactivity information applies.
Any target-binding or biological specificity data for this SKU: Not specified for this item; refer to CoA/Spec Sheet.
Domande frequenti
What is the purity of this product?
This product is supplied at ≥97% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.
How should this product be stored?
Store at room temperature.
What are the CAS number, molecular formula and molecular weight?
The CAS Number is 29781-81-5. InChIKey JDRSMPFHFNXQRB-LJIZCISZSA-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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