Acetyl-β-cyclodextrin

Cat. No.: A121142

Storage

Store at 2-8°C

Shipped In

Wet ice

Vue d’ensemble

Cyclodextrins (CD) are cyclic oligosaccharides composed of D-glucose units connected via α(1,4) glycosidic bonds. Common cyclodextrins contain six (α-CD); seven (β-CD) or eight (gamma-CD) D-glucose units. Cyclodextrins are sometimes derivitized through esterification at positions two, three and/or six. Acetyl-β-cyclodextrin is used in the development of recognition and separation technologies to resolve enantiomers based on chiral properties and size. Acetyl-β-cyclodextrin is used in chiral selection and separation by capillary electrophoresis and liquid chromatography.

Specifications

Conditions de stockage de stockage

Store at 2-8°C

Expédié en

Wet ice

Ce produit nécessite l'expédition en chaîne froide. Les services terrestres et autres services économiques ne sont pas disponibles.

Application Protocols

No vendor-validated protocols are provided for this SKU. The following are general, literature-based starting points; adjust to your system and consult the CoA/SDS.

• Preparation of an inclusion complex in organic solvent (general):

  • Dissolve acetyl-β-CD (e.g., 50–200 mM) and guest (0.5–1.5 equiv) in dry CHCl3 or acetone. Stir 2–16 h at room temperature. Monitor by 1H NMR for diagnostic cavity-induced shifts. Isolate by slow evaporation or anti-solvent addition (hexanes/diethyl ether). Dry under vacuum.

• NMR sample preparation:

  • Weigh ~5–15 mg into an NMR tube, add 0.6 mL CDCl3 or acetone-d6, sonicate gently if needed. Acquire 1H/13C; for DS profiling, use HSQC/HMBC and integrate acetate methyl signals.

• Thin-film/coating casting (general):

  • Prepare a 1–10% w/v solution in acetone or EtOAc. Filter (0.45 μm PTFE). Cast on substrate; allow to evaporate under a fume hood. Post-dry under vacuum (25–40°C) to constant mass.

• Chiral selector in CE (non-aqueous CE, literature):

  • Prepare a background electrolyte in a polar organic solvent (e.g., MeOH/ACN) and add acetyl-β-CD at 5–20 mM. Optimize voltage and temperature for resolution of target enantiomers.

Item-specific recommended concentrations, solvent choices, and validated applications: Not specified for this item; refer to CoA/Spec Sheet.

Biological Roles

This product is intended for research use only. No medical or clinical claims are made.

• General/cyclodextrin background (literature):

  • Cyclodextrins (CDs) are cyclic oligosaccharides that form inclusion complexes with diverse small molecules. Native β-CD and certain hydrophilic derivatives (e.g., HPβCD) are widely used in biochemical research to modulate solubility and to probe host–guest interactions in aqueous systems.
  • Acetylation markedly reduces aqueous solubility and hydrogen-bonding capacity, shifting the preferred operating environment to organic solvents. As such, acetyl-β-CD is less commonly used directly in biological media but can be employed to pre-form inclusion complexes or for studies of recognition in low-water environments relevant to membranes and hydrophobic phases.

• Research contexts:

  • Model systems for hydrophobic binding: Investigations of non-covalent inclusion in solvents of low polarity, providing insights into dispersion- and shape-driven recognition with limited hydrogen bonding.
  • Materials interfacing with bioanalytes: Organophilic coatings incorporating acetyl-β-CD can capture volatile or hydrophobic bio-relevant molecules (e.g., steroids, terpenoids) prior to analytical detection (GC/LC), outside of living systems.

• Notes and limitations:

  • If aqueous or cell-based studies are required, hydrophilic CDs (β-CD, HPβCD, SBE-β-CD) are typically preferred. Any biological testing should be conducted under appropriate institutional approvals and safety frameworks.

Buffer Applications

Acetyl-β-cyclodextrin is not typically employed as a buffering agent due to the absence of suitable acid–base functionality and its limited water solubility.

• Practical guidance:

  • For aqueous buffers requiring cyclodextrin-mediated inclusion of hydrophobic analytes, consider native β-CD or hydroxypropyl-β-CD, which dissolve readily in common biological and chromatographic buffers (e.g., phosphate, Tris, acetate) and do not significantly alter buffer capacity at typical concentrations (literature).
  • If acetyl-β-CD is used in non-aqueous analytical methods (e.g., as an additive in organic mobile phases), its role is as a chiral selector or host, not as a pH buffer. Ensure complete dissolution in the chosen organic solvent and confirm compatibility with instrument materials.

• Item-specific buffer compatibility: Not specified for this item; refer to CoA/Spec Sheet.

In summary, select a conventional buffering system appropriate to your application and use cyclodextrins (including acetylated forms) solely as supramolecular additives where justified.

Green Alternatives

Selection of a cyclodextrin derivative impacts solvent demands and waste. Consider greener choices when aqueous processing is feasible.

• Greener substitutions (general/literature):

  • Native β-cyclodextrin (β-CD): Water-soluble; enables aqueous host–guest chemistry, reducing halogenated solvent use. Tradeoff: poor solubility for hydrophobic guests; weaker interactions in nonpolar matrices.
  • Hydroxypropyl-β-CD (HPβCD): High water solubility and established safety profile as an excipient; excellent for solubilizing hydrophobic molecules in water. Tradeoff: broader DS distribution and higher viscosity.
  • Sulfobutylether-β-CD (SBE-β-CD): Anionic, water-soluble; strong binding to cationic guests in aqueous media. Tradeoff: ionic nature may be incompatible with certain organic-phase processes.

• When Acetyl-β-CD is advantageous:

  • Non-aqueous systems demanding organosolubility, low water activity, or compatibility with hydrophobic polymers.

• Process considerations:

  • If you must use Acetyl-β-CD, prefer greener organic solvents (e.g., EtOAc, 2-MeTHF) over chlorinated solvents when performance allows. Employ solvent recycling and low-temperature evaporation to minimize energy.

• Summary table (general comparison):

  • Acetyl-β-CD: organosoluble; supports non-aqueous inclusion and CSP fabrication; reduced water use but may require halogenated solvents.
  • β-CD/HPβCD/SBE-β-CD: aqueous processing; reduced VOC emissions; may not function in hydrophobic matrices.

Note: These are literature-based considerations. Verify performance for your specific system and consult the CoA for this SKU before substitution.

Pharmaceutical Uses

For research use only. No medical or clinical use is intended or implied for this product.

• General context (literature):

  • Cyclodextrins are used in pharmaceutical development primarily as excipients to enhance solubility and stability of actives. Hydrophilic derivatives such as hydroxypropyl-β-CD (HPβCD) and sulfobutylether-β-CD (SBE-β-CD) have pharmacopeial recognition and established safety profiles for certain applications.
  • Acetyl-β-cyclodextrin, being organophilic and poorly water-soluble, is not commonly employed as an aqueous solubilizer. Its typical roles are in non-aqueous processing, pre-formulation studies of host–guest interactions, or as a precursor to other functionalized CDs.

• Development considerations:

  • If exploring cyclodextrin-based delivery in water, screen HPβCD or SBE-β-CD instead of acetyl-β-CD.
  • For solid dispersions or coatings processed from organic solvents, acetyl-β-CD may serve as a matrix component or affinity modifier; verify residual solvent limits and DS reproducibility.

• Compendial status:

  • No pharmacopeial status is claimed for this SKU. For any regulated work, obtain and review the CoA and SDS, and confirm compliance requirements.

• Item-specific excipient specifications (microbial limits, residual solvents, endotoxin): Not specified for this item; refer to CoA/Spec Sheet.

Physical Properties

• Item-specific physical data:

  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
  • Melting point: Not specified for this item; refer to CoA/Spec Sheet.
  • Solubility: Not specified for this item; refer to CoA/Spec Sheet.
  • Density, refractive index, pKa/logP, UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.

• General/literature characteristics (for context; verify against CoA for this SKU):

  • Form: Typically an amorphous or microcrystalline solid (literature).
  • Solubility profile: Acetylation suppresses hydrogen bonding, decreasing water solubility and increasing solubility in organic solvents such as dichloromethane, chloroform, acetone, ethyl acetate, DMF, and DMSO (literature). Water miscibility is markedly reduced versus native β-CD.
  • Thermal behavior: Peracetylated β-CD variants often show broad melting/decomposition ranges rather than a sharp melting point due to macrocyclic and polymer-like packing (literature). Avoid prolonged heating to prevent acetate migration or hydrolysis in moist conditions.
  • Hygroscopicity: Less hygroscopic than native β-CD, but prolonged exposure to moisture can lead to slow ester hydrolysis (literature).

• Practical notes:

  • For analytical confirmation of DS and purity, 1H/13C NMR in CDCl3, DMSO-d6, or acetone-d6 is commonly employed (literature).
  • Solubility and viscosity can vary with DS; pilot dissolution trials in a dry organic solvent are recommended if item-specific solubility is not available.

Quality and Grades

• Item-specific quality information:

  • Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.

• Interpretation and guidance:

  • In the absence of an explicit grade, consult the CoA for assay method (e.g., NMR integration, HPLC/ELSD), degree of substitution (DS), and residual solvent/moisture levels relevant to your application.
  • For chromatography or supramolecular applications, key quality attributes typically include: accurate DS distribution, low inorganic residue, and absence of low-mass saccharide byproducts.
  • For materials science or host–guest studies, batch-to-batch reproducibility of DS and cavity accessibility drive performance; verify via NMR and elemental analysis.

• Common grade descriptors (general context; not item-specific):

  • “Research grade”/“Laboratory grade”: suitable for general R&D; may not include low-UV or trace-metal specifications.
  • “HPLC grade” (for solvents) or “low-UV” descriptors are not applicable here unless specified.

• Stabilizers/additives: None indicated in Product Data. If stabilizers are used in a specific lot, they will be listed on the CoA/SDS.

• Documentation checklist before use:

  • Obtain CoA and SDS for this SKU to confirm DS, purity, residual solvents, moisture, and recommended analytical acceptance criteria aligned with your protocol.

Reaction and Applications

Acetyl-β-cyclodextrin is widely used as an organophilic cyclodextrin derivative for supramolecular chemistry, separations, and materials.

• Representative applications (literature, general):

  • Chiral recognition and separations: Basis for chiral stationary phases (CSPs) and chiral selectors in GC/CE; acetylation tunes cavity polarity and rim interactions to enhance enantioselectivity for nonpolar analytes.
  • Host–guest chemistry in organic media: Inclusion complexes with aromatic, aliphatic, and heteroaromatic guests to modulate reactivity, solubility, and crystallization behavior outside aqueous environments.
  • Materials and coatings: Film formation and blending with polymers to control permeability, release profiles, or capture of volatile organic compounds.
  • Intermediate in synthesis: Protecting-group platform for regioselective transformations of β-CD; acetate masks OH groups to direct subsequent functionalization (e.g., selective deprotection or substitution at C6).

• Practical laboratory tips:

  • Maintain dry conditions to prevent partial hydrolysis; store and handle under low humidity.
  • For inclusion complex preparation, dissolve host and guest in a mutual organic solvent (e.g., CHCl3, DCM, acetone), then induce co-precipitation or solvent evaporation; characterize by 1H NMR (shift/NOE), MS, and PXRD.
  • When used as a chiral selector in solution, optimize solvent polarity and temperature to balance complex stability with analyte mobility.

• Cross-reference: If employing as a precursor for tailored derivatives (e.g., per-6-substituted β-CD), consider stepwise deacetylation (Zemplén conditions) to unmask targeted positions (literature).

Reaction Conditions

The following are general, literature-based conditions relevant to preparing, modifying, or using acetyl-β-cyclodextrin. They are not item-specific specifications.

• Deacetylation (Zemplén methanolysis):

  • Conditions: Catalytic NaOMe (≈0.05–0.2 equiv per acetate) in dry MeOH at 0–25°C.
  • Notes: Primary acetate at C6 often cleaves faster than secondary acetates; quench with acetic acid and remove salts. Monitor by TLC/NMR.

• Selective functionalization at C6:

  • Tosylation: Limited deacetylation at C6 followed by TsCl/py or TsCl/DMAP in pyridine/CH2Cl2 (0–25°C) affords 6-OTs sites for nucleophilic substitution.
  • Nucleophilic substitutions: Azide, thio, or ether installations under SN2 conditions in polar aprotic solvents (DMF/DMSO), 25–80°C, depending on nucleophile.

• Inclusion complex formation in organic media:

  • Dissolve host and guest in CHCl3, DCM, acetone, or EtOAc; stir 1–24 h at ambient temperature. Isolate by slow evaporation or anti-solvent addition (e.g., hexanes) to induce co-precipitation. Characterize by NMR/NOESY and PXRD.

• CSP fabrication (general):

  • Immobilization: React acetyl-β-CD with activated silica or polymer linkers (e.g., isocyanate or epoxide-functional supports) in anhydrous solvents (toluene, THF) at 50–90°C; cure and condition prior to chromatographic use.

• Stability considerations:

  • Avoid strong base/acid and aqueous conditions that promote hydrolysis or transesterification. Work under dry nitrogen/argon where feasible.

Note: Optimize equivalents, temperatures, and times for your substrate and DS; consult primary literature for scale-up.

Safety and Handling

• Item-specific hazard data from Product Data:

  • Signal Word: Not specified for this item; refer to SDS.
  • H-Statements: Not specified for this item; refer to SDS.
  • GHS Classification: Not specified for this item; refer to SDS.
  • Pictograms: Not specified for this item; refer to SDS.

• General safety guidance (consult SDS for authoritative instructions):

  • Expected hazards (literature): Low volatility solid; may cause irritation to eyes, skin, and respiratory tract as a fine powder. Dust may present mechanical irritation and can form combustible dust-air mixtures—minimize dust generation and ignition sources.
  • Personal protective equipment: Lab coat, safety glasses, and chemically resistant gloves (e.g., nitrile). Use a dust mask/respirator if handling large quantities of powder or if airborne particulates are generated; work in a fume hood for weighing and transfers.
  • Handling practices: Keep containers tightly closed. Avoid moisture ingress—esters can hydrolyze slowly in the presence of water and base. Use dedicated, dry utensils; purge containers with dry inert gas if frequent access is expected.
  • Incompatibilities (literature): Strong bases and nucleophiles (risk of deacetylation/transesterification), strong acids (hydrolysis), strong oxidizers. Avoid prolonged contact with aqueous media unless hydrolysis is intended.
  • First-aid overview: In case of eye/skin contact, rinse with water for several minutes; remove contaminated clothing. If inhaled, move to fresh air. If ingested, rinse mouth and seek medical attention. Always follow the SDS for emergency procedures.
  • Fire-fighting: Use water spray, CO2, or dry chemical; combustion may produce CO/CO2 and acetic acid vapors (literature).

Solvent Selection

Acetylation converts native β-CD from a highly hydrophilic macrocycle to a more organophilic host. Solvent choice substantially affects dissolution, viscosity, and host–guest behavior.

• Polarity and miscibility (literature, general):

  • Good solvents: dichloromethane (DCM), chloroform, acetone, ethyl acetate, tetrahydrofuran (THF), dimethylformamide (DMF), dimethyl sulfoxide (DMSO).
  • Limited/poor solubility: water and aqueous buffers; methanol/ethanol may be moderate depending on DS.
  • Dry, aprotic media often give the best solubility and stability of acetate esters.

• Practical selection tips:

  • For NMR characterization: CDCl3 or acetone-d6 commonly yield well-resolved spectra for peracetylated derivatives; DMSO-d6 if higher DS heterogeneity requires better solvation.
  • For host–guest assembly in organic phase: DCM, EtOAc, or CHCl3 balance volatility and solvation; add a non-polar cosolvent (hexanes) to modulate inclusion complex precipitation if needed.
  • For processing and film formation: Acetone and EtOAc favor faster drying; DMF/DMSO enable higher loading but slow evaporation.

• Comparison (general):

  • Native β-CD: water-soluble; poor solubility in organics; ideal for aqueous inclusion complexes.
  • Acetyl-β-CD: organosoluble; tailored for non-aqueous inclusion chemistry, coatings, and chiral selectors where water is undesirable.

• Item-specific solubility data: Not specified for this item; refer to CoA/Spec Sheet. Conduct a small-scale solvent screen if your method is sensitive to DS or viscosity.

Storage and Reconstitution

• Storage (from Product Data):

  • Store at 2–8°C.
  • Shipped on wet ice.

• General handling and stability (literature guidance):

  • Keep container tightly closed in a dry place. Protect from moisture to minimize ester hydrolysis; consider desiccant and/or inert-gas backfill if frequently opened.
  • Allow container to equilibrate to room temperature before opening to avoid condensation.

• Reconstitution and dissolution:

  • Item-specific solubility is not provided. In general (literature), acetyl-β-cyclodextrin dissolves in dry organic solvents such as dichloromethane, chloroform, acetone, ethyl acetate, DMF, and DMSO. Start with small volumes and gentle warming (≤40°C) if needed; avoid prolonged heating.
  • For aqueous systems, prepare organic stock solutions and, if required, add to formulations containing compatible cosolvents; expect limited water miscibility.

• Aliquoting and shelf life:

  • If preparing stock solutions, store in amber, airtight vials at 2–8°C for short terms; for longer-term storage, freeze at −20°C in dry, aprotic solvent if compatible. Avoid repeated freeze–thaw cycles; dispense single-use aliquots.

• Documentation:

  • Refer to the CoA/Spec Sheet for lot-specific stability, moisture limits, and any additional storage precautions. Always consult the SDS for safety-critical instructions.

Research use only.

Structure and Identity

Brief overview: Acetyl-β-cyclodextrin is an acetylated derivative of β-cyclodextrin (β-CD), in which some or all of the secondary (C2/C3) and primary (C6) hydroxyl groups on the seven glucopyranose units are converted to acetate esters, increasing hydrophobicity and organic-solvent compatibility.

• Item-specific identifiers from Product Data:

  • CAS: Not specified for this item; refer to CoA/Spec Sheet.
  • 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 (general/literature description):

  • Core scaffold: β-cyclodextrin is a cyclic heptamer of α-1→4-linked D-glucopyranose units, forming a torus (truncated cone) with a hydrophobic inner cavity and hydrophilic rims in the native form.
  • Functional groups: Multiple acetate esters (–O–C(O)CH3) replacing native hydroxyls; remaining free OH, if any, depend on degree of substitution (DS).
  • Stereochemistry: Each glucose is D-configuration; all anomeric linkages are α; numerous fixed stereocenters across the ring render the macrocycle highly stereodefined.
  • Variants (literature): “Peracetylated” β-CD (heptakis(2,3,6-tri-O-acetyl)-β-CD) bears 21 acetates; partially acetylated materials possess lower DS. Exact DS and site distribution are item-specific and should be confirmed by CoA/NMR.

• 2D structural description (general): Seven chair-conformation glucopyranose units linked head-to-tail in a ring; secondary rim (C2/C3) and primary rim (C6) oxygen atoms bearing acetyl substituents to varying extents, narrowing the cavity entrance and masking hydrogen-bond donors.

Synthetic Utility

Acetyl-β-cyclodextrin is a versatile intermediate and functional material in carbohydrate chemistry and supramolecular synthesis.

• Protecting-group platform (literature):

  • Global acetylation masks the 2-, 3-, and 6-OH groups, enabling regioselective manipulations. Selective deprotection (e.g., Zemplén methanolysis) can unmask primary 6-OH positions preferentially, allowing further substitution (tosylation, azidation, etherification) while maintaining protection elsewhere.
  • Stepwise strategies exploit differential reactivity of primary vs secondary esters to install substituents at the rim(s), generating amphiphilic or functionalized β-CDs (e.g., per-6-alkyl, per-6-thio, or bridged derivatives).

• Building block for chiral selectors and materials:

  • Covalent attachment of acetyl-β-CD to silica or polymer backbones creates chiral stationary phases for HPLC/GC; acetyl groups modulate inclusion strength and steric environment for enantiodiscrimination.
  • Blending into polymer matrices or forming crosslinked networks yields organophilic host surfaces for VOC capture or controlled release in non-aqueous contexts.

• Host-mediated chemistry:

  • Inclusion of reactive guests in organic solvents can alter local concentration and orientation, influencing reaction outcomes (e.g., photodimerizations or radical processes) in a confined hydrophobic cavity (literature).

• Analytical handles:

  • 1H/13C NMR in CDCl3/acetone-d6 guides DS assessment; IR shows strong ester C=O bands (~1735 cm−1), and MS (MALDI-TOF) reveals DS distribution. These are valuable for batch qualification prior to downstream synthesis.

Target Specificity

Not applicable. This product is a small-molecule macrocyclic reagent (acetylated β-cyclodextrin) and not a biological targeting reagent or antibody. No antigen, epitope, species reactivity, clone, or isotype information applies.