Ethyl 3-cyclohexylbutanoate - ≥95% , CAS No.28811-80-5

CAS: 28811-80-5 Cat. No.: E978364 Formula: C₁₂H₂₂O₂ Peso molecolare: 198.300 Numero EC: 103-867-4

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

Specifiche e purezza

≥95%

Condizioni di conservazione di stoccaggio

Room temperature

Purezza

≥95%

Nomi e identificatori

• Sorrisi canonici: CCOC(=O)CC(C)C1CCCCC1
• IUPAC Name: ethyl 3-cyclohexylbutanoate
• InChIKey: ILIIDBKOIBLECO-UHFFFAOYSA-N
• INCHI: 1S/C12H22O2/c1-3-14-12(13)9-10(2)11-7-5-4-6-8-11/h10-11H,3-9H2,1-2H3
• Peso molecolare: 198.300

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Classe Fatty Acyls
      • Subclass Fatty acid esters

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Classe: Fatty Acyls
• Subclass: Fatty acid esters
• Intermediate Tree Nodes: Not available
• Direct Parent: Fatty acid esters
• Alternative Parents: Carboxylic acid esters Monocarboxylic acids and derivatives Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic homomonocyclic compounds
• Substituents: Fatty acid ester - Carboxylic acid ester - Monocarboxylic acid or derivatives - Carboxylic acid derivative - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - Aliphatic homomonocyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.
• External Descriptors: Not available

Data sources

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.

DOI: 10.1186/s13321-016-0174-y

Proprietà chimiche e fisiche

• Peso molecolare: 198.300 g/mol
• XLogP3: 3.900
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 198.162 Da
• Monoisotopic Mass: 198.162 Da
• Topological Polar Surface Area: 26.300 Ų
• Heavy Atom Count: 14
• Formal Charge: 0
• Complexity: 171.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 1
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Application Protocols

No tested biological assay protocols or analytical application parameters are provided for this SKU. Typical laboratory uses derive from standard organic synthesis workflows:

• Example workflows (general):
  • Hydrolysis to the acid followed by amide coupling (EDC/HOBt or HATU) to prepare 3-cyclohexylbutanamides.
  • Lipase screening: incubate with immobilized CAL-B in heptane or 2-MeTHF with an alcohol nucleophile; monitor conversion by GC.
  • GC method development: nonpolar column (e.g., 5% phenyl–95% dimethylpolysiloxane), oven 60→280 °C, detect ester and acid/alcohol products.

Refer to your institutional SOPs and method development guidelines for detailed, validated procedures.

Biological Roles

This compound is a synthetic, saturated ethyl ester with a cyclohexyl substituent and has no established endogenous biological role.

• General notes (literature):

  • Aliphatic ethyl esters can be substrates for nonspecific esterases, undergoing hydrolysis to the corresponding carboxylic acid and ethanol. The rate depends strongly on steric and electronic factors; secondary-alkyl esters like this one are typically hydrolyzed more slowly than simple linear esters.
  • Due to its hydrophobicity, the compound would be expected to partition into lipid phases or membranes in model systems; this can be relevant in in vitro assays of esterase activity or permeability modeling.

• Research-only statement: As per Product Data, this material is for research use only. No clinical, diagnostic, or therapeutic use is intended or implied.

Buffer Applications

Not typically applicable. Ethyl 3-cyclohexylbutanoate is a neutral, hydrophobic ester and does not serve as a buffering agent. For aqueous work, select appropriate buffer systems (e.g., phosphate, Tris, HEPES) as required and use this compound only as a substrate or analyte in biphasic or cosolvent systems.

Green Alternatives

When choosing a reagent or solvent system, consider greener options and process-intensification strategies.

• If used as a solvent/diluent:

  • Prefer bio-derived, higher-boiling ethers/esters such as 2-MeTHF or ethyl acetate for comparable solvency but improved sustainability and better life-cycle metrics. Note: Ethyl 3-cyclohexylbutanoate is primarily a substrate, not a common solvent.

• If used as a substrate requiring hydrolysis or transesterification:

  • Employ biocatalysis (lipases in aqueous-organic or solvent-free systems) to replace strong acids/bases and lower E-factors.
  • Use ethanol (formed in situ) capture or reactive distillation to drive equilibrium instead of stoichiometric dehydrating agents.

• If reduction is required:

  • Replace LiAlH4 with catalytic hydrogenation (e.g., Ru/C + H2) or transfer hydrogenation when compatible, to reduce hazardous waste. DIBAL-H may offer a balance for selectivity but still requires careful quench.

• Comparison snapshot (general, literature):

  • 2-MeTHF: renewable, lower peroxide risk vs THF, good for organometallics; water-partition manageable.
  • Ethyl acetate: biodegradable, low toxicity, easy recovery; higher polarity may alter selectivity.
  • Supercritical CO2: green medium for lipase-catalyzed transformations; requires equipment.

Trade-offs: Greener solvents may change solubility and reaction rates; validate with small-scale DoE. Avoid chlorinated solvents where possible, and consider solvent-free or concentrated conditions for enzyme-mediated steps.

Pharmaceutical Uses

No pharmacopeial or excipient status is provided for this item. For research use only.

• General context (literature):
  • Aliphatic esters may appear as flavor/fragrance components or as hydrophobic pro-moieties in medicinal chemistry exploration, but such uses require rigorous safety and regulatory evaluation not covered here.
  • In formulation research, neutral esters can serve as lipophilic vehicles or co-solvents in preformulation studies; compatibility testing with surfactants and oils is necessary.

Any pharmaceutical application would require dedicated qualification, impurity profiling, and compliance with relevant compendia—none of which are specified for this SKU.

Physical Properties

Item-specific specifications are not provided in the Product Data and should be verified on the CoA/SDS.

• Item-specific values:

  • 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/computed expectations for this structure (for research planning only):

  • Physical state: typically a colorless to pale liquid for comparable C12 aliphatic ethyl esters (literature).
  • Boiling point: higher than simple ethyl butyrate due to increased molecular weight and ring; expect in the mid-to-high 200 °C range at 1 atm (literature trend; verify experimentally).
  • Melting point: likely below room temperature (literature trend for similar esters).
  • Density: expected around 0.86–0.92 g/mL at 20–25 °C for C12 aliphatic esters (literature range; verify before critical use).
  • Refractive index: typically 1.42–1.46 (20 °C) for related saturated esters (literature range).
  • Solubility: low in water (insoluble to sparingly soluble); miscible with nonpolar and moderately polar organic solvents (hexanes, toluene, Et2O, CH2Cl2, EtOAc) (literature).
  • LogP: expected >3 due to aliphatic ring and C12 framework (literature estimation).

Note: Use these as qualitative guides only. For regulated or quantitative work, obtain exact values from the certificate of analysis or measure under your conditions.

Quality and Grades

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

• Interpreting grade (general guidance):

  • For synthetic applications, typical grades include technical, laboratory, or ≥95–98% assay. Higher grades (e.g., GC/HPLC grade) control volatile impurities and UV absorbance for analytical use.
  • If a stabilizer or inhibitor is present, it will be listed on the CoA; such additives can influence reactivity in base- or acid-catalyzed transformations. No stabilizer is specified for this item in the Product Data.

• Recommended quality controls for this compound class (best practice):

  • Identity confirmation by 1H/13C NMR (look for ethyl ester quartet/triplet, methine adjacent to cyclohexyl, and ring methylenes), IR (strong C=O ~1735–1750 cm⁻¹), and GC–MS or LC–MS.
  • Purity assessment by GC or HPLC with appropriate detection; headspace GC can quantify residual solvents.
  • Water and acid value: Not specified for this item; measure as needed for moisture-sensitive chemistry.

• Batch documentation: For regulated research, retain CoA lot records and, where applicable, request impurity profiles or residual solvent data.

Reaction and Applications

Ethyl 3-cyclohexylbutanoate serves as a saturated, secondary-alkyl ethyl ester useful in synthesis and in studies requiring a hydrophobic ester scaffold.

• Transformation families (literature/general):

  • Hydrolysis/transesterification: Base- or acid-catalyzed cleavage to 3-cyclohexylbutanoic acid or exchange to alternative alcohol esters (e.g., Me, iPr) using catalytic acid, BF3·Et2O, or enzyme-catalyzed systems (lipases) under mild conditions.
  • Reduction to alcohol: LiAlH4 or DIBAL-H converts the ester to 3-cyclohexyl-1-butanol (via the corresponding primary alcohol); catalytic hydrogenation of the ester is more demanding (e.g., Ru- or Co-based catalysts).
  • Conversion to amide: Aminolysis with amines under activation (e.g., via mixed anhydride or using coupling reagents after hydrolysis to the acid followed by EDC/HATU/DPPA coupling).
  • α-Functionalization: Enolate chemistry at the α-methylene (adjacent to the carbonyl) permits alkylation or acylation using LDA or NaHMDS at low temperature, though the β-sec-alkyl substituent imposes steric hindrance.
  • Hydrogenolysis/hydrogenation: Ring is already saturated; the ester group can be hydrogenolyzed under vigorous conditions; typically stable under mild hydrogenation used for other functional groups.

• Practical tips:

  • For base-catalyzed hydrolysis, employ methanolic KOH or aqueous NaOH (0.5–2 M), monitoring by GC.
  • For selective transesterification, remove the formed ethanol continuously (Dean–Stark or vacuum) to drive equilibrium.
  • Use phase-transfer catalysis to accelerate saponification in biphasic systems due to low water solubility.

Applications: a hydrophobic handle in modifying surface energy of small molecules, probes for esterase activity, or as a model substrate in lipase selectivity screens (literature use-cases).

Reaction Conditions

General literature guidance for common transformations of aliphatic ethyl esters resembling Ethyl 3-cyclohexylbutanoate. Optimize for your system.

• Hydrolysis (saponification):

  • Conditions: 1–2 M NaOH or KOH in EtOH/H2O (1:1 to 4:1), 20–60 °C.
  • Time: 1–6 h depending on sterics; monitor by GC/LC.
  • Workup: Neutralize to pH ~2 with HCl; extract into organic solvent; dry and concentrate.

• Acid-catalyzed transesterification:

  • Catalyst: p-TsOH (0.5–5 mol%) or H2SO4 (0.5–2 wt%).
  • Alcohol: 5–10 equiv; remove EtOH by azeotrope or vacuum to drive equilibrium.
  • Temperature: reflux of chosen alcohol (65–120 °C).

• Enzymatic resolution/transesterification (lipase):

  • Catalyst: CAL-B (immobilized), 5–20 wt%.
  • Solvent: heptane, MTBE, or solvent-free; 25–60 °C.
  • Note: Potential to resolve the β-stereocenter by kinetic resolution with secondary alcohol counterparts.

• Reduction to alcohol:

  • Reagent: DIBAL-H (1.1–2.0 equiv) in toluene or CH2Cl2 at −78 to 0 °C for aldehyde stage; LiAlH4 in Et2O/THF at 0–25 °C for full reduction to primary alcohol.

• Enolate alkylation:

  • Base: LDA or NaHMDS (1.1–1.5 equiv) in THF at −78 to −20 °C; electrophiles: MeI, benzyl bromide, acyl chlorides (for Claisen-type).

These are representative ranges from literature for analogous substrates; actual rates and selectivity will reflect the added steric bulk of the cyclohexyl group.

Safety and Handling

• Item-specific hazard information (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 considerations for aliphatic ethyl esters (literature/good practice):

  • Likely to be combustible; avoid ignition sources and use in a well-ventilated fume hood.
  • May cause mild skin/eye irritation; wear appropriate PPE: lab coat, safety glasses or splash goggles, and nitrile gloves.
  • Inhalation of vapors/mist should be minimized; employ local exhaust ventilation.
  • Avoid contact with strong oxidizers and strong bases/acids that can promote hydrolysis or transesterification.

• First-aid overview (defer to SDS for authoritative instructions):

  • Skin: Wash with soap and water; remove contaminated clothing.
  • Eyes: Rinse cautiously with water for several minutes; remove contact lenses if present and easy to do; seek medical attention if irritation persists.
  • Inhalation: Move to fresh air; monitor for respiratory irritation.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical advice.

• Spill/leak response (general):

  • Contain with inert absorbent (vermiculite, sand), collect in compatible container for disposal. Prevent entry into drains.

Always consult the Aladdin SDS for this SKU for definitive classification, exposure limits, and response measures.

Solvent Selection

This product is a hydrophobic, neutral ester—typically used as a substrate, intermediate, or inert organic phase component rather than as a primary solvent.

• Polarity and miscibility (literature):

  • Nonpolar to weakly polar aprotic character; expected immiscibility with water and good miscibility with hydrocarbons (hexanes, heptane), ethers (Et2O, THF), chlorinated solvents (CH2Cl2), and moderately polar esters (EtOAc).
  • Low dielectric constant expected (<10), similar to other long-chain alkyl/cycloalkyl esters.

• Selection guidance for use as medium or cosolvent (general):

  • For nonpolar reactions or extractions where a high-boiling, inert carrier is desired, consider this ester alongside toluene or long-chain alkanes; the ester functionality provides slightly higher polarity than alkanes which can improve solubility of certain substrates.
  • For catalysis or moisture-sensitive reactions, prefer rigorously dried solvents (e.g., anhydrous toluene, THF). This ester is not typically used as a reaction solvent in air/moisture-sensitive organometallic chemistry.

• Comparison notes (literature trends):

  • Versus toluene: lower aromatic content and odor; higher viscosity and potentially higher bp.
  • Versus ethyl acetate: substantially lower polarity and much lower water miscibility; higher hydrophobic partitioning.

Conclusion: Not a common primary solvent; select standard solvents for kinetics and heat transfer, and reserve this ester as substrate or hydrophobic diluent when its compatibility is advantageous.

Storage and Reconstitution

• Storage conditions (Product Data): Room temperature.

• Shipped in: Not specified for this item; refer to CoA/Spec Sheet.

• General storage guidance for neutral aliphatic esters:

  • Keep container tightly closed in a cool, well-ventilated area away from strong oxidizers and strong acids/bases.
  • Protect from prolonged exposure to moisture to minimize hydrolysis; if long-term storage is planned, consider storing under inert gas and in amber glass to reduce oxidative/byproduct formation.
  • If extremely low hydrolysis background is required, store at 2–8 °C; bring to ambient temperature before opening to prevent condensation.

• Reconstitution: Delivered as a neat liquid (appearance not specified). If viscosity impedes handling, gently warm to ambient temperature and vortex. For solution preparation, use dry, oxygen-free solvents when required by the application.

• Stability notes (general): Neutral, saturated esters are typically stable for ≥12 months at ambient conditions when protected from moisture and light. Always verify integrity by GC or NMR before critical experiments.

• Research use note: For research use only (per Product Data).

Structure and Identity

Ethyl 3-cyclohexylbutanoate is an aliphatic ethyl ester bearing a secondary carbon substituted with a cyclohexyl ring.

• Item-specific identifiers (Product Data):

  • SKU: E978364
  • Product name: Ethyl 3-cyclohexylbutanoate
  • CAS: 28811-80-5
  • CID: 11041742
  • InChIKey: 143984 (as provided)
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.

• Computed/literature structural information (for reference):

  • Molecular formula (derived from name): C12H22O2 (literature/computed)
  • Molecular weight: ~198.30 g/mol (literature/computed)
  • Possible SMILES (literature): CCOC(=O)CC(C1CCCCC1)C
  • Functional groups: ethyl ester (–CO2Et), saturated cycloalkyl (cyclohexyl), saturated aliphatic chain.
  • Stereochemistry: The 3-position (β-carbon to the carbonyl) is a stereogenic center; material may be racemic unless otherwise specified.

• 2D structural description (general):

  • An ethyl ester carbonyl (EtO–C(=O)–) is followed by a two-carbon butanoate chain. The β-carbon (relative to the carbonyl) is a methine bearing a cyclohexyl substituent and a methyl group, terminating in a saturated backbone. No heteroatoms beyond the ester oxygen atoms; ring system is a single cyclohexane.

Synthetic Utility

Ethyl 3-cyclohexylbutanoate provides a sterically encumbered, saturated ester motif, valuable for probing steric effects and constructing hindered aliphatic frameworks.

• Retrosynthetic handle:

  • The ester can be hydrolyzed to 3-cyclohexylbutanoic acid, then diversified via amide coupling, Curtius rearrangement (to isocyanate), or conversion to acid chlorides for acylations.
  • Reduction furnishes the corresponding primary alcohol, enabling further oxidation-state manipulations (tosylation → substitution; oxidation to aldehyde/acid).

• Functional group reactivity (literature):

  • Enolate chemistry at the α-methylene: LDA/THF at −78 to −20 °C enables alkylation, though β-secondary substitution reduces enolate formation rate and can favor kinetic control.
  • Radical or photochemical functionalization at the tertiary C–H sites on the cyclohexyl ring (e.g., benzylic-like positions absent; C–H activation may require catalysts and strong HAT reagents).
  • Selective transesterification with bulky alcohols can be used to generate sterically tuned esters for enzymatic selectivity studies.

• Scaffold applications:

  • A lipophilic appendage in fragment-to-lead campaigns or probe molecules where a neutral, metabolically cleavable ester is desired.

This compound is especially suited for exploring steric impacts on acyl transfer, ester hydrolysis kinetics, and phase behavior in nonpolar media.

Target Specificity

Not applicable. This product is a small-molecule ester, not a biological targeting reagent (e.g., antibody, ligand with defined biomolecular target). No antigen, epitope, or species reactivity data are associated with this SKU.