Ethyl 8-cyclohexyl-8-oxooctanoate , CAS No.898753-80-5

CAS: 898753-80-5 Cat. No.: E963080 Formula: C₁₆H₂₈O₃ Peso molecolare: 268.397 PubChem CID: 24727431

Storage

Room temperature

Specifications

Condizioni di conservazione di stoccaggio

Room temperature

Nomi e identificatori

Sorrisi canonici

CCOC(=O)CCCCCCC(=O)C1CCCCC1

IUPAC Name

ethyl 8-cyclohexyl-8-oxooctanoate

InChIKey

OQOPHDDUPFVFBB-UHFFFAOYSA-N

INCHI

1S/C16H28O3/c1-2-19-16(18)13-9-4-3-8-12-15(17)14-10-6-5-7-11-14/h14H,2-13H2,1H3

Isomeri SMILES

CCOC(=O)CCCCCCC(=O)C1CCCCC1

PubChem CID

24727431

Peso molecolare

268.397

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: Ketones Carboxylic acid esters Monocarboxylic acids and derivatives Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aliphatic homomonocyclic compounds
• Substituents: Fatty acid ester - Ketone - 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: 268.390 g/mol
• XLogP3: 4.000
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 10
• Exact Mass: 268.204 Da
• Monoisotopic Mass: 268.204 Da
• Topological Polar Surface Area: 43.400 Ų
• Heavy Atom Count: 19
• Formal Charge: 0
• Complexity: 267.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• 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

Application Protocols

Not applicable as an assay reagent like antibodies/enzymes. For synthetic use, follow the Reaction Conditions section. For analytical handling:

• Prepare solutions in suitable organic solvent (e.g., DMSO, EtOAc, DCM, or acetonitrile) at known concentration.
• Analyze by GC–MS (if sufficiently volatile under temperature program) or LC–MS/RI/ELSD. Use appropriate reference standards where quantitation is required.

Biological Roles

This material is a synthetic aliphatic keto-ester with no established endogenous biological role.

• General/literature context

  • Structurally resembles lipid-like molecules (long aliphatic chain, terminal carbonyls), and may serve as a hydrophobic probe or intermediate in the preparation of lipid-mimetic compounds for biochemical studies.
  • The ester linkage can be hydrolyzed enzymatically or chemically to the corresponding acid in model systems; the ketone can undergo biocatalytic reduction to chiral secondary alcohols using ketoreductases (literature precedent for aliphatic ketones).

• Notes

  • No specific metabolic pathway associations or receptor interactions are defined for this exact structure in the research literature.
  • Use is limited to research applications; not intended for diagnostic or therapeutic use.

Buffer Applications

Not typically applicable. Ethyl 8-cyclohexyl-8-oxooctanoate is a hydrophobic organic substrate, not a buffering agent. For experimental work requiring aqueous phase control, select an appropriate buffer system separately (e.g., phosphate, HEPES) and dissolve this compound in a compatible organic co-solvent or formulate as an emulsion/micelle if needed.

Green Alternatives

Although the compound itself is a substrate, greener choices can be made for reaction and processing solvents and reagents.

• Greener solvent swaps (literature guidance)

  • Replace THF with 2-MeTHF (biorenewable, higher boiling, better water tolerance) for reductions and enolate chemistry when compatible.
  • Use CPME in place of MTBE/THF for hydride reductions and extractions (low peroxide formation, broad biphasic stability).
  • Prefer ethyl acetate or isopropyl acetate over DCM/chloroform for workups and chromatography when separation allows.
  • For nonpolar media, heptane/cyclohexane can substitute for hexane mixtures to reduce aromatic content and improve worker exposure profiles.

• Reagent and workup considerations

  • Catalytic hydrogenation (H2/Pd-C) can replace stoichiometric metal hydrides for selective ketone reduction when ester retention is desired and the substrate tolerates hydrogenation.
  • Enzyme-catalyzed resolutions/reductions (ketoreductases) may offer high selectivity for generating chiral secondary alcohols from the ketone (where applicable), in aqueous-organic systems.

• Tradeoffs

  • 2-MeTHF and CPME can change enolate geometry and reaction rates; re-optimize bases/temperatures.
  • Ethyl acetate may co-elute with product in normal-phase chromatography; adjust gradients or switch to reversed-phase if needed.

Pharmaceutical Uses

No pharmacopeial excipient status or formulation role is specified for this item. In a research/manufacturing context, compounds of this type may be used as synthetic intermediates en route to more complex molecules.

• Item-specific note

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

• General considerations (non-clinical)

  • Hydrophobic intermediates like this can be incorporated into prodrug or lipidation strategies during discovery chemistry; any such use requires subsequent purification and full characterization.
  • No therapeutic claims are made or implied. For research use only.

Physical Properties

• Item-specific specifications

  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular Formula: Not specified for this item; refer to CoA/Spec Sheet.
  • Water content, residual solvents, metals, UV cutoffs: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/estimated properties (for general guidance; not product specifications)

  • Approx. formula/mass (from name-derived structure): C16H28O3; ~268.39 g/mol
  • Physical state: expected to be a colorless to pale yellow oily liquid at room temperature (literature expectation for C16 saturated esters/ketones)
  • Density: typically ~0.90–1.00 g/mL for analogous long-chain keto-esters (literature range)
  • Boiling point: high-boiling, likely >300 °C at 1 atm; distillable under high vacuum (literature expectation for C16 esters)
  • Refractive index: commonly nD 20 ~1.44–1.47 for related aliphatic esters/ketones (literature range)
  • Solubility: low in water; miscible with common organic solvents (EtOAc, DCM, toluene, hexanes, THF, MeCN often partially) (general guidance)
  • LogP: expected high (lipophilic), typical of long-chain aliphatic esters/ketones (literature expectation)

• Practical notes

  • Handle as a hydrophobic, high-boiling liquid; use gentle warming to decrease viscosity for accurate pipetting.
  • For analytical QC, GC or HPLC with ELSD/RI/UV (short-wavelength) can be suitable; confirm solvent/gradient compatibility.

Quality and Grades

• Item-specific grade/purity

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

• Interpreting typical grades (general guidance)

  • Research-grade keto-esters are commonly supplied at >95% purity for synthetic applications. If low-UV impurity control is required (e.g., analytical detections), HPLC-grade solvents should be used during handling, but the compound itself is an analyte/intermediate rather than a solvent.
  • If a stabilizer is present (rare for saturated keto-esters), it is usually to suppress hydrolysis or acid-catalyzed side reactions; check the CoA for any additives before using in sensitive catalysis or polymerizations.

• QC considerations

  • Identity/purity confirmation: 1H/13C NMR (characteristic ester and ketone carbonyl signals), IR (approx. 1735–1750 cm−1 for ester C=O; ~1700–1715 cm−1 for ketone C=O), GC–MS/LC–MS.
  • Water/peroxide/metal specs: Not specified for this item; refer to CoA/Spec Sheet. If moisture-sensitive transformations are planned (e.g., enolate chemistry), consider Karl Fischer on receipt.

• Batch documentation

  • For regulated workflows, request CoA/Spec Sheet for this specific lot to obtain exact purity, residual solvents, and analytical data.

Reaction and Applications

Ethyl 8-cyclohexyl-8-oxooctanoate is an ω-keto ester bearing two separable carbonyl functions, enabling diverse chemoselective transformations.

• Representative reaction families (general/literature)

  • Chemoselective reductions: NaBH4 or catalytic hydrogenation reduces the ketone to a secondary alcohol while leaving the ester intact; stronger hydrides (LiAlH4, DIBAL-H at ≥0 °C) reduce the ester (and potentially the ketone) to alcohols.
  • Enolate chemistry: α-deprotonation adjacent to the ketone or ester enables alkylation, aldol, or Michael reactions; kinetic vs thermodynamic enolate control achievable by base, temperature, and solvent choice.
  • Acylation/derivatization: Conversion of the ester to amides via aminolysis; transesterification for isotopic labeling or handle switching.
  • Oxime/hydrazone formation: Carbonyl derivatization at the ketone for purification, protection, or traceless activation to amines (via oxime/hydrazone reduction).
  • Baeyer–Villiger at the ketone (literature): Potential conversion to an ester/lactone motif on the cyclohexyl side, enabling ring-expansion chemistry.

• Strategic uses in synthesis

  • Lipid-mimetic building block for structure–property studies (e.g., tuning hydrophobic tails while retaining a polar head via ester).
  • Precursor to 1,4- or 1,5-diol motifs after stepwise reductions and functional-group interconversions.
  • Handle for tethered intramolecular condensations (e.g., formation of medium-sized rings from keto-ester substrates under enolate/aldol conditions).

• Practical considerations

  • Maintain anhydrous conditions for base-mediated steps; ester hydrolyzes under strong base in protic media.
  • For selective ketone reduction, use NaBH4 in alcoholic/THF solvents at 0–25 °C; quench carefully to avoid saponification.
  • Monitor reactions by IR (loss/shift of ketone vs ester bands) and NMR to track chemoselectivity.

Reaction Conditions

General, literature-informed guidance for typical transformations on ω-keto esters; optimize for your lab scale and substrate.

• Selective ketone reduction (retain ester)

  • Reagent: NaBH4 (1.2–2.0 equiv)
  • Solvent: MeOH, EtOH, or THF/IPA
  • Temp/time: 0–25 °C, 0.5–3 h
  • Notes: Control exotherm on addition; quench with NH4Cl; minimal ester reduction under these conditions.

• Global reduction to diol (reduce ester and ketone)

  • Reagent: LiAlH4 (2–4 equiv) in dry THF
  • Temp/time: 0 °C → reflux, 2–6 h
  • Notes: Work up cautiously (wet ether protocol); expect conversion to a primary and secondary alcohol.

• Ester to aldehyde (partial reduction)

  • Reagent: DIBAL-H (1.1–1.5 equiv)
  • Solvent: dry toluene or CH2Cl2
  • Temp/time: −78 to −40 °C, 1–2 h
  • Notes: Low temperature essential to avoid over-reduction; aqueous Rochelle’s salt quench.

• Enolate alkylation at the ketone α-position

  • Base: LDA (1.1–1.5 equiv) from n-BuLi/diisopropylamine
  • Solvent: dry THF or 2-MeTHF
  • Temp: −78 → −40 °C; slow addition of alkyl halide
  • Notes: Use HMPA-free protocols; monitor by TLC/GC.

• Saponification to acid

  • Reagent: NaOH or K2CO3 in MeOH/H2O or EtOH/H2O
  • Temp/time: 20–50 °C, 1–6 h
  • Notes: Avoid if ketone enolization leads to side reactions; acidify to pH ~2 and extract promptly.

All parameters are general literature guidance; verify on small scale and consult SDS for reagent hazards.

Safety and Handling

• Item-specific safety data

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

• General safety considerations for aliphatic keto-esters (informational; defer to SDS)

  • Hazards: May cause skin/eye irritation; ingestion/inhalation of vapors or aerosols should be avoided. High-boiling organic liquids can form irritating mists.
  • Flammability: Organic ester/ketone mixtures are combustible; although flash points are often elevated for C16 species, keep away from ignition sources.
  • Reactivity/incompatibilities: Sensitive to strong acids/bases (risk of hydrolysis/transesterification); ketone is stable but reacts with strong nucleophiles/reducing agents. Incompatible with strong oxidizers.
  • Peroxide formation: Not generally prone (unlike ethers), but good practice is to store in tightly closed containers and minimize air/UV exposure.

• Recommended PPE and engineering controls

  • Use in a chemical fume hood.
  • Wear lab coat, safety glasses/goggles, and appropriate chemically resistant gloves (e.g., nitrile).

• First-aid overview (general guidance; consult SDS)

  • 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 attention.

• Spill/fire response

  • Absorb small spills with inert material (vermiculite, sand). For fire, use CO2, dry chemical, or foam. Avoid release to drains.

Solvent Selection

This product is a substrate/reagent rather than a solvent. Choice of reaction/processing solvent should reflect the compound’s strong hydrophobicity and dual carbonyl functionality.

• Polarity and miscibility (general expectations)

  • Highly lipophilic; insoluble or sparingly soluble in water.
  • Readily soluble in nonpolar to moderately polar organics: hexanes, toluene, DCM, chloroform, EtOAc, MTBE, CPME, THF, 2-MeTHF. Often dissolves in MeCN with gentle warming.

• Selection guidelines by operation

  • Nucleophilic additions/reductions to the ketone: THF/2-MeTHF, toluene, or DCM under anhydrous conditions; for hydride reductions, THF or IPA/toluene blends can be effective depending on reagent.
  • Hydrolysis/transesterification: Alcoholic solvents (MeOH, EtOH) under acid/base catalysis; consider azeotropic water removal for equilibrium-driven steps.
  • Enolate generation/alkylation: Dry THF, CPME, or toluene with HMPA-free alternatives (DME, DMI) as needed; strictly anhydrous, inert atmosphere.
  • Chromatography/workup: Hexanes/EtOAc gradients typically provide good resolution; add small DCM fractions to aid elution of viscous fractions.

• Practical tips

  • Warm slightly (30–40 °C) or use small DCM/EtOAc co-solvent to reduce viscosity for accurate volumetric handling.
  • Avoid prolonged exposure to alcoholic solvents with base if ester integrity must be preserved.

Storage and Reconstitution

• Item-specific storage

  • Storage Conditions: Room temperature (as provided). Store tightly closed in a dry, well-ventilated place away from heat and direct sunlight.
  • Shipped In: Not specified for this item; refer to CoA/Spec Sheet.

• Handling and solution preparation

  • Keep container tightly sealed to minimize adventitious hydrolysis. If long-term storage is planned, consider aliquoting under inert gas.
  • For stock solutions, dissolve in dry organic solvents (e.g., DCM, THF, toluene, EtOAc, MeCN, or anhydrous ethanol). For biological assays, DMSO stocks are common; confirm compatibility.
  • Typical concentration ranges: 10–200 mg/mL depending on solvent viscosity and solubility; filter if particulate forms.

• Stability notes (general)

  • Stable under ambient conditions when dry. Avoid strong acids/bases and prolonged exposure to moisture or alcohols if ester integrity is required.
  • Do not freeze aqueous mixtures; phase separation/hydrolysis may occur upon thawing.

• Research Use Only

  • For research use only. Not for human or veterinary use.

Structure and Identity

Ethyl 8-cyclohexyl-8-oxooctanoate is a hydrophobic aliphatic keto-ester featuring a terminal cyclohexyl ketone at the ω-end of an octanoate chain and an ethyl ester at the carboxyl end.

• Item-specific identifiers (from Product Data)

  • SKU: E963080
  • Product Name: Ethyl 8-cyclohexyl-8-oxooctanoate
  • CAS: 898753-80-5
  • CID: 24727431
  • InChIKey: 264808 (as provided)
  • Storage: Room temperature
  • Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/computed structural information (informational; non-authoritative)

  • Molecular formula (inferred from name): approximately C16H28O3
  • Approx. molecular weight: ~268.39 g/mol (computed from inferred formula)
  • SMILES (derived from name; non-authoritative): CCOC(=O)CCCCCC(=O)C1CCCCC1
  • Functional groups: ethyl ester (–CO2Et), saturated aliphatic chain, aryl-free cyclohexyl ketone (–CO–C6H11)
  • Structural features (2D description): an ethyl ester carbonyl at one terminus connects to a six-methylene spacer (–(CH2)6–), terminating in a ketone carbonyl bonded to a cyclohexyl ring; no pi-systems or heteroatoms beyond three oxygens; no stereocenters.

• Notes

  • Where exact identifiers (e.g., authoritative InChI/SMILES, formula, MW) are required for regulatory or analytical purposes, consult the product’s CoA/Spec Sheet or generate from a verified structure.

Synthetic Utility

• Functional group portfolio

  • Ketone (cyclohexyl ketone): Enables nucleophilic additions (RMgX/RLi, cyanation), reductive transformations (NaBH4, catalytic hydrogenation), and protection/activation via oxime/hydrazone or acetal (under acidic conditions; avoid ester hydrolysis).
  • Ethyl ester: Amenable to saponification to the acid, transesterification, aminolysis to amides, and reduction to alcohols (DIBAL-H/LiAlH4) with selectivity control.

• Strategic applications

  • Divergent synthesis: Orthogonal reactivity allows stepwise, chemoselective modification—e.g., reduce ketone → functionalize alcohol → convert ester to acid/amide.
  • Tethered dicarbonyl chemistry: The (CH2)6 spacer permits intramolecular condensations after selective activation, enabling medium-ring formation or bicyclic scaffolds.
  • Late-stage diversification: Install handles (azide, halide) at α-positions via enolate chemistry, then perform SN2, click, or cross-coupling after further derivatization.

• Retrosynthetic value

  • Disconnection at the ketone suggests acylation of cyclohexane derivatives with a ω-oxo acyl equivalent; alternatively, assemble via alkylation of a cyclohexanone-derived enolate with an ω-halo-ester followed by oxidation.

• Practical notes

  • Use non-nucleophilic bases (LDA, LiHMDS) for enolate generation to avoid ester transesterification; keep temperatures ≤ −78 to −20 °C for kinetic control.
  • If maintaining ester integrity, avoid prolonged exposure to strong base in protic solvents; quench carefully and extract promptly.

Target Specificity

Not applicable. This product is a small-molecule keto-ester, not a biologic or affinity reagent. No antigen, epitope, or isotype information applies.

Domande frequenti

How should this product be stored?

Store at room temperature.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 898753-80-5, the molecular formula is C16H28O3, and the molecular weight is 268.397 g/mol. InChIKey OQOPHDDUPFVFBB-UHFFFAOYSA-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.