Ethyl 6-oxodecanoate , CAS No.4144-61-0

CAS: 4144-61-0 Cat. No.: E1016515 Formula: C₁₂H₂₂O₃ Peso molecolare: 214.31 PubChem CID: 11063798

Storage

Room temperature

Specifications

Condizioni di conservazione di stoccaggio

Room temperature

Nomi e identificatori

• Sorrisi canonici: CCCCC(=O)CCCCC(=O)OCC
• IUPAC Name: ethyl 6-oxodecanoate
• InChIKey: ABYZTYKKLSUMLT-UHFFFAOYSA-N
• INCHI: 1S/C12H22O3/c1-3-5-8-11(13)9-6-7-10-12(14)15-4-2/h3-10H2,1-2H3
• Isomeri SMILES: CCCCC(=O)CCCCC(=O)OCC
• PubChem CID: 11063798
• Peso molecolare: 214.31

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 acyclic 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 acyclic 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: 214.300 g/mol
• XLogP3: 2.200
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 10
• Exact Mass: 214.157 Da
• Monoisotopic Mass: 214.157 Da
• Topological Polar Surface Area: 43.400 Ų
• Heavy Atom Count: 15
• Formal Charge: 0
• Complexity: 187.000
• 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

No assay or immunoassay application data are provided for this small-molecule reagent. Typical laboratory uses follow standard organic synthesis workflows. For practical procedures, see the Reaction Conditions tab and adapt stoichiometry, solvent, and temperature to your specific transformation.

Biological Roles

This product is supplied for research use only. Ethyl 6-oxodecanoate is a synthetic aliphatic keto ester without a known intrinsic biological role.

• General notes (literature context):
  • Structurally related to medium-chain lipid analogs; hydrophobic tail with polar carbonyls can influence membrane partitioning in model systems.
  • May serve as a scaffold to prepare lipidated probes or ester pro-moieties in biochemical tool compounds; biological activity, if any, depends on the downstream structure, not on this intermediate itself.

No endogenous metabolic function or pathway assignment is associated with Ethyl 6-oxodecanoate itself. Do not use for diagnostics or clinical applications.

Buffer Applications

Not typically applicable. Ethyl 6-oxodecanoate is a neutral, hydrophobic organic building block and is not used as a buffering agent. For aqueous work, choose an appropriate biological buffer (e.g., phosphate, HEPES) and conduct organic-phase manipulations as described in Solvent Selection and Reaction & Applications.

Green Alternatives

Greener tactics focus on solvent and reagent selection when using Ethyl 6-oxodecanoate.

• Solvent choices (comparative, literature):

  • THF → 2-MeTHF or CPME (renewable origin, higher boiling points, lower peroxide rates than Et2O; good for enolizations and reductions).
  • CH2Cl2 → EtOAc or dimethyl carbonate (DMC) for extractions and some reactions (reduced halogenated waste; check solubility and reaction compatibility).
  • DMF/DMSO → Cyrene or propylene carbonate where feasible (lower toxicity; consider base compatibility and workup ease).

• Reagent alternatives:

  • NaBH4 reductions in green alcohols (EtOH, i-PrOH) rather than in MeOH/THF blends; catalytic hydrogenation with H2 replaces stoichiometric hydrides where selectivity allows.
  • Organocatalytic aldolizations (e.g., proline derivatives) or biocatalytic reductions (ketoreductases) as alternatives to metal-based catalysts; ensure compatibility with the ester.

• Workup/processing:

  • Use aqueous ethanol or isopropanol for phase-splitting instead of chlorinated solvents when possible.
  • Implement solvent recycling for toluene/EtOAc/heptane systems.

Trade-offs: Greener solvents may alter enolate geometry, rate, and selectivity; CPME and 2-MeTHF can change reduction chemoselectivity compared with THF or Et2O. Always pilot small-scale trials to validate performance.

Pharmaceutical Uses

For research use only. No pharmacopeial grade is specified for this item; refer to CoA/Spec Sheet.

• Formulation/excipient role: Not commonly used directly as an excipient. However, as a bifunctional intermediate, it can be leveraged in medicinal chemistry to construct ester-containing prodrugs or lipidated analogs, where the ketone enables selective derivatization (e.g., reductive amination) prior to final deprotection or hydrolysis steps (literature context).
• Process considerations:
  • Residual solvents and acid/base impurities can impact downstream API steps (e.g., catalytic hydrogenations or enolate alkylations). Validate impurity profiles per ICH Q3A/Q3C in development settings.
  • Hydrolytic stability should be assessed during scale-up; control pH and water content during storage and reaction staging.

No therapeutic claims are made. This item is intended for synthetic use in preclinical research and process development.

Physical Properties

Item-specific specifications

• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
• 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/estimated values (typical for this substance; not product specifications)

• Molecular formula (literature): C12H22O3
• Molecular weight (literature): ~214.30 g/mol
• Physical state: Typically a colorless to pale yellow liquid (literature generalization for mid-chain keto esters).
• Boiling point: Often >250 C at 760 mmHg; commonly distilled at reduced pressure, e.g., 120–160 C at 1–5 mmHg (literature ranges for C12 aliphatic keto esters).
• Melting point: Likely below 0 C (literature expectation for similar aliphatic esters).
• Density: Approx. 0.97–1.00 g/mL at 20–25 C (literature for comparable ethyl esters with an extra carbonyl).
• Refractive index (nD20): Approximately 1.440–1.450 (literature estimate for long-chain esters/keto esters).
• Solubility: Low in water; miscible with many organic solvents (Et2O, EtOAc, CH2Cl2, toluene, THF) (literature).
• LogP: Expected moderately lipophilic (estimated cLogP ~2.5–3.5 for C12 keto esters; literature/estimated).

Note: Values above are provided as general reference. For lot-specific specifications and acceptance criteria, consult the CoA/Spec Sheet.

Quality and Grades

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

Guidance on grades (general information)

• Research grade organic building blocks are typically supplied at high purity suitable for synthesis and method development. Where stated, GC/HPLC area % and residual solvent/water/by-metal limits define usability for sensitive steps.
• If HPLC or GC assay is provided on the CoA, confirm acceptance criteria against your process needs (e.g., for enolate chemistry or catalytic hydrogenation, peroxides and acidic impurities should be minimal).
• UV-Vis properties (for chromatographic detection) and residual water are relevant for process control but are not specified here; consult the CoA if these are critical to your application.

Implications for this compound type

• Keto esters are prone to slow hydrolysis and self-condensation under basic or acidic conditions. Trace acid/base impurities and storage history can influence color and assay over time. Review the CoA for acid value, water content, and assay prior to use in base-sensitive steps.

Reaction and Applications

With both an internal ketone and a terminal ethyl ester, Ethyl 6-oxodecanoate is a versatile bifunctional building block.

• Selective reductions (literature):
  • NaBH4 or catalytic hydrogenation can reduce the ketone selectively to the secondary alcohol, retaining the ester under controlled conditions.
  • DIBAL-H or LiAlH4 enables deeper reductions (e.g., to diols or to the corresponding diol/primary alcohol after ester reduction), depending on stoichiometry and temperature.
• Carbon–carbon bond formations:
  • Enolate chemistry at the α-positions of either the ketone or the ester (LDA/LHMDS) allows regioselective alkylation or aldol-type condensations. Employ silyl enol ether formation for cross-aldol couplings.
  • Intramolecular cyclizations via Dieckmann (ester enolate) or Claisen variants can produce macro- or medium-sized rings, leveraging the internal ketone as electrophile.
• Oxidations/functional group interconversions:
  • Baeyer–Villiger oxidation of the ketone to an internal ester/lactone motif.
  • Chemoselective acetal formation at the ketone for protection during downstream ester transformations.
• Heteroatom installations:
  • Reductive amination at the ketone provides ω-ester–substituted secondary/tertiary amines useful in lipid and surfactant synthesis.
• Applications context:
  • Useful intermediate for making medium-chain functionalized lipids, fragrances, specialty monomers, and probes where spatial separation of two carbonyls is required for orthogonal chemistry.

Practical tips: Control temperature and base to direct enolate formation (ketone enolates form with weaker base than ester enolates). Protect sensitive carbonyl when executing strongly basic or acidic transformations.

Reaction Conditions

General guidance (from literature for aliphatic keto esters; optimize per your route):

• Selective ketone reduction:
  • NaBH4 (1.1–1.5 equiv) in MeOH, EtOH, or i-PrOH, 0–25 C, 0.5–2 h → secondary alcohol with ester retained; quench with NH4Cl. Diastereoselectivity is irrelevant here (acyclic substrate).
  • Catalytic hydrogenation (H2, 1–5 bar) over Pd/C in EtOAc or EtOH, 20–40 C, 2–6 h can reduce the ketone; monitor to avoid over-reduction of the ester.
• Enolate formation/alkylation:
  • LDA (1.1–1.5 equiv) in dry THF, −78 to −40 C, 0.5–1 h preformation, then add alkyl electrophile (R–X) at ≤−40 C; warm to 0 C. Compete with ketone enolate if not protected.
  • For ketone-directed aldol: TiCl4 or BF3·OEt2 activation of silyl enol ethers in CH2Cl2 at −78 to 0 C.
• Reductive amination (ketone site):
  • Amine (1.2–2.0 equiv), NaBH(OAc)3 in DCE or MeOH, 0–25 C, 1–6 h; or H2/Pd-C with preformed imine; maintain neutral-to-slightly acidic conditions to preserve ester.
• Baeyer–Villiger oxidation:
  • mCPBA (1.5–2.0 equiv) in CH2Cl2, 0–25 C, 2–16 h; or H2O2/formic acid systems (caution: exotherm). Workup with bicarbonate.

Typical isolated yields for well-optimized steps are 70–90%, but are substrate- and condition-dependent. Conduct small-scale scouting to establish chemoselectivity between the two carbonyl functions.

Safety and Handling

Item-specific hazard statements (from Product Data)

• Signal word: Not specified; refer to SDS.
• H-statements: Not specified; refer to SDS.
• GHS classification/pictograms: Not specified; refer to SDS.

General safety guidance for aliphatic keto esters (literature/industry practice; not a substitute for SDS)

• Likely hazards: Combustible liquid; may cause skin/eye irritation and respiratory irritation if aerosolized. Avoid inhalation of vapors and prolonged skin contact.
• Personal protective equipment: Use lab coat, safety glasses or chemical splash goggles, and appropriate disposable nitrile gloves. Employ in a fume hood to minimize vapor exposure.
• Incompatibilities: Strong bases (risk of ester hydrolysis and enolate formation), strong acids (acid-catalyzed hydrolysis), strong oxidizers (oxidation of organic substrate), and strong reducing agents (may reduce carbonyl groups). Avoid moisture for long-term stability.
• Spill/cleanup: Absorb with inert material (vermiculite, sand), collect in suitable container for disposal. Ventilate area; avoid ignition sources.
• First aid overview: If on skin, wash with soap and water; remove contaminated clothing. If in eyes, rinse cautiously with water for several minutes. If inhaled, move to fresh air. If ingested, rinse mouth; seek medical advice. Always follow the SDS for authoritative instructions.
• Fire-fighting: Use dry chemical, CO2, or alcohol-resistant foam. Combustion can produce CO and CO2.

Always defer to the product-specific SDS for definitive hazard classification, exposure limits, and emergency procedures.

Solvent Selection

Ethyl 6-oxodecanoate is a neutral, moderately lipophilic, aprotic organic substrate.

• Polarity/miscibility (literature/general): Insoluble or sparingly soluble in water; miscible with many organic solvents (Et2O, EtOAc, CH2Cl2, THF, toluene, hexanes to a limited extent due to polarity from dual carbonyls).
• Dielectric behavior: Expected low-to-moderate polarity; polar aprotic media (THF, DMF, DMSO) enhance enolate chemistry, while nonpolar solvents (toluene, heptane) are suitable for reductions/hydrogenations where solubility allows.
• Chromatography: Elutes with medium polarity eluents (e.g., hexanes/EtOAc 7:3 to 4:6). Monitor by TLC with UV (weak) and carbonyl staining (2,4-DNP).
• When to choose solvents:
  • Enolate formation/alkylation: Dry THF, MTBE, or CPME at −78 to 0 C (with LDA/LHMDS).
  • Selective ketone reduction: Alcoholic solvents (i-PrOH, MeOH) with NaBH4 can reduce the ketone faster than the ester; use THF/MeOH mixtures to tune chemoselectivity.
  • Baeyer–Villiger or oxidation chemistry: CH2Cl2 or acetonitrile often preferred.
  • Hydrogenation: Alcohols or toluene under H2 with Pd/C or Raney Ni, depending on target.
• Practical tip: Rigorous drying of solvent is advised for base-catalyzed steps to prevent hydrolysis of the ester.

Storage and Reconstitution

Item-specific (from Product Data)

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

General guidance for this compound class

• Keep container tightly closed in a dry, well-ventilated place. Minimize exposure to moisture and strong acids/bases to limit hydrolysis and self-condensation.
• If long-term storage is anticipated, consider storing under inert gas (nitrogen/argon) and in amber glass to reduce potential oxidative discoloration. Avoid prolonged exposure to elevated temperatures.
• Reconstitution: Not applicable; typically supplied as a neat liquid. If solidified at low temperature, gently warm to ambient and mix thoroughly before use.
• After opening: Record open date; for moisture-sensitive enolate chemistry, verify water content or assay prior to critical steps.

Always consult the product’s CoA and SDS for any lot-specific storage and handling instructions.

Structure and Identity

Item-specific (from Product Data)

• Product name: Ethyl 6-oxodecanoate
• CAS: 4144-61-0
• PubChem CID: 11063798
• InChIKey: 1467 (as provided)
• Storage: Room temperature

Computed/literature structural information (for reference; verify against CoA/SDS)

• Common description: A linear aliphatic β-keto ester analogue separated by a four-methylene spacer from the ester carbonyl (i.e., an ethyl decanoate bearing a ketone at C6).
• Functional groups: One terminal ethyl ester (–CO2Et) and one internal ketone (–CO–) on a saturated C10 chain; overall neutral, non-aromatic; no stereocenters.
• Typical SMILES (literature): CCOC(=O)CCCC(=O)CCCC
• Empirical formula (literature): C12H22O3
• Molecular weight (literature): ~214.30 g/mol

2D structural description in words

• An ethyl ester carbonyl at one end is connected to a polymethylene chain of four –CH2– units, followed by a ketone carbonyl, and then a three-methylene segment terminating in a methyl group. The molecule is fully saturated, linear, and achiral, with two electrophilic carbonyl centers enabling chemoselective transformations.

Synthetic Utility

Key reactivity derives from the presence of two electrophilic carbonyls separated by a (CH2)4 spacer.

• Orthogonal carbonyl chemistry:
  • Protect the ketone as an acetal/ketal, then manipulate the ester (hydrolysis, amidation, reduction) without perturbing the protected site.
  • Alternatively, form a silyl enol ether at the ketone for Mukaiyama aldol reactions while leaving the ester intact.
• Enolate control:
  • Ketone α-enolate forms with weaker bases (NaOEt, t-BuOK) at 0–25 C; ester α-enolate typically requires strong, non-nucleophilic bases (LDA/LHMDS) at −78 to −20 C. Chelating conditions and HMPA alternatives (e.g., DMPU) can tune regioselectivity.
• Ring constructions:
  • Intramolecular aldol (ketone as electrophile) or Dieckmann (ester enolate) cyclizations enable formation of cyclohexanone/cyclopentanone-fused motifs with pendant ester handles.
• Upstream/downstream functional group interconversions:
  • Baeyer–Villiger oxidation of the ketone to an internal ester; subsequent hydrolysis yields diacids or hydroxy acids.
  • Reductive amination at the ketone, followed by ester transformations to access amino-ester surfactants or lipidic linkers.
• Retrosynthetic value:
  • Serves as a convergent handle in sequences where a mid-chain electrophile and a terminal carboxyl derivative must be addressed independently.

Practical note: Scrupulous exclusion of water and acids/bases during storage and handling minimizes background hydrolysis and self-condensation.

Target Specificity

Not applicable. This product is a small-molecule organic building block and is not a biological targeting agent (no antigen/epitope/isotype attributes). No item-specific target data are provided.