Ethyl 7-oxododecanoate - ≥95% , CAS No.58262-36-5

CAS: 58262-36-5 Cat. No.: E957399 Formule: C₁₄H₂₆O₃ Poids moléculaire: 242.36 PubChem CID: 14250398

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

Spécifications et pureté

≥95%

Conditions de stockage de stockage

Room temperature

Pureté

≥95%

Noms et identifiants

• Sourires canoniques: CCCCCC(=O)CCCCCC(=O)OCC
• IUPAC Name: ethyl 7-oxododecanoate
• InChIKey: ZJBYNRAELGEYLE-UHFFFAOYSA-N
• INCHI: 1S/C14H26O3/c1-3-5-7-10-13(15)11-8-6-9-12-14(16)17-4-2/h3-12H2,1-2H3
• Isomères SMILES: CCCCCC(=O)CCCCCC(=O)OCC
• PubChem CID: 14250398
• Poids moléculaire: 242.36

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
• Description: 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

Propriétés chimiques et physiques

• Poids moléculaire: 242.350 g/mol
• XLogP3: 3.200
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 12
• Exact Mass: 242.188 Da
• Monoisotopic Mass: 242.188 Da
• Topological Polar Surface Area: 43.400 Ų
• Heavy Atom Count: 17
• Formal Charge: 0
• Complexity: 212.000
• 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 validated bioassay or immunoassay protocols are associated with this small-molecule building block.

General lab procedures (illustrative, literature-style; adjust to your needs):

• TLC analysis: Silica gel, hexanes:EtOAc 8:2 as a starting system; visualize with KMnO4 or UV (210–220 nm) due to carbonyl chromophores.
• Column chromatography: Begin at 9:1 hexanes:EtOAc; increase polarity as needed until Rf ~0.3–0.4.
• NMR sample prep: 10–20 mg/mL in CDCl3; carbonyl signals expected near δ 2.1–2.5 ppm (allylic-type methylenes) and 13C carbonyls at ~173–175 ppm (ester) and ~205–210 ppm (ketone) in literature for similar compounds.
• GC/LC: For GC, use non-polar columns with temperature ramp to accommodate mid-high bp. For LC, C18 reverse-phase with MeCN/H2O (isocratic or gradient). These are general practices, not item-specific validations.

For any specialized application, develop and validate your own SOPs.

Biological Roles

This product is intended for research use as a synthetic intermediate. No biological function is assigned to this catalog item.

General context (literature):

• Structural analogy: Medium-chain oxo-fatty esters resemble derivatized lipids; in vivo, related free acids (not ethyl esters) can arise in fatty acid metabolism. However, ethyl esters are typically pro-chemical forms used in synthesis and do not reflect native metabolites.
• Experimental utility: The hydrophobic chain and carbonyl pattern can be used to construct lipid-mimetic probes, membrane-anchoring motifs, or to study partitioning in model membranes after appropriate conversion to target structures.

Important: No medical, diagnostic, or therapeutic use is implied. Any exploration of biochemical interactions should employ appropriate controls and consider that the ethyl ester may require hydrolysis to the free acid to emulate physiological counterparts.

Buffer Applications

Not typically applicable. Ethyl 7-oxododecanoate is a hydrophobic organic building block and is not used as a buffering agent. For experimental work involving this compound, select an appropriate organic or biphasic solvent system and consult the Solvent Selection and Reaction Conditions sections.

Green Alternatives

While Ethyl 7-oxododecanoate is a substrate rather than a solvent, greener choices can be made for its synthesis, processing, and purification.

• Greener solvent options (where compatible):
  • Replace CH2Cl2 with EtOAc, MeTHF, or CPME for extractions and reactions.
  • Favor alcohols (EtOH, iPrOH) or water/MeCN mixtures over DMF/DMSO when feasible.
• Oxidation/reduction choices:
  • Use catalytic hydrogenation or transfer hydrogenation (e.g., Ru, Ir, or organocatalysts with isopropanol) instead of stoichiometric metal hydrides.
  • For Baeyer–Villiger, consider H2O2 with biocatalysts or organocatalysts instead of peracids, reducing waste and hazards.
• Biobased feedstocks:
  • Sourcing from fatty acid derivatives (e.g., lauric acid from plant oils) can improve sustainability metrics for the carbon backbone; install the internal ketone via selective oxidation.

Comparison (general guidance):

• CH2Cl2 vs EtOAc: EtOAc has lower toxicity and is bio-derived; may require longer reaction times or different catalysts but often adequate for carbonyl chemistry.
• THF vs 2-MeTHF: 2-MeTHF is partially bio-based, forms fewer peroxides, and enables biphasic workups; solubility may differ, and low-temperature behavior should be verified.

Note: Optimize green substitutions case-by-case to maintain selectivity (ester vs ketone) and yield.

Pharmaceutical Uses

No excipient or pharmacopeial status is specified for this item; refer to CoA/Spec Sheet. This product is supplied strictly for research use only.

General formulation context (literature/practice):

• Lipidic motif synthesis: The C12-derived chain can be elaborated to lipid-like excipients (e.g., esters, amides) following further functionalization. The internal ketone and terminal ester offer orthogonal handles for diversification.
• Pro-molecule intermediates: Ethyl esters are sometimes used as masked acids during multi-step synthesis to improve solubility and handling before hydrolysis to the free acid; suitability depends on route design and is not a therapeutic claim.
• Stability considerations: For any use in formulation development research, evaluate hydrolysis in aqueous/acidic/basic media, oxidative stability of the ketone, and compatibility with surfactants or oils.

Note: Do not use for human or veterinary applications. All claims of suitability must be validated experimentally under your specific development conditions.

Physical Properties

Item-specific (from Product Data)

• 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/general values (non-item-specific; for planning only)

• Estimated molecular formula (literature): C14H26O3 (ethyl 7-oxododecanoate)
• Estimated molecular weight (literature): ~242.36 g/mol
• Physical state at ambient: Typically a hydrophobic liquid for similar C14 keto-esters (literature expectation; verify on receipt).
• Solubility: Expected low solubility in water; miscible with common organic solvents (e.g., Et2O, CH2Cl2, toluene, THF, MeOH) to varying degrees (literature trend for medium-chain esters).
• LogP: Anticipated high (≫2) due to long alkyl chain (literature trend).
• Refractive index, density, boiling/melting points, UV cutoff: Not specified for this item; consult literature or determine experimentally under your conditions.

Practical notes (general chemistry)

• Volatility: Lower than short-chain esters; suitable for work under standard pressure without excessive loss.
• Hydrolytic sensitivity: Ester function may hydrolyze under strong acidic/basic aqueous conditions; minimize prolonged exposure to moisture if purity is critical.

Quality and Grades

Item-specific (from Product Data)

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

General guidance on grades (context for users)

• Research grade materials are typically suitable for synthetic and analytical R&D. If HPLC/GC analysis is planned, consider pre-testing UV background and GC baseline.
• If a high-purity grade is provided on the CoA, expect lower levels of volatile/acid/base impurities that could interfere with sensitive transformations (e.g., enolate chemistry, asymmetric catalysis).
• For chromatography-critical work, “HPLC grade” solvents and eluents should be used in conjunction with this substrate; the substrate itself may have a normal UV profile for aliphatic carbonyls (verify by UV–vis).
• Trace specifications (water, peroxides, metals, residual solvents) are application-dependent and should be verified on the item’s CoA when available.

Reaction and Applications

Ethyl 7-oxododecanoate combines an internal ketone with a terminal ethyl ester, enabling orthogonal reactivity across a medium-chain scaffold.

• Enolate chemistry at the ketone:
  • Aldol additions with aldehydes/ketones to extend chain or introduce stereocenters (use LDA, LiHMDS, or organocatalysts; control at –78 to 0 °C in dry THF).
  • Michael donors after formation of silyl enol ethers or enolates to add into activated alkenes.
• Chemoselective reductions:
  • NaBH4 or catalytic hydrogenation can reduce the ketone to secondary alcohols while retaining the ester. For ester reduction (to diol or alcohol), use LiAlH4, DIBAL-H (low temp), or borane reagents with appropriate selectivity.
• Oxidations and rearrangements:
  • Baeyer–Villiger oxidation of the internal ketone can generate distal esters/lactones; migratory aptitude and chain topology dictate product distribution.
• Macrocyclizations/lactonizations:
  • Intramolecular esterification after selective functionalization can yield medium rings; the internal ketone can be leveraged for further diversification (e.g., acetal protection, Wittig olefination to install internal alkenes).
• Functional group interconversions:
  • Transesterification to tune the alcohol leaving group (Me, iPr, benzyl). Kinetic vs thermodynamic control by catalyst/temperature.
• Applications:
  • Precursor to tailored surfactants, lipid-like probes, and hydrophobic motifs in materials or chemical biology tools (research use only). The modular chain length and dual carbonyls support rapid analog generation.

Reaction Conditions

General, literature-style conditions for common transformations of keto-esters like Ethyl 7-oxododecanoate (optimize for your substrate):

• Ketone reduction (chemoselective):
  • NaBH4 (1–2 equiv) in MeOH or EtOH, 0–25 °C, 0.5–2 h; typically reduces ketone preferentially over ester. Quench with NH4Cl.
  • Catalytic hydrogenation (Pd/C, 5–10 wt%) in EtOH at 1–5 bar H2, rt–40 °C to obtain secondary alcohol.
• Ester reduction:
  • DIBAL-H (1.5–2 equiv) in toluene or CH2Cl2 at –78 to –20 °C to afford the corresponding aldehyde (from ester) while retaining/controlling ketone; careful quench required.
  • LiAlH4 (2–4 equiv) in THF at 0–25 °C for full reduction to diols; ketone also reduced.
• Enolate/aldolization:
  • LDA (1.1–1.5 equiv) in dry THF at –78 °C, then add electrophile; warm to –20–0 °C. Typical times 0.5–2 h after addition.
• Baeyer–Villiger oxidation:
  • mCPBA (1.2–2.0 equiv) in CH2Cl2 at 0–25 °C, 2–16 h; or H2O2 with catalytic acids in MeCN/EtOAc as greener alternative. Monitor for over-oxidation/hydrolysis.
• Transesterification/hydrolysis:
  • Acidic (p-TsOH, catalytic) or basic (NaOMe) in corresponding alcohol at reflux (2–12 h). For saponification, NaOH/KOH in MeOH/H2O, 0–25 °C, then acidify.

Note: Reported yields for analogous substrates commonly range 60–90% with proper optimization; actual results depend on scale, purity, and workup.

Safety and Handling

Item-specific (from Product Data)

• GHS classification, signal word, pictograms, H-statements: Not specified for this item; refer to SDS.
• Storage conditions: Room temperature.

General safety guidance (defer to SDS for authoritative data)

• Likely hazards (by analogy to aliphatic esters/ketones): Combustible liquid, may cause skin/eye irritation. Avoid inhalation of mists/vapors and prolonged skin contact.
• PPE: Safety glasses or splash goggles, lab coat, appropriate chemical-resistant gloves (e.g., nitrile), and use in a fume hood to control vapors/aerosols.
• Incompatibilities: Strong oxidizers (risk of exotherm/oxidation), strong bases or acids (can promote ester hydrolysis/transesterification), and strong reducing agents for the ketone.
• First aid overview: Skin—wash with soap and water. Eyes—rinse cautiously with water for several minutes and seek medical attention if irritation persists. Inhalation—move to fresh air; obtain medical advice if symptoms occur. Ingestion—rinse mouth; do not induce vomiting; seek medical attention.
• Spill/Fire: Absorb small spills with inert material (vermiculite), dispose per regulations. For fire, use CO2, dry chemical, or foam; cool containers with water spray.
• Waste: Collect as organic waste. Follow institutional and local regulations.

Solvent Selection

This product is a hydrophobic keto-ester building block, not a laboratory solvent. Solvent choice pertains to its use in reactions, purifications, and analyses.

• Polarity and miscibility (general trends):
  • Poorly soluble in water; high solubility in nonpolar to moderately polar organics (hexanes, toluene, Et2O, CH2Cl2, THF). Limited but useful solubility in alcohols (MeOH, EtOH) for transesterification or reductions.
• Reaction media suggestions (general):
  • Base-mediated enolizations/aldolizations: THF, toluene, or DME (dry, inert atmosphere).
  • Reductions (NaBH4, hydrosilanes): MeOH/EtOH (NaBH4) or CH2Cl2/THF (catalytic hydrosilane/transfer hydrogenation).
  • Baeyer–Villiger oxidations: CH2Cl2, CH3CN, or greener MeOAc/EtOAc when compatible.
  • Hydrolyses/transesterifications: MeOH/EtOH with acid/base catalysts; remove alcohol by-product to drive equilibria.
• Purification:
  • Normal-phase silica gel with hexanes/EtOAc gradients is typical. The internal ketone imparts modest polarity; start around 9:1 to 7:3 hexanes:EtOAc and adjust by TLC.
• Analytical solvents:
  • GC: Non-polar capillary columns; ensure absence of labile impurities. LC: C18 reversed-phase with MeCN/H2O or MeOH/H2O; detect by UV at 210–220 nm (literature practice for aliphatic carbonyls).

Storage and Reconstitution

Item-specific (from Product Data)

• Storage conditions: Room temperature.

General handling guidance

• Container: Store in a tightly sealed amber glass vial/bottle to limit moisture and light exposure. Although aliphatic keto-esters are generally stable, minimizing air/moisture ingress preserves assay purity.
• Atmosphere: Inert gas blanket (N2 or Ar) recommended for long-term storage, especially after opening.
• Stability considerations: Avoid strong acids/bases and oxidizers. Prolonged contact with aqueous media may promote ester hydrolysis.
• Freeze–thaw: Not applicable to neat liquids; if preparing stock solutions, aliquot to minimize repeated warming/cooling cycles.
• Reconstitution/solution prep: Dissolves readily in common organic solvents (e.g., CHCl3, CH2Cl2, EtOAc, THF, toluene). Prepare solutions fresh when possible; for longer storage, keep sealed under inert gas at 2–8 °C and verify concentration by weight or quantitative NMR as needed.

Always consult the product CoA/SDS for definitive stability and handling instructions for the specific lot received.

Structure and Identity

Item-specific (from Product Data)

• Product name: Ethyl 7-oxododecanoate (SKU: E957399)
• CAS: 58262-36-5
• InChIKey: 458402 (as provided)
• Storage conditions: Room temperature

Computed/literature identifiers (for reference; not item-specific specs)

• Preferred structural class: Linear aliphatic keto-ester (medium-chain, C14 backbone including two carbonyls)
• Suggested molecular formula (literature): C14H26O3
• Suggested molecular weight (literature): ~242.36 g/mol
• Example SMILES (literature): CCOC(=O)CCCCCC(=O)CCCC

Structural features (general chemistry description)

• Functional groups: One terminal ethyl ester (–COOEt) and one internal ketone (–CO–) at the ω-5/ω-6 region of a dodecyl chain (ketone nominally at C7 counting from the carboxyl carbon).
• 2D description: An ethyl ester carbonyl connected to a flexible methylene chain that contains a single internal ketone; the chain terminates in a saturated alkyl tail (no rings, no unsaturation, no heteroatoms beyond the three oxygens of ester and ketone).
• Stereochemistry: None (achiral, fully saturated linear chain).
• Polarity pattern: Amphiphilic; polar carbonyls at one end/middle and a long hydrophobic segment facilitating phase partitioning and surfactant-like behavior in certain systems.

Synthetic Utility

Key reactivity stems from the coexistence of an internal ketone and a terminal ethyl ester:

• Differential chemoselectivity:
  • Reduce ketone selectively (NaBH4, catalytic hydrogenation) to give secondary alcohol while retaining the ester; or reduce the ester (DIBAL-H, LiAlH4) to unveil alcohols while preserving/controlling ketone state.
• Enolate-based elaboration:
  • Form ketone enolates (LDA/LiHMDS) for aldol, Claisen–Schmidt, or alkylation reactions. The ester can be left intact to serve as a latent carboxyl function.
• Acyl transfer/Claisen chemistry:
  • Although the ester α-protons are more acidic, the internal ketone provides the more reactive enolate under strong base. Mixed Claisen condensations can be designed after appropriate protection or stepwise control.
• Carbon–carbon bond formation:
  • Wittig/HWE/Julia olefinations at the ketone to embed internal alkenes in the C12 chain.
  • Radical or nickel-catalyzed cross-couplings after converting the ester to redox-active esters (e.g., NHPI esters) to append fragments at the carboxyl terminus.
• Cyclizations and lactones:
  • Strategic oxidation/reduction followed by intramolecular esterification can generate medium-ring lactones of interest in flavor, fragrance, or materials research (research use only).

Overall, the scaffold is a versatile linchpin for building amphiphilic molecules, surfactant-like entities, and lipid-inspired architectures.

Target Specificity

Not applicable. This product is a small-molecule building block and is not an antibody, enzyme, or affinity reagent. No target, epitope, clone, or species reactivity is associated with this item.