Ethyl 7-oxodecanoate , CAS No.73276-75-2

CAS: 73276-75-2 Cat. No.: E988856 Formula: C₁₂H₂₂O₃ Molecular Weight: 214.31 PubChem CID: 24727454

Storage

Room temperature

Specifications

Storage

Room temperature

Names and Identifiers

• Canonical Smiles: CCCC(=O)CCCCCC(=O)OCC
• IUPAC Name: ethyl 7-oxodecanoate
• InChIKey: KVJDBWMBTHGWQT-UHFFFAOYSA-N
• INCHI: 1S/C12H22O3/c1-3-8-11(13)9-6-5-7-10-12(14)15-4-2/h3-10H2,1-2H3
• Isomeric SMILES: CCCC(=O)CCCCCC(=O)OCC
• PubChem CID: 24727454
• Molecular Weight: 214.31

Taxonomic Classification

Taxonomy Tree

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

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: 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

Chemical and Physical Properties

• Molecular Weight: 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 validated bioassay or immunoassay protocols are associated with this small-molecule reagent in the product data.

General laboratory usage notes

• Preparation for reactions: Dry over molecular sieves (3Å/4Å) if water sensitivity is a concern. For precise stoichiometry, determine purity by GC or qNMR.
• Analytical methods: Monitor reactions by GC or LC-MS; the presence of two carbonyls affords clear IR signatures for conversion tracking.
• Solubility setup: For enzyme or biochemical tests, pre-dissolve in DMSO or ethanol to make a concentrated stock, then dilute into assay buffer keeping final organic cosolvent ≤ 1–5% v/v.

For any application-specific procedures, consult primary literature and validate conditions on small scale.

Biological Roles

Item-specific biological data are not provided for this SKU; the compound is supplied for research use only.

General context (literature)

• Structural class: medium-chain aliphatic keto-ester. While natural lipid metabolism involves fatty acids, acyl-CoAs, and β-oxo intermediates, ethyl esters with mid-chain ketones like Ethyl 7-oxodecanoate are typically synthetic analogs rather than established endogenous metabolites.
• Potential utility in biochemical research: May serve as a model substrate or probe in studies of ester hydrolysis (carboxylesterases) or carbonyl biotransformations (ketoreductases), where the spatial separation of ester and ketone can help dissect enzyme selectivity.
• Membrane interactions: Hydrophobic chain length suggests partitioning into lipid phases; however, specific partition coefficients, protein binding, or transport data for this exact structure are not established here.

Caveats

• No specific biological function, pathway involvement, or receptor interaction is assigned to this compound based on the product data provided.
• Any biological testing should be conducted under appropriate approvals; for research use only and not for diagnostic, therapeutic, or in vivo clinical applications.

Buffer Applications

This compound is a hydrophobic keto-ester and is not typically used to prepare aqueous buffers or to control pH in biochemical assays.

• Aqueous buffer systems (phosphate, Tris, HEPES, etc.) do not generally apply to this nonionic, water-insoluble substrate.
• For work involving this compound in aqueous media (e.g., enzyme assays), employ co-solvents (e.g., DMSO ≤ 1–5% v/v, or ethanol) to aid dissolution, ensuring cosolvent controls are included.

Refer instead to the sections on Solvent Selection, Reaction & Applications, and Synthetic Utility for relevant practical information.

Green Alternatives

Sustainability considerations for a medium-chain keto-ester primarily concern solvent and reagent choices rather than the substrate itself.

Greener processing choices (literature/general)

• Solvents: Prefer ethyl acetate, 2-MeTHF, CPME, or propylene carbonate over chlorinated solvents where feasible. Replace toluene/hexane with heptane or bio-based solvents when performance allows.
• Reductions: Use transfer hydrogenation (e.g., isopropanol with Ru- or Mn-based catalysts) or catalytic hydrogenation in ethanol over stoichiometric hydrides, minimizing inorganic waste.
• Oxidations: For Baeyer–Villiger-type steps, consider biocatalytic monooxygenases or H2O2/organocatalyst systems instead of peracids to reduce E-factors.
• Workup: Employ liquid–liquid extraction with greener solvents (EtOAc) and aqueous surfactant systems to reduce chlorinated waste.

Illustrative comparison (general)

• DCM vs EtOAc: DCM offers excellent dissolving power but comes with higher environmental and health concerns; EtOAc is biodegradable with lower toxicity, often sufficient for extractions/purifications.
• THF vs 2-MeTHF: 2-MeTHF (often bio-based) has lower miscibility with water, facilitating phase separations and reducing solvent usage; it also forms peroxides more slowly than THF, though monitoring is still needed.

Trade-offs

• Greener solvents can alter chemoselectivity (e.g., reductions) and rates. Validate on small scale, paying attention to phase behavior and catalyst compatibility.

Note: No item-specific green certifications or solvent restrictions are provided for this SKU.

Pharmaceutical Uses

No pharmacopeial grade, excipient status, or formulation role is specified for this item; refer to the CoA/Spec Sheet if required.

General context (non-clinical; research/manufacturing only)

• Medium-chain aliphatic esters are occasionally used as flavor/fragrance components or as process intermediates in the synthesis of API building blocks. A mid-chain ketone provides additional handles for selective derivatization in route scouting.
• As a hydrophobic liquid, such esters can sometimes act as solvents or plasticizers in research settings, but there is no indication that Ethyl 7-oxodecanoate is validated for such uses here.

Compliance note

• For research use only. Not indicated for human or veterinary drug products, parenteral administration, or clinical diagnostics without further qualification and regulatory review.
• If considering use in GMP contexts, establish impurity profiles, residual solvent limits, and stability-indicating methods according to ICH guidelines; item-specific data are not provided here.

Physical Properties

Item-specific specifications

• 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 (general guidance; not item specifications)

• Approximate molecular formula: C12H22O3 (keto-ester with a C10 backbone and ethyl ester terminus)
• Approximate molecular weight: ~214.30 g/mol
• Physical state: typically an oily liquid for medium-chain esters of this size (literature expectation)
• Polarity: moderately low; contains two carbonyls but overall hydrophobic alkyl chain dominates.
• Solubility: expected to be miscible with common organic solvents (e.g., dichloromethane, ethyl acetate, THF, toluene) and poorly soluble in water (literature expectation for C12 aliphatic esters).
• Volatility: significantly lower than short-chain esters; relatively high boiling point and low vapor pressure compared with C2–C6 esters (literature trend).

Not provided for this specific item (consult CoA/SDS or primary literature if needed)

• Boiling point, melting point
• Density, refractive index
• LogP, pKa, dielectric constant
• UV-Vis cutoff or extinction

Note: Use the product’s CoA/Spec Sheet for any method-critical parameters (e.g., refractive index for purity checks or residual solvent analyses).

Quality & Grades

Item-specific quality information

• 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 for interpreting grades (general)

• Research grade: Suitable for most synthetic, analytical, and method-development work. If GC/LC detection limits or UV transparency are critical, select a grade specified for those uses (e.g., HPLC/GC grade) with documented low background and tight contaminant controls.
• HPLC/GC grade (if applicable): Typically indicates low UV absorbance and low nonvolatile residue. For trace analysis, verify metals, water content, and residual solvent levels on the CoA.
• Purity reporting: For functionalized esters and ketones, purity by GC or HPLC is common. When chemoselectivity matters (e.g., reductions targeting only the ketone), minor impurities such as aldehydes, alcohols, or transesterification byproducts may impact outcomes.

What to verify on receipt (best practices)

• Identity confirmation by GC-MS or 1H/13C NMR (characteristic ester and ketone carbonyl resonances typically around 173–175 ppm and 205–215 ppm in 13C, literature ranges).
• Residual solvent and water levels if your application is moisture sensitive (Karl Fischer, GC headspace) — Not specified for this item; refer to CoA/Spec Sheet.
• Peroxide content is generally not a concern for aliphatic esters; routine peroxide testing is not typically required (unlike ethers).

Reaction & Applications

As a bifunctional aliphatic building block, Ethyl 7-oxodecanoate offers orthogonal reactivity at the internal ketone and terminal ester.

Representative transformations (literature/general)

• Chemoselective reduction: NaBH4 reduces the ketone to a secondary alcohol while typically leaving the ester intact, affording ethyl 7-hydroxydecanate analogs. Luche reduction (NaBH4/CeCl3) can improve selectivity.
• Oxime/hydrazone/semicarbazone formation: Direct condensation at the ketone enables derivatization for characterization or further transformations (e.g., Beckmann-type pathways after oxime formation).
• Baeyer–Villiger oxidation: The internal ketone can undergo insertion to yield a longer-chain ester; migratory aptitude and sterics govern regioselectivity.
• Wittig/Julia–Kocienski olefination: Conversion of the ketone to an internal alkene without perturbing the ester allows modular access to unsaturated intermediates.
• Aldol-type chemistry: Enolization alpha to the ketone permits C–C bond formation; the distal ester can be retained as a latent functional handle for later hydrolysis or amidation.
• Selective ketone hydrogenation: Catalytic hydrogenation (Pd/C, Raney Ni) can provide the saturated secondary alcohol; careful conditions avoid ester hydrogenolysis.
• Further ester chemistry: Hydrolysis to the 7-oxodecanoic acid, or amidation after activation (e.g., EDCI/HOBt) yields amides bearing a mid-chain ketone.

Use cases

• Synthesis of pheromone and flavor/fragrance intermediates where chain length and mid-chain oxidation dictate activity (literature precedent for medium-chain oxo-esters).
• Materials and surfactant R&D: introduction of polarity within hydrophobic chains.

Note: No manufacturer application notes were provided for this SKU; the above are literature-based exemplars.

Reaction Conditions

The following are literature-style, general conditions for functional group–typical transformations on a mid-chain keto-ester. Optimize for your substrate and scale.

• Chemoselective ketone reduction: NaBH4 (1–2 equiv) in MeOH, EtOH, or THF/MeOH (0–25°C, 0.5–2 h) often reduces the ketone preferentially, leaving the ester intact. Work up with aqueous NH4Cl or dilute acid. Monitor for base-promoted transesterification in neat alcohols.
• Luche reduction: NaBH4 (1.2 equiv) with CeCl3·7H2O (1.5 equiv) in MeOH at 0–5°C enhances 1,2-selectivity at the ketone (0.5–1 h).
• Catalytic hydrogenation: 5–10 wt% Pd/C (5–10 mol% metal) in EtOAc or EtOH under 1–3 bar H2 at RT–40°C reduces the ketone to alcohol; avoid over-reduction by short reaction times and low temperature.
• Oxime formation: Hydroxylamine·HCl (1.2–1.5 equiv), pyridine or NaOAc base, EtOH or MeOH, reflux 1–3 h. Isolate oxime for characterization or further transformations.
• Baeyer–Villiger oxidation: mCPBA (1.2–1.5 equiv) in DCM at 0–25°C, 2–16 h. Alternatively, H2O2 (30%) with catalytic acids or enzymes for greener options. Check regioselectivity and manage peracid safety.
• Ester hydrolysis: NaOH or KOH (1–2 M aq) with THF/MeOH co-solvent, 0–25°C to reflux, 1–6 h to give the acid. Acidify to pH ~2 for isolation.
• Amide formation: EDCI (1.2 equiv), HOBt or HOAt, DIPEA in DCM/DMF, 0–25°C, 2–16 h after prior hydrolysis to the acid.

These conditions are general literature guidance and not item-specific specifications.

Safety & Handling

Item-specific hazard information

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

General safety guidance (literature/chemical class)

• Expected hazards: Aliphatic esters and ketones of this chain length are commonly low volatility, combustible liquids that can cause skin/eye irritation on contact and may be harmful if swallowed or inhaled at high concentrations.
• PPE: Use safety glasses or goggles, lab coat, and appropriate chemical-resistant gloves (e.g., nitrile). Employ local exhaust ventilation or work in a fume hood to avoid inhalation of aerosols or mists.
• Handling: Avoid contact with strong oxidizers. Prevent moisture ingress if hydrolysis of the ester is a concern in your application. Limit exposure to strong bases and acids, which can promote transesterification, saponification, or hydration reactions at carbonyls.
• Storage incompatibilities: Separate from strong oxidizing agents, strong acids/bases, and reducing agents. Avoid prolonged exposure to light and elevated temperatures to minimize degradation.
• First aid overview: If on skin/eye, rinse with plenty of water for at least 15 minutes; remove contaminated clothing. If inhaled, move to fresh air. If ingested, rinse mouth; do not induce vomiting; seek medical attention. Always follow SDS instructions.
• Spill/cleanup: Absorb with inert material (e.g., vermiculite), collect in suitable container for disposal. Eliminate ignition sources.

Authoritative data source: Always defer to the product’s SDS for definitive hazard classification, exposure limits, and emergency measures.

Solvent Selection

Chemical class context

• Ethyl 7-oxodecanoate is a hydrophobic, medium-chain aliphatic keto-ester. It dissolves readily in many organic solvents and poorly in water (literature expectation for C12 esters).

Selection guidance (general)

• Polar aprotic solvents (e.g., dichloromethane, THF, acetonitrile): Good for reactions at the ketone (oxime/hydrazone formation, NaBH4 reductions) and for many catalytic oxidations or hydrogenations.
• Moderately polar esters/ethers (ethyl acetate, MTBE, CPME, 2-MeTHF): Often excellent for workups, extractions, and greener processing. Ethyl acetate commonly provides good solubility and easy removal.
• Nonpolar solvents (toluene, heptane): Useful when minimizing polarity is advantageous (e.g., selective reductions, phase-separable workups) or for high-temperature operations.
• Alcohols (MeOH, EtOH, iPrOH): May participate in transesterification under acidic/basic conditions; avoid if ester exchange is undesirable.

Miscibility profile (literature trends)

• Water: expected to be sparingly soluble/insoluble.
• Organic: high solubility in halogenated solvents, aromatic hydrocarbons, ethers, and esters.

Practical tips

• For NaBH4 chemoselective reduction of the ketone in the presence of the ester, protic alcohol co-solvents can accelerate; consider MeOH/THF mixtures while monitoring for any ester cleavage under basic conditions.
• For chromatographic purification, hexanes/ethyl acetate gradients typically provide good separation for this polarity range.
• If odor carryover or flavor cross-contamination is a concern, avoid recycling glassware from fragrance work without stringent cleaning; medium-chain esters can be persistent.

Storage & Reconstitution

Item-specific storage

• Storage Conditions (product data): Room temperature.
• Shipped In: Not specified for this item; refer to CoA/Spec Sheet.

General handling and stability (literature/typical for aliphatic keto-esters)

• Container: Store in a tightly sealed, chemically compatible container (amber glass recommended) to minimize light exposure and oxidative degradation.
• Atmosphere: For long-term storage, consider an inert gas blanket (nitrogen/argon), especially if repeated opening is expected.
• Moisture: While esters are relatively stable, prolonged exposure to moisture and basic conditions can lead to hydrolysis; keep dry for best shelf life.
• Temperature: Ambient storage is generally acceptable per product data; avoid heat sources. Refrigeration can further extend shelf life if crystallization is not an issue (typically a liquid).

Reconstitution

• Supplied neat; no reconstitution is required. If preparing solutions, use dry, oxygen-poor solvents when sensitivity is a concern. Record concentration, solvent, and date on container; for long-term stock solutions, store at 2–8°C and protect from light.

Always refer to the product’s CoA and SDS for definitive guidance on storage constraints and stability-indicating conditions.

Structure & Identity

Ethyl 7-oxodecanoate is a linear aliphatic keto-ester featuring a medium-chain backbone with a terminal ethyl ester and an internal ketone functionality.

• SKU: E988856
• Product Name: Ethyl 7-oxodecanoate
• CAS: 73276-75-2 (product data)
• PubChem CID: 24727454 (product data)
• InChIKey: 190597 (product data)
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.

Item-specific (from Product Data)

• Storage Conditions: Room temperature
• Category Path: 全部 / 可售 / 生命科学
• Research Use Note: For research use only

Structural features (general description)

• Functional groups: one secondary ketone (internal) and one ethyl ester (terminal). No heteroatoms besides the three oxygens in the carbonyl groups.
• Carbon skeleton: unbranched C10 fatty chain framework; the ketone is located at C7 relative to the carboxyl carbon (literature understanding of “7-oxo”).
• Stereochemistry: none (achiral as drawn; no stereogenic centers).
• 2D description in words: An ethyl ester headgroup (–COOCH2CH3) attached to a straight alkyl chain bearing an internal ketone; overall a bifunctional, nonconjugated keto–ester separated by multiple methylenes.

Computed/literature identifiers (for reference; not item specifications)

• Typical molecular formula (literature): C12H22O3
• Typical molecular weight (literature): ~214.30 g/mol

Note: Exact identifiers (SMILES/InChI) and any stereochemical or positional isomer specifics for this catalog item should be confirmed against the CoA/Spec Sheet.

Synthetic Utility

Functional handle synergy

• Internal ketone: amenable to nucleophilic additions, reductive transformations, oxime/hydrazone formation, and oxidative rearrangements (e.g., Baeyer–Villiger). The ketone’s α-positions enable enol/enolate chemistry for C–C bond formation.
• Terminal ethyl ester: robust under many conditions; can be saponified to the acid, reduced to the alcohol (LiAlH4, BH3) or aldehyde (DIBAL-H, controlled), or converted to amides via coupling (EDC/HATU).

Strategic value (literature/general)

• Orthogonality: Selective reduction of the ketone (NaBH4) generates a secondary alcohol while preserving the ester, enabling late-stage diversification (e.g., ester-to-amide switch).
• Chain editing: Through aldol or Michael-type extensions at the ketone α-carbon, followed by ester manipulations, one can access a range of ω-functionalized acids/esters.
• Masked functionality: The ethyl ester acts as a protecting/activating group for the carboxylate; hydrolysis restores the acid for further coupling (e.g., to form surfactant-like amides with tailored HLB).
• Pheromone/flavor intermediates: Mid-chain oxidation patterns are frequent motifs; the present scaffold expedites access to both reduced (alcohol) and oxidized (lactone/ester via Baeyer–Villiger) derivatives.

Analytical cues

• 13C NMR typically shows distinct carbonyl resonances for ester (~173–175 ppm) and ketone (~205–215 ppm). IR exhibits two strong C=O bands (ester ~1735–1750 cm−1; ketone ~1705–1720 cm−1), aiding identity confirmation (literature ranges).

Target Specificity

Not applicable. This product is a small-molecule keto-ester, not a biological targeting reagent (e.g., antibody, ligand with defined target profile). No antigen, epitope, species reactivity, clone, or isotype information is relevant.