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
carboxylic ester - aldehyde
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.
Certificados (CoA, COO, BSE/TSE y tabla de análisis)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Propiedades químicas y físicas
Peso molecular
130.139 g/mol
XLogP3
-0.100
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
5
Exact Mass
130.063 Da
Monoisotopic Mass
130.063 Da
Topological Polar Surface Area
43.400 Ų
Heavy Atom Count
9
Formal Charge
0
Complexity
98.500
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
Calculadoras de soluciones
Molarity Calculator
Determine the necessary mass, volume, or concentration for preparing a solution.
Dilution Calculator
Determine the dilution needed to prepare a stock solution.
Reconstitution Calculator
Reseñas
Reseñas de cliente
Application Protocols
Not applicable. No immunoassay or cell‑based application protocols (WB, IHC, IF, FC, etc.) are associated with this small‑molecule reagent. For synthetic and analytical procedures involving Ethyl 4‑oxobutanoate, refer to the Reaction & Applications and Reaction Conditions sections.
Biological Roles
This product is a small‑molecule chemical building block for research use and is not intended for biological administration.
General biochemical context (literature)
The 4‑oxobutanoate motif (succinic semialdehyde) appears in GABA catabolism (GABA transaminase produces succinic semialdehyde, which is then oxidized to succinate). The ethyl ester in Ethyl 4‑oxobutanoate is a synthetic derivative and not a known endogenous metabolite.
In vitro, the aldehyde group can form reversible adducts with amino residues (Schiff bases) in proteins and amines; such reactivity is exploited in derivatization chemistry but is not a biological function.
Practical note
For biochemical experiments (e.g., derivatization of amines), perform appropriate controls to account for aldehyde reactivity and potential hydrolysis of the ester in aqueous buffers. No claims are made regarding biological activity or safety in vivo.
Buffer Applications
This item is not a buffering reagent. Aldehyde–esters are generally unsuitable for preparing pH buffers and can undergo hydrolysis or adduct formation in aqueous media.
If used in aqueous experiments (e.g., derivatization assays), keep exposure to water minimal, work at low temperature, and use compatible buffers (avoid strong acids/bases and primary amine buffers that will react with aldehydes).
Green Alternatives
As a functional building block, Ethyl 4-oxobutanoate itself is not readily “replaced” by a greener solvent; however, greener choices can be made in its synthesis and use.
Greener solvents for reactions involving this reagent:
Replace DCM with EtOAc or 2‑MeTHF for many nucleophilic additions/condensations when compatible with reagents.
Use 2‑MeTHF or CPME in place of THF/Et2O for Grignard reactions (improved safety, lower peroxide tendency), verifying reactivity equivalence.
Use MeCN or EtOAc as alternatives to DMF/DMSO where feasible to reduce worker exposure concerns.
Process intensification and waste minimization:
Perform acetalizations with catalytic solid acids (e.g., Amberlyst) and azeotropic water removal to enable solvent recycling.
Employ flow addition for exothermic nucleophile additions to reduce solvent volumes and improve heat transfer.
Sourcing and synthesis considerations (literature):
Oxidation of ethyl 4‑hydroxybutanoate with green oxidants (e.g., O2/TEMPO or electrochemical methods) can afford Ethyl 4‑oxobutanoate, reducing heavy‑metal oxidant waste.
Biocatalytic routes from 1,4‑butanediol via alcohol oxidases and lipase‑mediated esterification may offer lower E‑factors, pending scale and availability.
Tradeoffs
Ether solvents like 2‑MeTHF are greener than THF in production and safety, but can change selectivity and require validation. EtOAc offers better environmental profile than chlorinated solvents but may co‑participate in transesterification under strong base/acid.
Pharmaceutical Uses
No pharmacopeial/excipient grade is specified for this item; refer to CoA/Spec Sheet. Content below addresses general formulation roles only and does not imply suitability for human use.
Potential formulation role (general): Reactive intermediate for synthesis of γ‑amino esters, lactams, and other building blocks that may be used upstream in pharmaceutical ingredient synthesis.
Not typically used as an excipient due to aldehyde reactivity, which can degrade actives (e.g., amines) or packaging components.
Handling in GMP contexts: If employed as a starting material or intermediate, control specifications often include identification by GC/IR, assay by GC, limits on acid content (from oxidation), residual solvents, and water by Karl Fischer. Storage under inert atmosphere and light protection is common practice to ensure consistency.
Physical Properties
Item-specific specifications were not provided. The following are general/literature/computed notes for the structure CCOC(=O)CCC=O; do not treat as product specifications.
Physical state/appearance (literature expectation): colorless to pale yellow liquid; characteristic aldehydic odor.
Boiling point: Not specified for this item; refer to CoA/Spec Sheet.
Melting point: Not specified for this item; refer to CoA/Spec Sheet.
Density: Not specified for this item; refer to CoA/Spec Sheet.
Refractive index: Not specified for this item; refer to CoA/Spec Sheet.
Solubility (general):
Miscible with many organic solvents (e.g., ethers, esters, chlorinated solvents, aromatics).
Limited stability in aqueous media due to hydrate formation at the aldehyde and slow ester hydrolysis under acidic/basic conditions; use minimal water exposure.
Vapor pressure/volatility: Moderate for an aldehyde–ester; handle in a fume hood to minimize inhalation of vapors.
Partitioning: Expect moderate hydrophobicity relative to simple esters; exact logP not specified for this item; refer to CoA/Spec Sheet.
pKa: No ionizable groups in neutral range; aldehyde undergoes reversible hydrate formation in water (equilibrium constant solvent- and temperature-dependent; literature generality).
Quality and Grades
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/Inhibitors: Not specified for this item. For aldehydic esters, vendors sometimes add trace acid or store under inert gas to suppress polymerization/oxidation; check the CoA if such measures are employed.
Interpretation and implications (general guidance)
Aldehyde content and acid number can drift upon storage due to oxidation or hydration; high‑purity material typically specifies acid value/GC area% on the CoA. If your application is base‑sensitive (e.g., enantioselective organocatalysis), verify residual acidity and water content by KF.
Chromatography/analytical use: For trace-level analytical work, confirm UV cut‑off and baseline behavior; low-UV “HPLC grade” is sometimes relevant for solvents, but for reagents like this, GC purity and specific impurities (e.g., 4‑oxobutanoic acid, diethyl succinate) are more critical.
Batch-to-batch consistency: Review CoA for GC assay, residual solvents, and stabilizer content to ensure reproducibility in condensation/addition chemistry.
Reaction and Applications
Ethyl 4-oxobutanoate is a versatile C4 synthon bearing an aldehyde and an ester, enabling orthogonal transformations and convergent assembly.
Reductive amination: Rapid formation of γ‑amino esters using primary/secondary amines followed by NaBH3CN, NaBH(OAc)3, or catalytic hydrogenation. Subsequent N‑acylation or cyclization gives lactams/piperidones.
Wittig/Horner–Wadsworth–Emmons olefination: Generation of α,β‑unsaturated esters (E/Z control via reagent choice and conditions). Useful in installing terminal vinyl esters that can undergo further cross‑coupling or conjugate additions.
Aldol/Knoevenagel condensations: Coupling with active methylene partners or enolizable carbonyls to access extended carbonyl frameworks; intramolecular variants furnish cyclic enones/lactones.
Acetalization/protection: Formation of dimethyl/diethyl acetals to mask the aldehyde during transformations at the ester (hydrolysis, reduction to alcohol, amidation), then deprotect under mild acid.
Nucleophilic additions: Grignard/organolithium reagents add at the aldehyde giving γ‑hydroxy esters; control via temperature and slow addition to avoid ester cleavage/transesterification.
Cyclizations: Conversion to 5‑membered heterocycles (e.g., via oxime formation then Beckmann rearrangement, or via intramolecular Michael/aldol strategies) and δ‑lactones after selective oxidation of the γ‑alcohol intermediate.
Practical tips
Separate the aldehyde chemistry from ester manipulations by temporary protection (acetal) or by chemoselective reductants (e.g., DIBAL for aldehyde vs LiAlH4 for global reduction).
Suppress self‑condensation with base scavengers, low temperature, and dilute conditions; use freshly opened reagent or verify purity by GC prior to sensitive reactions.
Reaction Conditions
General, literature‑based guidance for common transformations of Ethyl 4‑oxobutanoate; optimize for your system.
Reductive amination:
Conditions: Amine (1.2–1.5 equiv), AcOH (0.2 equiv) in MeOH, iPrOH, or MeCN; NaBH3CN (1.2–1.5 equiv) at 0–25 °C, 2–16 h.
Notes: Add reductant portionwise; employ molecular sieves or slow addition to manage water. Workup with bicarbonate to quench acid.
Wittig/HWE olefination:
Conditions: Ph3P=CHR or (EtO)2POCH2R (1.2–1.5 equiv) with base (NaH, t‑BuOK) in THF/DMF at 0–25 °C.
Notes: Mask the aldehyde as acetal if enolate chemistry at the ester is planned; otherwise, direct reaction is typically chemoselective for the aldehyde.
Nucleophilic additions (Grignard):
Conditions: RMgX (1.1–1.5 equiv) in anhydrous THF/Et2O at −78 to 0 °C, 0.5–3 h.
Notes: Prefer low temperature and slow addition to avoid over‑addition or transesterification; quench with saturated NH4Cl.
Acetalization:
Conditions: ROH (excess), catalytic p‑TsOH or camphorsulfonic acid, 3 Å sieves or Dean–Stark in toluene; 25–80 °C.
Notes: Monitor by NMR/GC; neutralize and remove acid thoroughly before base‑sensitive steps.
Workup/purification:
Avoid prolonged contact with strong base/silica; neutral silica or rapid flash chromatography recommended. For sensitive intermediates, distillation under reduced pressure or bulb‑to‑bulb may be preferable.
These conditions are general literature practices; actual yields and times will depend on substrates and scale.
Safety and Handling
Authoritative safety data are provided in the SDS; the following are general precautions for aldehyde–esters.
GHS classification, signal word, pictograms, and H‑statements: Not specified for this item; refer to SDS.
Likely hazards (general): Irritation to eyes/skin/respiratory tract; aldehydes can be sensitizers and strong lacrimators. Vapor may form flammable mixtures with air depending on temperature.
PPE: Use chemical-resistant gloves (e.g., nitrile), safety goggles/face shield, lab coat. Employ in a functioning fume hood.
Handling: Minimize exposure to moisture and bases/acids that can catalyze self‑condensation or hydrolysis. Keep containers tightly closed to limit oxidation of the aldehyde to the corresponding acid and to prevent peroxide formation in co‑stored ethers.
Inhalation: Move to fresh air; seek medical attention if symptoms persist.
Skin contact: Wash with plenty of water/soap; remove contaminated clothing.
Eye contact: Rinse cautiously with water for several minutes; remove contact lenses if present and easy; seek medical advice.
Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
Spills/Leaks: Absorb with inert material (vermiculite, sand). Avoid ignition sources. Ventilate area.
Waste: Dispose according to local regulations; segregate aldehyde‑containing organic waste.
Storage condition per product data: Room temperature. Protect from moisture and light; keep container tightly sealed.
Solvent Selection
This item is a reactive liquid building block rather than a routine process solvent. Solvent choice should optimize its carbonyl reactivity while controlling side reactions.
Polarity/miscibility: Readily soluble in common organic solvents (ethers such as THF/MTBE; esters such as EtOAc; aromatics such as toluene; chlorinated solvents such as DCM). Limited water compatibility due to aldehyde hydration and ester hydrolysis.
Selecting by transformation:
Nucleophilic additions (e.g., cyanation, Grignard): Use anhydrous ethereal solvents (THF, Et2O) at low temperature to moderate exotherms and suppress self‑condensation.
Condensations (Knoevenagel, aldol): Polar aprotic media (MeCN, DMF, DMSO) facilitate rate; include base and water scavenging.
Reductive amination: Alcoholic solvents (MeOH, iPrOH) or MeCN with molecular sieves to trap water; choose according to reductant compatibility (NaBH3CN, H2/Raney Ni, or borohydrides).
Acetal formation/protection: Use alcohol solvent (MeOH, EtOH) with catalytic acid and Dean–Stark or molecular sieves.
Comparison notes (general):
Versus saturated ethyl butyrate, the added aldehyde makes this compound more polar/reactive; avoid protic strong acids/bases unless intended.
Versus ketone analogs, aldehydes react faster with nucleophiles; employ lower temperatures and controlled addition to limit over‑reaction.
Drying: If needed, co‑evaporate with toluene and store over 3 Å sieves under inert gas to minimize hydrate formation.
Container: Store tightly closed in an amber glass bottle to limit light‑induced reactions; consider inert gas blanket (N2/Ar) to minimize oxidation of the aldehyde.
Moisture sensitivity: Aldehyde hydration and slow ester hydrolysis can occur; keep dry. For long‑term storage, keeping over activated 3 Å molecular sieves is beneficial.
Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
Preparation for use:
If the material has been stored for extended periods, verify identity/purity by GC or 1H NMR (check aldehyde proton ~9–10 ppm). If hydrate formation is suspected, gentle drying over sieves or co‑evaporation with toluene under reduced pressure can restore anhydrous state.
If chemoselectivity is critical, consider forming the acetal immediately after opening to protect the aldehyde during subsequent manipulations.
Freeze–thaw: Not generally applicable; avoid freezing aqueous mixtures. The neat reagent can be stored at ambient temperature; refrigeration may increase viscosity but can extend shelf life.
Research use note: For research use only.
Structure and Identity
Ethyl 4-oxobutanoate is a bifunctional aldehyde–ester building block (ethyl ester of 4‑oxobutanoic acid; also described as ethyl succinaldehydate).
InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
SMILES (literature): CCOC(=O)CCC=O
Structural features (general description)
Functional groups: one ethyl ester (–CO2Et) and one terminal aldehyde (–CHO) separated by a three‑carbon tether (γ‑oxo ester).
Skeleton: a four‑carbon chain bearing a carboxylate at C1 (as ethyl ester) and an aldehyde at C4 (ω‑aldehyde); no stereocenters.
Reactivity handles: electrophilic aldehyde (amenable to nucleophilic additions/condensations) and activated methylene α to the ester (enolate chemistry under strong base).
Synthetic Utility
Functional‑group complementarity makes Ethyl 4‑oxobutanoate a valuable synthon for C–C and C–N bond construction.
Key transformations (literature/general)
Chemoselective reductions: Aldehyde to alcohol (NaBH4, DIBAL) leaving ester intact; global reduction to 1,4‑butanediol or γ‑hydroxybutyl alcohols with LiAlH4 or catalytic hydrogenation under forcing conditions.
Reductive amination: Access to γ‑amino esters, precursors to pyrrolidines/piperidones via cyclization or to amides via coupling.
Olefination: Wittig/HWE delivers α,β‑unsaturated ethyl esters; subsequent Michael additions or epoxidations expand diversity.
Enolate chemistry at the ester α‑position: With strong base (LDA, NaHMDS), perform alkylation or aldol additions while masking the aldehyde as an acetal to avoid cross‑reactivity.
Cyclizations: After constructing a γ‑hydroxy ester, lactonization yields δ‑lactones under acidic conditions; or convert to oximes/hydrazones for further rearrangements.
Oxidations: Selective oxidation of the aldehyde to the corresponding acid affords ethyl succinate derivatives after workup; Baeyer–Villiger on related ketones gives access to lactones (not directly applicable to aldehydes).
Retrosynthetic value
Serves as a masked 1,4‑bifunctional handle enabling disconnections to amines, alkenes, or alcohols at C4 while preserving an ester at C1 for subsequent diversification (amidation, reduction, cross‑coupling via enolate chemistry).
Target Specificity
Not applicable. This product is a small‑molecule chemical reagent, not a biological targeting agent or antibody. No antigen/epitope specificity, clone, isotype, or species reactivity is associated with this item.
We use cookies to ensure the website functions properly and, where permitted, to improve your experience. You can manage your preferences at any time in Settings. Learn more in our Cookie Policy.
Shall we send you a message when we have discounts available?
Remind me later
Thank you! Please check your email inbox to confirm.
Products are supplied to verified businesses, institutions, and qualified professionals for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
