4-OXOHEXANOIC ACID - ≥97% , CAS No.1117-74-4

CAS: 1117-74-4 Cat. No.: O165944 Formula: C₆H₁₀O₃ Peso molecolare: 130.145 Numero EC: 620-812-4

GRADE & PURITY ≥97%

Synonyms

4-keto-n-caproic acid | LMFA01060009 | AMY30226 | 4-oxohexanoicacid | AS-57457 | Hexanoic acid, 4-oxo- | 4-oxohexanoic acid | 4-oxo-hexanoic acid | DTXSID20912252 | EN300-149328 | AKOS003382263 | Q63392356 | SY270773 | CLJBDOUIEHLLEN-UHFFFAOYSA-N | Z83895

Storage

Store at 2-8°C

Shipped In

Wet ice

Specifications

Sinonimi

4-keto-n-caproic acid | LMFA01060009 | AMY30226 | 4-oxohexanoicacid | AS-57457 | Hexanoic acid, 4-oxo- | 4-oxohexanoic acid | 4-oxo-hexanoic acid | DTXSID20912252 | EN300-149328 | AKOS003382263 | Q63392356 | SY270773 | CLJBDOUIEHLLEN-UHFFFAOYSA-N | Z83895

Specifiche e purezza

≥97%

Condizioni di conservazione di stoccaggio

Store at 2-8°C

Spedito in

Wet ice

Questo prodotto richiede spedizione a catena fredda. I servizi di terra e altri servizi economici non sono disponibili.

Purezza

≥97%

Nomi e identificatori

• Pubchem Sid: 504762736
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504762736
• Sorrisi canonici: CCC(=O)CCC(=O)O
• IUPAC Name: 4-oxohexanoic acid
• InChIKey: CLJBDOUIEHLLEN-UHFFFAOYSA-N
• INCHI: 1S/C6H10O3/c1-2-5(7)3-4-6(8)9/h2-4H2,1H3,(H,8,9)
• Isomeri SMILES: CCC(=O)CCC(=O)O
• Peso molecolare: 130.145
• Reaxy-Rn: 1755111
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1755111&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Classe Keto acids and derivatives
      • Subclass Medium-chain keto acids and derivatives

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Classe: Keto acids and derivatives
• Subclass: Medium-chain keto acids and derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Medium-chain keto acids and derivatives
• Alternative Parents: Gamma-keto acids and derivatives Ketones Monocarboxylic acids and derivatives Carboxylic acids Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Medium-chain keto acid - Gamma-keto acid - Ketone - Monocarboxylic acid or derivatives - Carboxylic acid - 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 medium-chain keto acids and derivatives. These are keto acids with a 6 to 12 carbon atoms long side chain.
• External Descriptors: Oxo fatty acids

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: 130.139 g/mol
• XLogP3: 0.000
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 130.063 Da
• Monoisotopic Mass: 130.063 Da
• Topological Polar Surface Area: 54.400 Ų
• Heavy Atom Count: 9
• Formal Charge: 0
• Complexity: 117.000
• 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 application protocols are provided for this small-molecule reagent in the Product Data. Typical uses are synthetic and method-development oriented. For guidance, see the Reaction Conditions and Synthetic Utility sections, and tailor conditions to your specific transformation and analytical methods.

Biological Roles

This compound is a synthetic small-molecule γ‑keto acid and is not known as a primary metabolite or cofactor in central biochemical pathways.

• General biochemical considerations (literature)

  • Carboxylic acids with adjacent carbonyls can interact with enzymes that recognize short-chain acids or carbonyls, but 4‑oxohexanoic acid is not a canonical metabolite.
  • The ketone can form reversible imines with primary amines (e.g., lysine side chains) under certain conditions; such reactivity is primarily a chemical derivatization phenomenon rather than a defined biological role.

• Research context

  • May serve as a model substrate in studies of carbonyl chemistry (oxime/hydrazone formation) or as a handle for preparing labeled derivatives for analytical method development.

No biological activity or physiological function is claimed or implied; for research use only.

Buffer Applications

4‑Oxohexanoic acid is not typically employed as a biological buffer. Its pKa and reactivity (enolization and carbonyl condensations) make it unsuitable for maintaining stable pH in biochemical assays.

• If a buffering system is required, select established buffers (e.g., acetate, MES, MOPS, phosphate) appropriate to the target pH range.

Refer instead to the Synthetic Utility and Reaction & Applications sections for relevant uses of this compound.

Green Alternatives

• Solvent choices

  • Favor greener solvents (EtOAc, 2-MeTHF, CPME, alcohols) over DMF/NMP/DMSO when feasible. Many transformations of 4‑oxohexanoic acid (esterification, coupling with greener reagents, oxime formation) proceed in EtOAc, MeOH/EtOH, or 2‑MeTHF with proper optimization.

• Reagent selection

  • For amide couplings, consider EDC·HCl with catalytic DMAP in EtOAc or aqueous-organic media to minimize hazardous solvents, instead of HATU/HOAt systems.
  • For reductions, catalytic hydrogenation (H2/Pd or H2/Raney Ni in EtOH) can replace stoichiometric hydrides when chemoselectivity permits.

• Energy and workup

  • Utilize continuous removal of water (azeotropic or molecular sieves) to drive esterifications at lower acid catalyst loadings.
  • Apply solvent recycling and switch to distillable ethers/esters rather than high-boiling amides to simplify waste handling.

• Comparison snapshot (general)

  • DMF/NMP: excellent solubility/activation; regulatory scrutiny and difficult removal.
  • 2-MeTHF/EtOAc: renewable or biodegradable profiles, easier workup; sometimes lower solubility, may need slight heating or cosolvent.
  • Alcohol solvents: benign profile; can participate in reaction (esterification/transesterification) under acid catalysis—control conditions accordingly.

Pharmaceutical Uses

This product is offered for research and laboratory use only.

• General formulation context (no therapeutic claims)

  • 4‑Oxohexanoic acid can function as a synthetic intermediate for preparing more complex molecules (e.g., keto‑esters, keto‑amides) in medicinal chemistry workflows.
  • The free acid is not a typical excipient. If used in preclinical discovery, it is usually transformed (esterified, amidated, or otherwise derivatized) to tune physicochemical properties.

• Regulatory status

  • No pharmacopeial monograph is known for 4‑oxohexanoic acid. Any use in GMP contexts would require appropriate qualification and method validation.

For any development work, consult internal quality systems and risk assessments; this listing does not provide clinical or therapeutic guidance.

Physical Properties

• Item-specific (Product Data)

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

• Literature/computed values (reference only; not product specifications)

  • Molecular formula: C6H10O3; Molecular weight: 130.14 g/mol.
  • Acid–base: Carboxylic acid pKa typically ~4–5 for saturated aliphatic acids; the adjacent ketone may slightly influence acidity (literature, general trend).
  • Tautomerism: Exists predominantly as the keto form; minor enol content possible near the ketone (literature, general behavior of γ‑keto acids).
  • Solubility: Expected to be miscible with many polar organic solvents (MeOH, EtOH, acetone, acetonitrile) and to have moderate solubility in water due to the carboxyl group (literature expectation; verify experimentally for your system).
  • Partitioning: LogP anticipated in the low positive range for a C6 monoacid with a ketone (literature expectation for similar γ‑keto acids).
  • Boiling/Melting: Discrete boiling point may be obscured by thermal degradation; many keto‑acids show decomposition upon heating (literature generality). Determine by DSC/TGA if needed.
  • Refractive index/density: Not widely reported for this specific compound; measure as needed for process design.

Note: For authoritative, lot-specific values (water content, residual solvents, metals, UV cutoff), refer to the CoA/Spec Sheet for this SKU.

Quality and Grades

• Item-specific (Product Data)

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

• What grade implies (general guidance)

  • Research or synthesis grade keto–acids are typically controlled for identity (1H/13C NMR, IR), purity (GC/HPLC), and residual solvents. If designated “≥95%” or higher, minor related impurities often include self-condensation products or hydration/tautomer components.
  • Stabilizers: None indicated for this item. In the absence of stabilizers, store cool (2–8 °C) as provided and minimize headspace oxygen and heat to limit side reactions (e.g., aldol self-condensation under basic contamination).

• Documentation and release testing

  • Review the lot-specific CoA for: assay (% area by GC/HPLC), identity spectra, appearance, and any applicable limits (water, metals, residual solvents, aldehydes/ketones). If UV applications are intended, verify UV absorbance profile as it is not specified for this item.

• Practical note

  • If your application is moisture- or base-sensitive (e.g., enolate chemistry), consider in-house pre-drying and titration (Karl Fischer for water, acid value) to ensure reproducible performance.

Reaction and Applications

As a γ‑keto acid, 4-oxohexanoic acid is a versatile bifunctional building block combining carboxylic acid reactivity with an enolizable ketone.

• Carbonyl transformations

  • Oxime/hydrazone formation with hydroxylamine or hydrazines; useful for derivatization and intermediate stabilization. Reductive amination (NaBH3CN or H2/Pd after imine formation) provides β‑substituted amines once the ketone is converted.
  • Chemoselective reduction: NaBH4 or catalytic hydrogenation can reduce the ketone to the corresponding hydroxy acid, typically leaving the carboxyl group intact. Stronger hydride (e.g., BH3·THF) reduces the acid to the primary alcohol, if desired.

• Carboxyl-group manipulations

  • Esterification (Fischer, Steglich) to alkyl esters for subsequent Claisen or enolate chemistry.
  • Amide coupling (EDC/HOBt, HATU/HOAt, or CDI) to access keto-amides; judicious base to suppress self-condensation.

• Enolate/umpolung chemistry at C3 (α to the ketone)

  • LDA/LiHMDS in THF or toluene at −78 to 0 °C enables alkylation, aldol, or Michael additions. Protect or pre-esterify the acid to prevent base consumption and aggregation.

• Decarboxylation and rearrangements

  • While β‑keto acids decarboxylate readily, γ‑keto acids are more resistant; however, activation (e.g., conversion to β‑keto esters or acylation to mixed anhydrides) can enable thermolysis or Hunsdiecker-type variants.

• Synthesis applications (examples, literature)

  • Precursor to 1,4-diols via sequential ketone reduction and acid reduction.
  • Entry to heterocycles after carbonyl derivatization (oxime → Beckmann-type transformations) or via intramolecular aldol when the acid is converted to an aldehyde/ester.

Reaction Conditions

General literature guidance for common transformations of 4‑oxohexanoic acid (optimize for your system):

• Ketone to oxime/hydrazone

  • Solvent: EtOH or MeOH with 0.5–1.0 equiv AcOH as catalyst; or aqueous ethanol.
  • Reagents: Hydroxylamine·HCl (1.1–1.5 equiv) or hydrazine derivatives.
  • Temperature/time: RT to 60 °C, 1–6 h.

• Reductive amination at the ketone

  • Solvent: MeOH, EtOH, or THF.
  • Reagents: Primary amine (1.1–1.5 equiv), NaBH3CN (1.2–2.0 equiv) or H2/Pd.
  • Conditions: pH 5–6 (AcOH/AcONa), RT to 40 °C, 2–16 h.

• Chemoselective ketone reduction

  • Solvent: MeOH, EtOH, or i‑PrOH.
  • Reagent: NaBH4 (1.1–1.5 equiv) at 0 °C to RT for 0.5–2 h. Quench carefully.

• Esterification (Fischer)

  • Solvent/reagent: Neat alcohol (ROH) or ROH/toluene with catalytic H2SO4 or p‑TsOH (1–5 mol%).
  • Conditions: Reflux with water removal (Dean–Stark if needed), 2–12 h.

• Amide coupling

  • Solvent: DMF, DCM, or EtOAc (greener choice) with DIPEA or NMM base.
  • Reagents: EDC·HCl (1.1–1.5 equiv) + catalytic DMAP or HATU (1.1–1.2 equiv).
  • Temperature: 0 °C to RT, 1–16 h.

• Enolate formation/alkylation (at C3)

  • Solvent: Anhydrous THF or toluene.
  • Base: LDA or LiHMDS (1.1–1.5 equiv) at −78 to −20 °C.
  • Note: Protect the carboxyl as an ester or employ excess base to compensate acid quench; maintain rigorously dry, oxygen-free conditions.

Yields and selectivities depend on substituents, solvent, and temperature; confirm by small-scale optimization.

Safety and Handling

• Item-specific (Product Data)

  • Storage conditions: Store at 2–8 °C; ship on wet ice.
  • GHS signal word, hazard statements, pictograms: Not specified for this item; refer to SDS.

• General hazards of aliphatic keto–acids (literature/typical)

  • May cause skin and eye irritation and respiratory tract irritation if aerosols/vapors are generated.
  • Organic acids can be corrosive to some metals and may react with bases to form salts, releasing heat.

• Handling recommendations (good laboratory practice)

  • Use in a fume hood. Avoid inhalation of vapors/mists and contact with skin/eyes.
  • PPE: Lab coat, chemical-resistant gloves (e.g., nitrile), safety goggles/face shield.
  • Incompatibilities: Strong bases (exothermic neutralization), strong oxidizers, strong reducing agents, acid chlorides/anhydrides (if unintended acylation), and reactive metals.
  • Special considerations: Although peroxide formation is not a typical concern for this class, the ketone can undergo imine/oxime formation with amines/hydroxylamine—avoid unintended contact in storage areas.

• First-aid overview (consult SDS for details)

  • Skin/eye contact: Rinse cautiously with water for several minutes; remove contaminated clothing; seek medical attention for persistent irritation.
  • Inhalation: Move to fresh air; monitor breathing; seek medical attention if symptoms occur.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.

Always consult the product SDS for definitive hazard classification and emergency procedures.

Solvent Selection

4-Oxohexanoic acid combines a polar protic acid with a polar aprotic ketone, giving amphiphilic behavior.

• Polarity/miscibility (literature expectations)

  • Highly soluble in polar protic solvents: methanol, ethanol, isopropanol.
  • Highly soluble in polar aprotics: acetone, acetonitrile, DMF, DMSO, THF.
  • Water: anticipated moderate solubility due to carboxyl functionality; confirm experimentally for your concentration and temperature.
  • Limited solubility in nonpolar hydrocarbons (hexane, heptane); solubility improves in ether esters or with small amounts of polar cosolvent.

• Selection guidance by use case

  • Amide coupling: DMF, NMP, or DCM with coupling reagents (HATU/EDC) and organic bases (DIPEA). For greener choices, EtOAc or 2-MeTHF with soluble additives can work.
  • Esterification (Fischer): Anhydrous alcohol solvent (ROH) with catalytic acid; remove water azeotropically (Dean–Stark with toluene/xylenes as co-solvent) if needed.
  • Carbonyl derivatization (oxime/hydrazone): Aqueous alcohols or AcOH-containing media to promote condensation.
  • Enolate chemistry at the methylene α to the ketone: Use dry, aprotic solvents (THF, THF/hexanes, toluene) and strong bases (LDA, LiHMDS) at low temperature; strictly exclude moisture.

• Quick comparison (general)

  • DMSO/DMF: maximal solubility, but harder workup.
  • MeOH/EtOH: benign and easy removal; may transesterify or esterify under acidic conditions.
  • 2-MeTHF/EtOAc: greener alternatives with good handling; verify solubility at scale.

Storage and Reconstitution

• Item-specific (Product Data)

  • Storage: Store at 2–8 °C.
  • Shipping: Shipped on wet ice.

• Practical guidance

  • Keep container tightly closed under an inert headspace if possible to minimize oxidative or aldol-type side reactions during long storage.
  • Protect from strong bases and nucleophiles; avoid prolonged exposure to elevated temperatures.
  • If solid/oil separation or crystallization occurs on cold storage, gently warm to ambient and mix thoroughly before use. If necessary, prepare solutions freshly in dry, appropriate solvents (e.g., MeOH, EtOH, THF, EtOAc, or DMF) immediately prior to reaction.
  • For sensitive enolate chemistry, consider drying by azeotrope (toluene), storing over molecular sieves (for solutions), and titrating water content (KF) as needed.

• Stability notes

  • No stabilizer is specified for this item. For long-term storage, the recommended 2–8 °C conditions and minimal headspace are typically sufficient. Consult the CoA/SDS for any additional handling instructions specific to your lot.

Structure and Identity

Brief description: 4-Oxohexanoic acid is a linear aliphatic keto–acid containing a terminal carboxylic acid and an internal ketone functional group separated by a two‑carbon spacer.

• Item-specific (Product Data)

  • SKU: O165944
  • CAS: 1117-74-4
  • PubChem CID: 3799774
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
  • Research use: For research use only

• Literature/computed identity (for reference; not a specification)

  • Synonyms: 4-oxohexanoic acid; 4-ketohexanoic acid; γ-ketohexanoic acid
  • Molecular formula: C6H10O3 (literature)
  • Molecular weight: 130.14 g/mol (literature)
  • Canonical SMILES: O=C(O)CC(=O)CC (literature)
  • InChI (skeletal): InChI=1S/C6H10O3/c1-2-4-5(7)3-6(8)9/h2-4H2,1H3,(H,8,9) (literature)

• Structural features (descriptive)

  • One terminal carboxylic acid (–CO2H) and one internal ketone (–C(=O)–) at the 4-position relative to the acid carbonyl (γ‑keto acid).
  • Acyclic, no stereocenters; capable of keto–enol tautomerism at the methylene alpha to the ketone.
  • 2D layout in words: HOOC–CH2–CH2–C(=O)–CH2–CH3 (carboxyl carbon is C1; ketone carbonyl is C4).

Synthetic Utility

Key functional groups and reactivity that make 4‑oxohexanoic acid valuable in synthesis:

• Bifunctional handle

  • Carboxylic acid: amenable to esterification, amidation, and activation (acid chlorides/anhydrides via SOCl2, oxalyl chloride, or DCC/CDI coupling routes).
  • Ketone: supports enolate generation, aldol/Michael chemistry, oxime/hydrazone/imines, and selective reductions.

• Strategic uses

  • Build β‑substituted frameworks: Enolization at C3 (α to ketone) enables alkylation or aldol addition, followed by downstream manipulation of the acid.
  • Polarity inversion: Convert the acid to a Weinreb amide to access ketones or aldehydes distal to the original ketone after selective transformations.
  • Protect/react: Temporarily mask the acid as a methyl/benzyl ester to conduct strong-base chemistry without acid–base quenching; deprotect later (acidolysis or hydrogenolysis for Bn).

• Named/related transformations (literature)

  • Steglich esterification (DCC/DMAP) to form esters at mild temperature.
  • Reductive amination of the ketone to introduce nitrogen, then EDC/HATU coupling of the acid to assemble keto‑amides or amino alcohol derivatives.
  • Chemoselective hydride reduction: NaBH4 reduces the ketone to a secondary alcohol while leaving the acid intact; BH3·THF reduces the acid to primary alcohols.

This combination enables concise routes to β‑functionalized acids, keto‑amides/esters, and building blocks for heterocycles.

Target Specificity

Not applicable. This product is a small-molecule reagent, not a biological targeting reagent (e.g., antibody, ligand, or probe). No antigen, epitope, clone, or species reactivity is associated with this item.