5-Acetyloxolan-2-one - ≥95% , CAS No.29393-32-6

CAS: 29393-32-6 Cat. No.: A1068529 Fórmula: C₆H₈O₃ Peso molecular: 128.13 PubChem CID: 62856

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

Especificações e pureza

≥95%

Condições de armazenamento de armazenamento

Room temperature

Pureza

≥95%

Nomes e identificadores

• Sorrisos canónicos: CC(=O)C1CCC(=O)O1
• IUPAC Name: 5-acetyloxolan-2-one
• InChIKey: AHLDCEZSQNGEFT-UHFFFAOYSA-N
• INCHI: 1S/C6H8O3/c1-4(7)5-2-3-6(8)9-5/h5H,2-3H2,1H3
• SMILES isoméricas: CC(=O)C1CCC(=O)O1
• PubChem CID: 62856
• Peso molecular: 128.13

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Classe Organooxygen compounds
      • Subclass Carbonyl compounds
        • Level5 Alpha-acyloxy carbonyl compounds
          • Level6 Alpha-acyloxy ketones

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Classe: Organooxygen compounds
• Subclass: Carbonyl compounds
• Intermediate Tree Nodes: Alpha-acyloxy carbonyl compounds
• Direct Parent: Alpha-acyloxy ketones
• Alternative Parents: Gamma butyrolactones Tetrahydrofurans Ketones Carboxylic acid esters Oxacyclic compounds Monocarboxylic acids and derivatives Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aliphatic heteromonocyclic compounds
• Substituents: Alpha-acyloxy ketone - Gamma butyrolactone - Tetrahydrofuran - Lactone - Ketone - Carboxylic acid ester - Oxacycle - Organoheterocyclic compound - Monocarboxylic acid or derivatives - Carboxylic acid derivative - Organic oxide - Hydrocarbon derivative - Aliphatic heteromonocyclic compound
• Descrição: This compound belongs to the class of organic compounds known as alpha-acyloxy ketones. These are ketones that have an acyloxy substituent alpha to the carbonyl group. They have the general structure R4C(=O)OC(R2)(R3)C(R1)=O (R1=organyl, R4=H or organyl; R2,R3 = any atom).
• 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

Propriedades químicas e físicas

• Peso molecular: 128.130 g/mol
• XLogP3: 0.000
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 128.047 Da
• Monoisotopic Mass: 128.047 Da
• Topological Polar Surface Area: 43.400 Ų
• Heavy Atom Count: 9
• Formal Charge: 0
• Complexity: 150.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 1
• 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

Not applicable. There are no immunoassay or molecular biology application protocols (e.g., WB, IHC, IF, FC) associated with this small-molecule building block.

For chemical applications, see the Reaction Conditions and Synthetic Utility sections for general laboratory guidance on using 5‑acetyloxolan‑2‑one in synthesis.

Biological Roles

This compound is a synthetic small molecule (lactone/ketone) and is not known to have endogenous biological roles. It is primarily used as a chemical intermediate in research and synthesis. Any discussion of metabolism, signaling, or physiological activity would be speculative and is outside the scope of the Product Data.

General considerations (literature, non-clinical):

• Lactones can be substrates for hydrolytic enzymes (lactonases), yielding hydroxyacids; however, specific enzymatic pathways for 5‑acetyloxolan‑2‑one are not established in the literature to a degree suitable for generalization.
• In vitro studies may use this scaffold to explore structure–reactivity relationships of butenolide precursors, but such work concerns chemistry rather than biological function.

Note: For research use only (per Product Data). No medical, diagnostic, or therapeutic uses are intended.

Buffer Applications

Not typically applicable. 5-Acetyloxolan-2-one is not used as a buffering agent. It lacks acid–base pairs suitable for preparing defined pH buffer systems in aqueous media.

Practical tip: If your workflow involves this compound in aqueous phases (e.g., bioconjugation of ring‑opened derivatives), select an appropriate external buffer system (e.g., phosphate, acetate, HEPES) based on the reactivity of your other functional groups, and avoid extremes of pH that could induce unwanted lactone hydrolysis unless that transformation is desired.

Green Alternatives

Context: 5-Acetyloxolan-2-one is a functionalized building block rather than a process solvent. Greener choices relate to how you use it (solvents, reagents, and routes) and to potential bio‑based feedstocks.

Greener processing strategies (literature/general):

• Solvent choices: Prefer low-toxicity, biorenewable, or safer solvents when feasible (e.g., 2‑MeTHF over THF; ethyl acetate or Me‑tB ether instead of DCM/CHCl3; water/EtOH for ring‑opening reactions).
• Catalysis: Use organocatalysts (e.g., proline, piperidine) for aldol/Knoevenagel instead of stoichiometric strong bases where selectivity permits. Apply heterogeneous catalysts (e.g., acidic resins) for lactone openings to minimize waste.
• Energy: Conduct condensations under solvent‑free or mechanochemical conditions where possible; microwave assistance can shorten times and reduce energy use.
• Feedstocks: Consider routes from platform molecules such as levulinic acid or bio‑derived succinic acid followed by cyclization/acetylation, potentially lowering fossil‑based inputs.

Illustrative comparison for common operations (general):

• Aldol at acetyl group: 2‑MeTHF or CPME with LDA/NaHMDS (dry) vs THF/DCM — similar selectivity, reduced peroxide risk (2‑MeTHF still forms peroxides; manage accordingly), often easier workup.
• Ring opening to hydroxyesters: EtOH or MeOH as solvent/reagent with acidic ion‑exchange resin vs DCM with mineral acids — mitigates chlorinated waste and corrosion.

Trade‑offs: Some greener solvents alter rates/selectivities; ensure pilot studies and solvent‑swap risk assessment (bp, azeotropes, recyclability) before scale‑up.

Pharmaceutical Uses

No pharmacopeial/excipient status is provided for this item. This compound is primarily a research and synthetic intermediate and is not offered for clinical or diagnostic use.

General, non-clinical context:

• Role in drug discovery chemistry: The lactone–ketone motif can serve as a fragment or scaffold in medicinal chemistry campaigns, enabling rapid diversification via enolate chemistry, ring opening, and reductive transformations.
• Process considerations: If used as a starting material or intermediate, attention should be paid to impurity fate-and-purge studies (e.g., ring‑opened acids, aldol dimers) and to solvent selection aligned with ICH Q3C.

Important: No therapeutic claims are made or implied. For regulated applications, confirm compliance and suitability through your internal quality systems and the Aladdin CoA/Spec Sheet for SKU A1068529.

Physical Properties

Item-specific specifications (this product):

• 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.
• Boiling point, melting point, density, refractive index, solubility, UV cutoff, water/peroxide/metal limits: Not specified for this item; refer to CoA/Spec Sheet.

Literature/general reference (not item-specific):

• Approximate formula and mass: C6H8O3; MW ~128.13 g/mol (5-acetyl-2(5H)-furanone).
• Physical state: Typically a low-melting solid or high-boiling liquid depending on purity and temperature; many reports describe it as a pale liquid at ambient conditions.
• Functional behavior: Polar aprotic character due to dual carbonyls; miscible with many organic solvents (e.g., esters, ketones, chlorinated solvents) and sparingly soluble to moderately soluble in water, reflecting its lactone core.
• Volatility: Lower than γ-butyrolactone due to added acetyl functionality; may distill under reduced pressure to avoid thermal decomposition.

Important:

• Do not treat literature values as specifications. For exact property limits relevant to your lot (e.g., density at 20 °C, GC purity, residual solvents), consult the Aladdin CoA/Spec Sheet for SKU A1068529.

Quality and Grades

Item-specific quality information (grade, purity, stabilizers): Not specified for this item; refer to CoA/Spec Sheet.

How to interpret typical grades for this compound class (general guidance):

• Research grade/technical grade: Suitable for most synthetic applications where trace impurities do not impact reaction outcome. Expect GC/HPLC purity typically ≥95%, but confirm by CoA.

• 98% or ≥99% (high-purity) grade: Preferred for structure–activity studies, kinetic experiments, or when used as a building block in medicinal chemistry to reduce impurity carryover.

• Water and volatiles: Lactones can absorb limited moisture; Karl Fischer water and residual solvent levels, when reported, help assess suitability for moisture-sensitive transformations (e.g., strong-base enolizations). If not listed, test in-house as needed.
• Stabilizers: None are typically needed for 5-acetyloxolan-2-one. If a stabilizer is present in a particular lot, its identity/concentration will be listed on the CoA; assess for downstream compatibility.

What is specific to this item:

• Because grade/purity are not provided in the Product Data for SKU A1068529, please consult the Aladdin CoA/Spec Sheet for lot-specific assay, GC/HPLC profile, residual solvents, and any additional quality attributes relevant to regulated workflows.

Reaction and Applications

Research Use Note: For research use only (per Product Data).

Typical synthetic applications for 5-acetyloxolan-2-one (literature/general):

• Enolate chemistry at the acetyl group: The methyl ketone permits formation of a stabilized enolate that undergoes aldol additions to aldehydes/ketones, providing β-hydroxy ketones. Subsequent dehydration can yield α,β‑unsaturated systems conjugated to the butyrolactone (butenolide) core.
• Knoevenagel/Claisen-type condensations: With activated carbonyl partners and bases (e.g., piperidine, ammonium acetate, NaOEt), furnishing arylidene/butenolide frameworks frequently found in flavors and natural product analogs.
• Electrophilic substitution at the ring α‑position to the lactone carbonyl: Under strong base, the ring methylene next to the lactone carbonyl can be deprotonated, enabling alkylation or acylation to diversify substitution patterns.
• Nucleophilic ring opening: Alcohols or amines open the lactone to hydroxyesters or hydroxyamides, enabling access to 4‑hydroxy acid derivatives bearing a distal acetyl moiety; this is valuable for polymer precursors and fine-chemical intermediates.
• Reductions and hydrogenations: Selective reduction of the ketone (NaBH4, catalytic hydrogenation) affords secondary alcohols; stronger reductants (e.g., LiAlH4) can open/reduce the lactone to diols or dihydroxy esters.
• Halogenation/oxidation: α‑Halogenation of the acetyl group (NBS/NCS under acidic or radical conditions) or Baeyer–Villiger oxidation at the ketone offers access to further functional diversification.

Application domains: fragrance/flavor intermediates (butenolides), medicinal chemistry scaffolds (lactone–ketone hybrids), and building blocks in diversity‑oriented synthesis.

Reaction Conditions

General, literature-based guidance (not item-specific; optimize for your system):

• Enolate/aldol at the acetyl group:

  • Base/solvent: LDA or NaHMDS (1.1–1.5 eq) in anhydrous THF, 2‑MeTHF, or toluene. Typical temperatures: −78 to −20 °C for enolate formation; 0 to 25 °C for electrophile addition.
  • Electrophiles: Aldehydes, isocyanates, chloroformates, or silyl chlorides (for TMS enol ether formation).
  • Workup: Quench with NH4Cl at low temperature, extract into EtOAc; silica gel chromatography using EtOAc/hexanes.

• Knoevenagel condensations to butenolides:

  • Conditions: Aromatic aldehyde (1.0 eq), 5‑acetyloxolan‑2‑one (1.2–1.5 eq), catalytic piperidine or ammonium acetate, solvent EtOH or toluene; 50–110 °C, 2–12 h. Water removal (Dean–Stark) may drive equilibrium.

• Ring opening (alcoholysis/aminolysis):

  • Acid-catalyzed: ROH (solvent/reagent), 1–5 mol% p‑TsOH or Amberlyst‑15, 25–80 °C, 1–6 h.
  • Base-catalyzed: NaOMe/MeOH or amine nucleophile (2–3 eq) in DCM/MeOH, 0–25 °C to limit over‑reaction; monitor by TLC/GC.

• Selective ketone reduction:

  • NaBH4 (1.1–1.5 eq) in MeOH/EtOH at 0–25 °C, 0.5–2 h; quench with NH4Cl. Alternatively, H2 (1–5 bar) with Pd/C (5–10 wt%) in EtOAc/iPrOH at rt–40 °C.

• α‑Halogenation at ketone:

  • NBS/NCS (1.0–1.2 eq) with acid catalysis (HBr/HCl traces) in AcOH or DCM, 0–25 °C; protect the lactone from ring opening by avoiding strong base.

Notes: Times, temperatures, and yields are highly substrate- and scale-dependent; verify on small scale and consult primary literature before scale‑up.

Safety and Handling

Item-specific hazard information provided: Not specified (Signal Word, H‑statements, GHS class, pictograms not provided in Product Data). Always consult the SDS for authoritative hazard and precautionary statements.

General safety considerations for 5-acetyloxolan-2-one (literature/general):

• Likely hazards: Combustible organic liquid/low-melting solid; may cause skin/eye irritation; harmful if swallowed or inhaled. Lactones and ketones can be irritants.
• Peroxide formation: Not typically a peroxide-forming class; nonetheless, good storage hygiene (tightly closed containers, away from light/air) is recommended.
• Hydrolysis: Lactones can slowly hydrolyze under strong basic or acidic conditions; avoid contact with strong bases/acids during storage to prevent ring-opening and pressure build-up from CO2 evolution in certain downstream reactions.

Handling and PPE:

• Use in a chemical fume hood.
• Wear lab coat, safety glasses or goggles, and appropriate chemical-resistant gloves (e.g., nitrile). Avoid skin contact and inhalation of vapors/aerosols.

Incompatibilities (general):

• Strong bases (promote ring opening), strong acids (acid-catalyzed hydrolysis), strong oxidizers (may oxidize the ketone or ring), and strong reducing agents (risk of over-reduction of carbonyls).

First aid (overview; defer to SDS):

• Inhalation: Move to fresh air; seek medical attention if symptoms persist.
• Skin/eyes: Rinse with water for at least 15 minutes; remove contaminated clothing; get medical advice if irritation continues.
• Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.

Storage (per Product Data): Room temperature; keep container tightly closed, dry, and protected from light/heat.

Solvent Selection

This product is a small-molecule building block (lactone/ketone), not a solvent. Therefore, “solvent selection” typically pertains to choosing a medium for reactions or processing involving 5-acetyloxolan-2-one, rather than selecting this compound as a solvent.

General guidance (literature/experience-based):

• Polarity compatibility: The molecule is polar aprotic, dissolving well in common organic solvents (e.g., acetonitrile, acetone, ethyl acetate, methanol, dichloromethane, THF). Solubility in hexanes may be limited.
• Reaction media choices:
  • Enolate chemistry (aldol/Claisen at the acetyl group): Use dry, polar aprotic solvents (THF, MTBE, toluene, or DME) with strong bases (LDA, NaHMDS). Low temperature improves selectivity.
  • Nucleophilic ring opening (alcoholysis/aminolysis): Conduct in the nucleophile as solvent or in a co-solvent (MeOH/EtOH/IPA, or DCM with added amine/alcohol) with catalytic acid/base.
  • Hydrogenation/reduction of carbonyl(s): Employ alcohols (EtOH, iPrOH) or ethyl acetate with heterogeneous catalysts; avoid basic conditions that promote ring opening unless desired.
• Workup/extraction: Ethyl acetate or MTBE facilitate phase separation; the lactone generally partitions into the organic phase at neutral pH but may migrate under basic conditions if ring-opened to carboxylates.

For chromatography, start with EtOAc/hexanes gradients; add small percentages of MeOH for polar impurities as needed.

Storage and Reconstitution

Item-specific storage: Room temperature (per Product Data). Keep tightly closed in a dry, well‑ventilated place. Store away from strong acids/bases and oxidizers.

General handling/storage guidance:

• Moisture sensitivity: Lactones can hydrolyze under strongly acidic/basic aqueous conditions; store in tightly sealed containers to limit adventitious moisture. Desiccant storage is optional but helpful in humid environments.
• Light/heat: Protect from excessive heat and direct light to minimize unintended reactions (e.g., self‑condensation or slow hydrolysis).
• Inert atmosphere: Not required, but nitrogen/argon blanket may improve long‑term stability of opened containers.

Reconstitution: Not applicable. This product is supplied neat (no reconstitution buffer or solvent specified). If a solution is required for your workflow, prepare fresh in a suitable dry solvent (e.g., THF, EtOAc, MeOH, ACN) immediately before use. Filter if particulate matter is observed.

Stability/testing: For critical applications, verify identity/purity by NMR/GC/MS prior to use, especially after prolonged storage. Consult the Aladdin CoA/Spec Sheet for any lot‑specific storage notes or retest intervals.

Structure and Identity

Item-specific identifiers (from Product Data):

• SKU: A1068529
• Product name: 5-Acetyloxolan-2-one
• CAS: 29393-32-6
• InChIKey: 5668 (as provided)
• Storage: Room temperature

Literature/computed identity (general reference; not item-specific):

• Synonyms: 5-Acetyl-2(5H)-furanone; 5-Acetyl-γ-butyrolactone (ABL); 5-Acetyl-dihydrofuran-2-one
• Molecular formula (literature): C6H8O3
• Molecular weight (literature): ~128.13 g/mol
• Structural class: Five-membered cyclic ester (γ-butyrolactone) bearing a pendant acetyl (–COCH3) substituent at the ring’s C-5 position.
• Core functional groups: Lactone carbonyl (cyclic ester), ketone (acetyl). No stereocenters; achiral.
• Qualitative 2D description: A five‑membered ring containing one ring oxygen and a lactone carbonyl at C-2 (oxolan-2-one). The carbon adjacent to the ring oxygen on the opposite side (C-5) is substituted with a –COCH3 group. This places two carbonyls in a 1,4‑relationship through the ring framework.

Notes:

• SMILES/InChI not specified for this item; refer to CoA/Spec Sheet.
• Where literature data are provided above, they are for general reference only and are not specifications for this catalog item.

Synthetic Utility

Key reactive elements:

• Dual carbonyl functionality: A γ‑butyrolactone ring (activated cyclic ester) and an exocyclic methyl ketone (acetyl substituent) provide complementary reactivity.
• Enolizable positions: The acetyl α‑methylene is readily deprotonated to form a stabilized enolate for C–C bond construction. Under stronger base, deprotonation α to the lactone carbonyl is also feasible, allowing orthogonal functionalization.

Representative transformations (literature/general):

• Aldol/Knoevenagel condensations: Enolate formation followed by addition to aldehydes affords β‑hydroxy ketones; dehydration gives arylidene‑butenolides, common in flavors and bioinspired scaffolds.
• Nucleophilic ring opening: Alcoholysis/aminolysis yields 4‑hydroxyesters or 4‑hydroxyamides that retain the distal ketone, enabling further elaboration (e.g., reductive amination, acylation, cyclization to new ring systems).
• Selective reductions: NaBH4 or catalytic hydrogenation reduces the ketone to secondary alcohols; chemoselectivity can be tuned to preserve the lactone. Strong hydrides (LiAlH4) open/reduce the lactone to diols.
• Halogenation/oxidation: α‑Halogenation at the ketone (e.g., via NBS/NCS under acid) followed by substitution; Baeyer–Villiger on the ketone to generate ester variants; epoxidation of enone products from condensations.
• Metal-catalyzed couplings: Enol triflate formation from the ketone enables subsequent Suzuki/Negishi couplings to install aryl/vinyl groups, expanding diversity.

Retrosynthetic value: The molecule can be traced back to γ‑butyrolactone and acetylating/oxidizing equivalents, or assembled from levulinic acid derivatives via cyclization, offering flexible entry points for route scouting.

Target Specificity

Not applicable. This product is a small organic molecule and not a biological reagent (e.g., antibody, enzyme, or probe) with defined target specificity. No antigen/epitope, clone, isotype, or species reactivity information applies.

Perguntas frequentes

What is the purity of this product?

This product is supplied at ≥95% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.

How should this product be stored?

Store at room temperature.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 29393-32-6, the molecular formula is C6H8O3, and the molecular weight is 128.13 g/mol. InChIKey AHLDCEZSQNGEFT-UHFFFAOYSA-N.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.