3-Acetylcoumarin - Moligand™, 10 mM in DMSO , CAS No.3949-36-8

CAS: 3949-36-8 Cat. No.: A1496674 Summenformel: C₁₁H₈O₃ Molekulargewicht: 188.18 Beilstein Registry Number: 17(5)11,367

GRADE & PURITY Moligand™, 10 mM in DMSO

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Übersicht

3-Acetylcoumarin (Compound 4) has acaricidal activity against Tetranychus cinnabarinus.

Specifications

Spezifikationen & Reinheit

Moligand™, 10 mM in DMSO

Storage

Store at -80°C

Verschickt in

Dry ice packs + Cold packs

Dieses Produkt erfordert Kühlkettenversand. Grundversand und andere Economy-Optionen sind nicht verfügbar.

Note

Moligand™

Aktionsart

INHIBITOR

Namen und Kennungen

• Isomere SMILES: CC(=O)C1=CC2=CC=CC=C2OC1=O
• WGK Deutschland: 3
• Molekulargewicht: 188.18
• Beilstein: 17(5)11,367
• Reaxy-Rn: 143498
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=143498&ln=

Chemische und physikalische Eigenschaften

• Schmelzpunkt (°C): 123 °C

Referenzen

1. Brian Musikavanhu, Tingting Pan, Quanhong Ma, Yongdi Liang, Zhaoli Xue, Lei Feng, Long Zhao.  (2024)  Dual detection of Hg2+ and Pb2+ by a coumarin-functionalized Schiff base in environmental and biosystems.  SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY,      [PMID:38447440] [10.1016/j.saa.2024.124101]

Application Protocols

No item-specific, validated application protocols are provided for this SKU. The following general protocols can guide typical research uses of small molecules like 3-acetylcoumarin:

• Preparation of screening stock solutions (general):

  • Dissolve to 10–50 mM in dry DMSO. Sonication or gentle warming (≤40 °C) may aid dissolution. Filter (0.22 µm PTFE) if particulate is observed.
  • Store aliquots at the recommended temperature to avoid repeated freeze–thaw.
  • For assays, dilute into buffer to a final DMSO content ≤0.5–1.0% v/v.

• Small-scale aldol/Knoevenagel reaction setup (general):

  • Combine 3-acetylcoumarin (1.0 eq), aromatic aldehyde (1.1 eq), ethanol (0.1–0.2 M), and piperidine (10 mol%). Stir at rt–reflux 2–6 h; monitor by TLC (UV). Quench with dilute acid, cool, collect precipitated product, wash, and dry.

• Analytical QC (general):

  • NMR: acquire 1H/13C in DMSO-d6 or CDCl3; look for two carbonyl signals (~160–175 and ~190–200 ppm in 13C, literature/general).
  • LC–MS: reverse-phase C18, ACN/H2O + 0.1% formic acid gradient; monitor UV at 254/280 nm.

These are general examples only; adjust conditions based on your substrates and instrumentation. For any safety-critical operations, consult the SDS and institutional SOPs.

Biological Roles

No specific biological role or target engagement is assigned to this item in the product data. The following points provide general, non-clinical context for the coumarin/3-acylcoumarin chemical class in biochemical research:

• Photophysics and probes (general): Coumarin chromophores exhibit strong absorption in the near-UV and fluorescence in the blue–green region. Substitution at the 3-position with an acetyl group modulates intramolecular charge transfer (ICT), enabling tuning of emission and environmental sensitivity—useful in designing solvatochromic or reaction-based fluorescent probes.
• Enzyme interaction studies (general): Coumarin derivatives are frequently used as reporter substrates (e.g., 7-amino- or 7-hydroxycoumarin conjugates). While 3-acetylcoumarin itself is a scaffold rather than a typical reporter, it can serve as a precursor to functionalized coumarins for enzyme assays.
• Binding studies and screening (general): As an aromatic, planar, moderately lipophilic small molecule, 3-acetylcoumarin can be included in screening libraries to explore π–π stacking and hydrogen bond-acceptor interactions (two carbonyls) in protein pockets.
• Metabolic considerations (general): In biological systems, coumarin cores may undergo oxidative metabolism (aromatic hydroxylation) and lactone hydrolysis; aryl methyl ketones can be reduced or transformed to oximes/hydrazones in chemical biology workflows. These are chemical transformations and not therapeutic claims.

Note: This product is supplied strictly for research use only. No implications of therapeutic efficacy, safety in humans/animals, or clinical usage should be drawn from the above general chemical biology context.

Buffer Applications

This compound is a neutral, poorly water-soluble aromatic solid and is not used as a buffering agent. It lacks acid–base pairs with pKa values suitable for aqueous buffering.

Practical guidance:

• For aqueous assay systems involving 3-acetylcoumarin, prepare concentrated stocks in DMSO or ethanol and dilute into the target buffer (e.g., PBS, HEPES) keeping final organic solvent ≤1% v/v to maintain assay integrity (general).
• If conjugation or probe synthesis is planned, perform coupling steps in organic media and only introduce the product into buffer after suitable derivatization to enhance solubility.

If you require buffer recipes or pH ranges, refer to standard biological buffers (PBS pH 7.4, HEPES pH 7.2–7.6, Tris pH 7–9); these are unrelated to the buffering capacity of 3-acetylcoumarin itself.

Green Alternatives

Sustainable choices around 3-acetylcoumarin focus primarily on solvent selection and catalytic conditions, as the substrate itself is a specialty aromatic. Consider the following greener options (general guidance):

• Reaction media:

  • Replace chlorinated solvents (CH2Cl2/CHCl3) with ethyl acetate, 2-MeTHF, or anisole for workups and extractions where feasible.
  • For base-catalyzed condensations, use ethanol or water–ethanol mixtures with organocatalysts (e.g., piperidine, L-proline) instead of strong inorganic bases.
  • Employ solvent-free or mechanochemical protocols (ball milling) for aldol/Knoevenagel reactions to cut solvent use (literature reports for coumarin ketones).

• Catalysis and energy:

  • Heterogeneous bases (e.g., KF/alumina, basic zeolites) enable easier separation/reuse.
  • Microwave or ultrasound assistance can shorten reaction times and reduce energy consumption.

• Workup and purification:

  • Favor crystallization from green solvents (EtOH, iPrOAc) over chromatographic purification when possible.

Compact comparison (general):

• Traditional: NaOH in MeOH, CH2Cl2 workups, silica flash.
• Greener: K2CO3 or organic base in EtOH–water, EtOAc extraction, direct crystallization.

Trade-offs:

• Greener solvents may change selectivity or rates; slight temperature increases or longer times may be required.
• High-throughput screening stocks in DMSO remain common; consider minimizing final DMSO content (<1% v/v) in biological assays to reduce solvent impact.

Pharmaceutical Uses

No pharmacopeial status, excipient role, or GMP-related use is provided for this item. It is supplied as a research chemical only (Research Use Only).

Context (general, non-clinical):

• Coumarin scaffolds are widely explored in medicinal chemistry as privileged structures due to their planarity and dual carbonyl hydrogen-bond acceptors. 3-Acetyl substitution provides an enolizable handle for rapid SAR elaboration (e.g., formation of chalcone-like extensions or heterocycle annulations).
• In formulation science, neutral aromatic solids with limited aqueous solubility like 3-acylcoumarins are typically dissolved in co-solvents (DMSO, PEG 400, ethanol) for in vitro studies only; no claims are made for clinical formulation suitability.

Regulatory note:

• This product is not intended for use in humans or animals, is not an API or excipient, and carries no USP/EP/JPE monograph. Any development beyond bench research would require independent qualification and regulatory assessment by the user.

Physical Properties

Item-specific numerical specifications (mp, bp, density, UV cutoff, water content, residual metals) are Not specified for this item; refer to CoA/Spec Sheet.

Literature/General (for the coumarin/3-acylcoumarin class; provide context only):

• Phase/appearance: typically a crystalline solid for many 3-acylcoumarins; color off-white to pale yellow depending on impurity and conjugation (literature, general).
• Melting point: often in the low-to-mid 100s °C for 3-acylcoumarins; specific value varies with purity and polymorph (literature, general).
• Boiling point: thermal decomposition may precede boiling under ambient pressure; distillation is generally not used (general).
• Solubility:
  • Organic: soluble in polar aprotic media (DMSO, DMF, NMP) and moderately in alcohols and chlorinated solvents (literature, general).
  • Aqueous: low water solubility expected for neutral coumarin ketones (general).
• LogP/logD: moderately lipophilic for aryl–lactone–ketone frameworks (general qualitative assessment).
• pKa: no ionizable basic centers; very weak acidity possible from enolizable methylene of the acetyl (tautomeric enol) but not typically titratable in water (general).
• Spectroscopy: conjugated coumarins exhibit strong UV absorption in near-UV; many display blue-green fluorescence depending on substitution and solvent polarity (literature, general).

Practical notes:

• Prefer gravimetric handling; avoid prolonged exposure to ambient moisture and light to minimize degradation or coloration (general practice for coumarins).
• For analytical characterization, 1H/13C NMR in DMSO-d6 or CDCl3 and HRMS are routine; strong carbonyl bands appear in IR (~1700–1750 cm−1 region, literature/general).

Quality and Grades

• Item Grade: Moligand™ (as provided). This designation indicates inclusion in a curated small-molecule/compound library intended for discovery, screening, and ligand- or probe-oriented research workflows. While not a regulated pharmacopeial grade, Moligand™ emphasizes compound identity, suitability for biochemical screening, and reliable handling formats for high-throughput or fragment-to-lead campaigns.

What Moligand™ typically implies (general program description):

• Emphasis on structural identity confirmation (e.g., NMR/MS) to support screening data integrity.
• Packaging suitable for screening logistics (e.g., smaller vials, plate-compatible aliquots where applicable). Exact pack format for this SKU is Not specified for this item; refer to CoA/Spec Sheet.
• No promise of low-UV or trace-metal specifications unless explicitly stated. For any numeric impurity limits (water, peroxide, metals, residual solvents), Not specified for this item; refer to CoA/Spec Sheet.

Comparison to other common grades (context):

• Analytical/AR grade targets general analytical use, not necessarily low-background in bioassays.
• HPLC grade solvents focus on UV/fluorescence background and particulate; not applicable to this solid building block.
• Pharmacopeial (USP/EP) grades include compendial tests for APIs/excipients—this product is for research use only and not supplied under pharmacopeial monographs.

Stabilizers/additives: None stated. If stabilizers or formulating excipients are used, these would be listed on the CoA; currently, Not specified for this item; refer to CoA/Spec Sheet.

Reaction and Applications

As a 3-acylated coumarin, 3-acetylcoumarin is a versatile synthon that combines an enolizable aryl methyl ketone with a conjugated lactone. Key research applications include:

• Aldol/Claisen–Schmidt condensations (literature):
  • The acetyl group undergoes base- or amine-catalyzed condensations with aromatic or heteroaromatic aldehydes to furnish 3-(arylideneacetyl)coumarins. Bases such as NaOH, K2CO3, piperidine, or morpholine in EtOH, MeOH, or EtOH–water are common.
• Knoevenagel-type couplings (literature):
  • In the presence of secondary amines or ammonium acetate, the activated methylene adjacent to the acetyl carbonyl couples with aldehydes to build extended push–pull chromophores.
• Michael-type reactivity (general):
  • The resulting arylidene products can participate in 1,4-additions; the parent 3-acetylcoumarin can act as a soft electrophile after activation, though the lactone is generally less prone to nucleophilic opening under neutral conditions.
• Cyclizations and annulations (literature):
  • Intramolecular reactions of condensation products can yield polycyclic coumarin-fused frameworks; acid or Lewis acid catalysis can promote further ring closures.
• Functional-materials precursor (general):
  • Coumarin derivatives are widely used as fluorescent scaffolds; 3-acetyl substitution modulates ICT character, enabling tuning of emission maxima in probe development.
• Metal-catalyzed transformations (literature):
  • Pd-catalyzed direct arylation of coumarins and subsequent acyl manipulations enable rapid SAR. The acetyl can be elaborated to oximes, hydrazones, or reduced to alcohols/alkanes (NaBH4, Wolff–Kishner, Clemmensen under controlled conditions).

Practical tips:

• Maintain anhydrous conditions for base-sensitive steps; lactones can hydrolyze under strong base with extended times.
• Monitor by TLC with UV (254/365 nm); coumarins are strongly UV-active, aiding reaction tracking.

Reaction Conditions

General, literature-informed conditions for common transformations of 3-acetylcoumarin (examples; optimize per substrate):

• Aldol/Claisen–Schmidt-type condensation:

  • Reagents: aromatic aldehyde (1.0–1.2 eq), piperidine (10–20 mol%) or NaOH (10–30 mol%).
  • Solvent: ethanol or methanol; EtOH–water (9:1 to 7:3) often effective.
  • Temperature/time: rt to reflux, 1–12 h depending on aldehyde electronics.
  • Notes: Monitor by TLC (UV); product often precipitates on cooling; neutralize and filter.

• Knoevenagel condensation (amine-catalyzed):

  • Reagents: ammonium acetate or piperidine (cat.), aldehyde.
  • Solvent: ethanol, acetonitrile, or solvent-free (grinding/mechanochemical conditions reported).
  • Temperature: rt to 60 °C; microwaves can reduce times to minutes.

• Oxime/hydrazone formation:

  • Reagents: hydroxylamine hydrochloride or hydrazine derivatives (1.1–1.5 eq), base (pyridine/Et3N or AcONa), ethanol or MeOH.
  • Temperature: rt to reflux, 1–4 h.

• Selective reduction of acetyl group:

  • Reagents: NaBH4 (1–2 eq) in MeOH/EtOH at 0 °C to rt; quench carefully. Lactone reduction is slower; Luche conditions (NaBH4/CeCl3) can enhance carbonyl selectivity.

• Lactone ring-opening (avoid unless intended):

  • Strong base (NaOMe, KOH) in alcohols and heat can open the lactone; neutralization reforms the ring, but side reactions may occur.

Yields are substrate-dependent; typical isolated yields in literature for condensations range from moderate to high when optimized. Always confirm identity by NMR/HRMS and assess purity by HPLC/UPLC before downstream use.

Safety and Handling

GHS classification, signal word, pictograms, and H-statements: Not specified for this item; refer to SDS for authoritative safety information.

General coumarin/aryl-ketone handling guidance (for laboratory research use only):

• Likely hazards: organic solids of this class may cause skin/eye irritation and may be harmful if swallowed or inhaled; dust can be irritating (general). Avoid generating dust/aerosols.
• Personal protective equipment (PPE): laboratory coat, safety glasses or chemical splash goggles, and appropriate chemical-resistant gloves (e.g., nitrile). Use in a fume hood to control vapors/dust.
• Incompatibilities: strong bases (can induce ring-opening transesterification of lactones or aldol reactions at the acetyl), strong acids (hydrolysis), strong oxidizers (oxidative degradation). Avoid prolonged exposure to light and heat (general for conjugated aromatics/lactones).
• Peroxide formation: not an ether; peroxide formation is not a typical hazard (general).
• First aid (overview; defer to SDS):
  • Skin: wash with soap and water; remove contaminated clothing.
  • Eyes: rinse cautiously with water for several minutes; remove contact lenses if present and easy; seek medical advice if irritation persists.
  • Inhalation: move to fresh air; seek medical attention if symptoms occur.
  • Ingestion: rinse mouth; do not induce vomiting; get medical attention as needed.
• Fire safety: treat as combustible organic solid; use CO2, dry chemical, or foam; avoid high-temperature decomposition which can emit irritating fumes (general).
• Waste: collect organic solid waste in appropriate containers; dispose according to institutional and local regulations.

Solvent Selection

Given its neutral, conjugated lactone–ketone framework, 3-acetylcoumarin behaves as a moderately polar, largely aromatic solid with low aqueous solubility and good solubility in polar aprotic solvents.

• Preferred dissolution for stock solutions:
  • DMSO: excellent solubility; ideal for biochemical screening stocks.
  • DMF/NMP: also strong solvents for preparative reactions and NMR.
  • Ethanol/MeOH/2-PrOH: moderate to good solubility; useful for recrystallization and reactions where protic media aid enolization.
  • CH2Cl2/CHCl3/EtOAc: moderate solubility; suitable for chromatography and extractions.
  • Water: poor solubility expected; use cosolvents for aqueous assays (general).

Selection guidance (general):

• For base-catalyzed condensations (e.g., aldol/Knoevenagel), EtOH, MeOH, or EtOH–water with catalytic piperidine or NaOH are commonly used (literature).
• For electrophilic substitutions or acylations on the aromatic ring (less common here), POCl3, polyphosphoric acid, or Lewis acids require chlorinated or nitro solvents; handle with care.
• For photophysical measurements, choose spectroscopic-grade MeCN, MeOH, or DMSO to minimize background.

Quick comparison (general):

• DMSO vs DMF: DMSO offers superior biocompatibility in assay stocks (≤1% v/v final), whereas DMF may interfere in some enzymatic assays.
• EtOH vs MeOH in condensations: EtOH is safer/greener and often affords similar outcomes; MeOH can increase rates but raises toxicity concerns.
• EtOAc/Hexane systems: effective for flash chromatography; add a small amount of CH2Cl2 to improve elution of strongly adsorbed coumarins.

Storage and Reconstitution

• Storage conditions (item-specific): Store at -80°C (per product data). Protect from light and moisture.
• Shipping (item-specific): Shipped on dry ice packs + cold packs to maintain low temperature during transit.
• Container handling: Upon receipt, keep sealed until equilibration to prevent condensation. Open in a low-humidity environment; reseal promptly (preferably under inert gas) with desiccant present.

Reconstitution and working solutions (general guidance):

• Solvent choice: Prepare concentrated stocks in anhydrous DMSO (typical 10–50 mM) or DMF. Ethanol can be used for chemistry workflows; ensure compatibility with downstream assays.
• Aliquoting: Divide into single-use aliquots to minimize freeze–thaw cycles. Clearly label concentration, solvent, and date.
• Stability: Item-specific stability data are Not specified for this item; refer to CoA/Spec Sheet. As a general practice for coumarin ketones, avoid prolonged exposure to elevated temperature and light to minimize degradation or discoloration.
• Freeze–thaw: Minimize cycles; thaw quickly at room temperature, use immediately, and return any remaining stock to -80°C. Do not store long-term at bench.
• Solid-state handling: If weighing at room temperature, limit time out of the freezer; allow the sealed vial to warm to ambient before opening to prevent moisture uptake.

Always refer to the product’s SDS and any accompanying specification sheet for definitive handling and stability information.

Structure and Identity

3-Acetylcoumarin is an aromatic lactone (coumarin core) bearing an additional ketone (acetyl) at the 3-position, yielding a conjugated bicyclic system with two carbonyls in conjugation with a benzene ring.

• Synonyms: 3-acetyl-2H-1-benzopyran-2-one; 3-acetylchromen-2-one (literature)
• Core features:
  • Coumarin (chromen-2-one) scaffold: benzopyran-2-one fused system (one lactone carbonyl).
  • Acyl substituent at C-3: a ketone (–COCH3) conjugated to the lactone and aromatic ring, enhancing electron withdrawal and enabling enolate chemistry.
  • Planarity: largely planar, promoting strong π–π interactions and characteristic coumarin photophysics (general).
• Functional groups:
  • Lactone (cyclic ester) carbonyl at C-2.
  • Aryl ketone (acetyl) at C-3; enolizable methyl.
• Stereochemistry: None (achiral, no stereocenters; planar aromatic system).
• Molecular formula: Not specified for this item; refer to CoA/Spec Sheet. (Typical literature assignment for 3-acetylcoumarin: C11H8O3.)
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet. (Typical literature value: ~188.18 g/mol.)
• SMILES: Not specified for this item; refer to CoA/Spec Sheet. (Common literature representation includes a coumarin core with an acetyl at C-3.)
• InChIKey: Not specified for this item; refer to CoA/Spec Sheet.

2D structure in words (general): a benzene ring fused to an α-pyrone (lactone) ring; at the junction carbon (position 3 of coumarin) a carbonyl-bearing acetyl group projects outward, forming an aryl–vinyl–carbonyl conjugation path across the scaffold.

Synthetic Utility

3-Acetylcoumarin is a dual-carbonyl synthon integrating:

• A lactone carbonyl (conjugated ester) that can engage in selective reductions (e.g., DIBAL-H to lactol) or ring-opening under strong nucleophilic/basic conditions.
• An aryl methyl ketone enabling enolization and C–C bond formation.

Representative transformations (literature/general):

• Aldol/Claisen–Schmidt condensations with aldehydes → 3-(arylideneacetyl)coumarins (chromophoric extensions). Catalysts: secondary amines (piperidine), ammonium salts, or weak bases (K2CO3) in EtOH or MeOH.
• Oxime/hydrazone formation at the acetyl carbonyl → handles for further cyclizations (e.g., to isoxazoles or pyrazoles under oxidative/cyclodehydrative conditions).
• Reductive manipulations: NaBH4 or Luche conditions to reduce the acetyl group to the corresponding secondary alcohol; Wolff–Kishner/Clemmensen to deacylate or convert to the methyl unit (conditions must be balanced to preserve the lactone).
• Electrophilic aromatic substitutions on the benzene ring (activated/deactivated depending on position); directed metalation can be employed on suitably protected derivatives.
• Cross-coupling on pre-halogenated coumarin rings synthesized from 3-acetylcoumarin precursors enables fast SAR build-outs (Pd-catalyzed Suzuki/Heck; C–H activation protocols are reported for coumarins).

Retrosynthetic value:

• Serves as a convergent node between a salicylaldehyde-derived lactone and an acetyl synthon; many target scaffolds in dyes and probes can be traced back to 3-acetylcoumarin as a late-stage branching point.

Target Specificity

Not applicable. This product is a small-molecule chemical and not a biological macromolecule or affinity reagent. No antigen, epitope, isotype, or species reactivity applies. Item-specific binding targets are Not specified for this item; refer to published literature if using 3-acetylcoumarin as a scaffold in target-based screening.