4-acryloylphenol - Moligand™, ≥97% , Inhibitor of 4-aminobutyrate aminotransferase;Inhibitor of aldehyde dehydrogenase 5 family member A1, CAS No.95605-38-2, Inhibitor of 4-aminobutyrate aminotransferase;Inhibitor of aldehyde dehydrogenase 5 family member A1
4-acryloylphenol - Moligand™, ≥97% , Inhibitor of 4-aminobutyrate aminotransferase;Inhibitor of aldehyde dehydrogenase 5 family member A1, CAS No.95605-38-2, Inhibitor of 4-aminobutyrate aminotransferase;Inhibitor of aldehyde dehydrogenase 5 family member A1
GRADE & PURITYMoligand™?Moligand™ — Aladdin's line of ligands and bioactive small molecules. Use for receptor, pathway, and binding studies needing defined small-molecule tools.≥97%
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Application Protocols
No application protocols, tested assay types, or recommended dilutions are provided in the Product Data for this small-molecule library member.
General handling for screening (research-use guidance):
Prepare concentrated stock solutions in anhydrous DMSO (e.g., 10–50 mM), filter if necessary (0.2 μm PTFE), aliquot, and store frozen. Thaw immediately before use and avoid repeated freeze–thaw cycles.
For biochemical/cellular assays, limit final DMSO to ≤1% v/v where compatible, and prepare working solutions fresh to minimize Michael addition with buffer components.
Verify identity and purity by LC–MS/HPLC prior to critical experiments, and include stability controls over the assay timeframe.
For detailed, method-specific protocols, consult primary literature relevant to α,β-unsaturated aryl ketones or contact our technical support with your intended application.
Biological Roles
Item-specific biological roles are not provided. The following are general, literature-based considerations relevant to phenolic α,β-unsaturated ketones; they are offered for research context only and not as medical or clinical claims.
Electrophilic probe behavior (general):
α,β-Unsaturated carbonyls are classical Michael acceptors that can form reversible or irreversible adducts with nucleophilic amino acid side chains (notably cysteine and, less strongly, lysine/histidine). This property underlies use in covalent ligand discovery and chemical biology target engagement studies (research use only).
Phenolic motif:
Phenolic groups can participate in hydrogen bonding and influence redox behavior. Para-hydroxylation can modulate π–π stacking and binding orientation in protein pockets (general observation from SAR literature of phenolic aromatics).
Metabolic considerations (general):
Typical biotransformations for aryl enones/phenols include conjugate reduction, epoxide formation on the vinyl group (P450-mediated for analogous systems), phenolic O-glucuronidation/sulfation, and oxidative coupling/polymerization under strong oxidative stress conditions.
Assay handling notes (practical):
Prepare fresh DMSO stocks and minimize exposure to thiol-containing assay buffers to prevent off-target Michael addition. Include orthogonal readouts (e.g., covalent adduct MS) when studying protein reactivity.
No target specificity or bioactivity data are provided for this catalog entry; consult primary literature for mechanistic studies on related aryl enones.
Buffer Applications
This compound is not a buffering agent and is not typically used to prepare biochemical buffers. It lacks conjugate acid/base pairs with pKa values in the physiological buffering range that would provide significant buffer capacity.
Practical guidance:
If solutions are required for biochemical assays, dissolve in a suitable co-solvent (commonly DMSO) and dilute into the working buffer immediately before use. Avoid high concentrations of nucleophiles (e.g., primary amines, excess thiols) which may react with the enone.
For any pH-dependent studies, select an appropriate buffer system separately (e.g., phosphate, HEPES, Tris) and verify compound stability at the chosen pH.
No buffer recipes or pH range data are applicable to this item.
Green Alternatives
Sustainability considerations for working with 4-acryloylphenol mainly concern solvent choices and process conditions, as the molecule’s core functionality (aryl enone/phenol) is intrinsic.
Greener solvent substitutions (general guidance):
Replace DMF with: Cyrene (dihydrolevoglucosenone) or propylene carbonate where compatible with base/nuclophile and solubility.
Replace THF with: 2-MeTHF or cyclopentyl methyl ether (CPME) to reduce peroxide risk and improve solvent life-cycle metrics.
Replace dichloromethane with: ethyl acetate or methyl tert-butyl ether (MTBE) for extractions/chromatography when polarity allows.
Illustrative comparison (general; not item-specific):
THF vs 2-MeTHF: similar polarity; 2-MeTHF is partly bio-based, less miscible with water (easier phase splits), and more stable toward peroxide formation.
DMF vs Cyrene: Cyrene offers comparable dipolarity with a more favorable environmental profile; verify base compatibility and reaction rates.
Process intensification:
Conduct Michael additions under solvent-minimized or micellar conditions (e.g., aqueous TPGS-750-M) when feasible to reduce organic solvent use.
Employ catalytic, chemoselective reductions (e.g., transfer hydrogenation with Hantzsch ester) instead of stoichiometric hydrides.
Waste minimization:
Phenol/enone-containing waste can be reactive; quench nucleophiles before disposal and segregate halogen-free streams. Optimize chromatography to reduce solvent volumes (use gradient or supercritical CO2 where possible).
Pharmaceutical Uses
No pharmacopeial status or excipient role is provided for this product. The following comments are general and for research/manufacturing context only (not therapeutic claims):
Typical roles for similar small molecules:
As synthetic intermediates in medicinal chemistry programs, α,β-unsaturated aryl ketones can be diversified into β-amino ketones, saturated ketones/alcohols, and heterocycles, supporting lead optimization workflows.
The phenolic OH offers a handle to modulate solubility and permeability through prodrug-like esterification or etherification during research phases.
Formulation considerations (research use):
For in vitro screening, compounds of this class are commonly supplied as DMSO stocks (e.g., 10–50 mM), aliquoted, and stored frozen to minimize freeze–thaw cycles. Verify stability and absence of reactivity with excipients.
Regulatory note:
This product is labeled For research use only and is not intended for human or veterinary use, nor for incorporation into drug products without appropriate development and regulatory oversight.
No pharmacopeial monograph, GMP grade, or clinical-use information is specified for this item.
Physical Properties
Only limited item-specific physical data are provided for this catalog entry. Where values are given below, they are annotated as literature (general reference) rather than product specifications.
Item-specific values (from Product Data):
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/reference values (for context; not specifications):
Expected physical state: low-melting solid or viscous oil is typical for small aryl enones; exact MP/BP not located in primary references for this CAS.
Solubility profile (qualitative, literature):
Water: expected very low solubility due to aromatic core and limited H-bond acceptors.
Organic solvents: typically soluble in polar aprotic media (DMSO, DMF, acetone, acetonitrile) and moderately in less polar solvents (EtOAc, THF, toluene); exact solubilities not found.
UV-vis: conjugated aryl–enone systems commonly show strong absorption in the near-UV (approx. 230–330 nm, literature generality; no item-specific cutoff provided).
LogP/pKa: Specific numerical values not located in reliable sources for this exact compound; phenolic pKa for para-substituted phenols is commonly ~9–10 (literature generality), but the enone substituent may slightly modulate this.
For authoritative numerical specifications (mp, bp, density, refractive index, residual solvents), consult the item’s CoA/Spec Sheet.
Quality & Grades
Item-specific grade: Moligand™ (per Product Data)
Typical meaning (Aladdin Moligand™, general description): library-grade small molecules intended for screening, probe development, and method development in medicinal and chemical biology workflows. Emphasis is on identity, purity suitable for screening, and packaging amenable to high-throughput use.
What this implies for users (general expectations):
Identity confirmation: Typically supported by NMR/HRMS or LC–MS and HPLC/UPLC purity data in the CoA. Exact analytical methods and acceptance criteria are batch-specific. Request CoA for details.
Purity basis: Not specified for this item; refer to CoA/Spec Sheet. Moligand™ entries commonly target high purity conducive to screening, with controlled residual solvents and defined salt/tautomer forms.
Stabilizers: Not specified for this item; refer to CoA/Spec Sheet. Given the α,β-unsaturated ketone, absence/presence of inhibitors (e.g., trace polymerization inhibitors) should be verified on the CoA if critical for your application.
Suitability notes for 4-acryloylphenol:
Reactive handle: The enone motif is electrophilic; purity with respect to Michael adducts or polymerization byproducts may be important for SAR work—review chromatograms on the CoA.
Solid-state form/appearance, water content, metal content, UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.
Suggested QC on receipt (good practice):
Verify identity by LC–MS and purity by HPLC under your method; assess stability in intended storage solvent (e.g., DMSO) by time-course LC–MS.
Reaction & Applications
4-Acryloylphenol combines a conjugated enone (Michael acceptor) with a phenolic handle, enabling both electrophilic and nucleophilic chemistries.
Electrophilic reactivity (general):
Michael addition: soft nucleophiles (thiols, malonates, enolates, secondary amines) add 1,4- to the enone under base or Lewis acid catalysis. This allows rapid diversification into β-substituted ketones.
Conjugate reductions: selective 1,4-reduction (e.g., Hantzsch ester, catalytic hydrogenation) affords saturated aryl ketones; subsequent reductions can convert the ketone to alcohols.
Diels–Alder (inverse electron-demand variants with highly activated dienes) are less common but enones can participate under activation.
Phenolic derivatization:
Etherification: O-alkylation (e.g., K2CO3 or Cs2CO3 in acetone/DMF with alkyl halides) provides para-alkoxy enones.
Esterification: acyl chloride/EDC-type couplings give carbonate/ester derivatives, tuning lipophilicity and reactivity.
Protective strategies: phenolic O-protection (e.g., MOM, Bn, TBDPS) can improve chemoselectivity in multi-step sequences.
Cross-coupling via prefunctionalization:
Although 4-acryloylphenol itself lacks a halogen handle, directed ortho-metalation or prior halogenation of related scaffolds enables Suzuki/Heck/Sonogashira elaboration on the ring while retaining (or transforming) the enone.
Applications (manufacturer context expanded):
As a Moligand™ library member, it can be used in fragment or covalent screening campaigns where enone electrophilicity probes nucleophilic residues in proteins (research use only). It is also a versatile intermediate for synthesizing cinnamyl-like frameworks, β-amino ketones, and conjugated diaryl systems after coupling of derivatives.
Reaction Conditions
General literature-guided conditions for common transformations of aryl enones and phenols are summarized below. These are not product specifications; optimize for your specific system.
Solvents: THF, MeCN, MeOH, or DMF; also feasible in 2-MeTHF or EtOAc with phase-transfer or base.
Bases/catalysts: K2CO3, Et3N, DBU; or Lewis acids (e.g., ZnCl2) for soft activation. Temperatures 0–25°C (often RT). Reaction times: 0.5–12 h depending on nucleophile. Reported isolated yields for analogous aryl enones: 60–95% (literature ranges).
Conjugate reduction/hydrogenation:
Catalysts: Pd/C, Pt/C, or Raney Ni under H2 (1–3 bar) in EtOH/EtOAc at RT–40°C for selective C=C reduction; or organocatalytic transfer hydrogenation (Hantzsch ester) with chiral catalysts for enantioselective variants.
O-alkylation of the phenol:
Conditions: K2CO3 (2–3 equiv) in acetone, acetonitrile, or DMF; alkyl bromide/iodide (1.2–1.5 equiv); 25–60°C, 2–16 h. Phase-transfer (TBAB) in biphasic toluene/H2O is also effective. Typical yields: 70–95% for clean substrates.
Epoxidation of the double bond:
Reagents: mCPBA (1.1–1.5 equiv) in DCM or EtOAc at 0–25°C; quench and isolate epoxide for subsequent ring opening.
Workup/purification tips:
Avoid strong basic washes that can promote addition reactions. Use buffered aqueous workups (e.g., pH 6–7) and rapid silica chromatography with eluents such as hexanes/EtOAc or toluene/EtOAc. Protect from light/air if discoloration is observed.
Safety & Handling
Authoritative source: Always consult the Safety Data Sheet (SDS) for definitive hazards, handling, and first-aid information for this specific lot.
GHS classification (item-specific): Not specified for this item; refer to SDS.
Signal word: Not specified
Hazard statements (H-codes): Not specified
Pictograms: Not specified
General hazard considerations for α,β-unsaturated carbonyls and phenols (literature/general):
May act as electrophilic Michael acceptors toward nucleophiles (e.g., thiols, amines); avoid skin contact and inhalation of dust/vapors.
Phenolic OH can be irritating to skin, eyes, and respiratory tract.
Unsaturated ketones can undergo polymerization or addition reactions; avoid strong bases/acids unless intended.
Storage/incompatibilities (item-specific):
Storage: Store at −20°C (per Product Data). Keep tightly closed under inert atmosphere if possible to limit oxidation and adventitious polymerization.
Incompatibilities (general): strong oxidizers, strong bases or acids (may trigger addition/condensation), nucleophiles (amines, thiols) which can add across the enone; avoid prolonged exposure to light/heat.
Recommended PPE/practices (general):
Use in a fume hood with lab coat, safety glasses/goggles, and appropriate chemical-resistant gloves (e.g., nitrile). Avoid aerosol/dust generation.
First aid (general): rinse eyes/skin with water for 15 minutes if contacted; remove contaminated clothing; if inhaled, move to fresh air; if ingested, do not induce vomiting—seek medical attention. Follow SDS instructions.
Waste: Collect organic waste containing enones/phenols in halogen-free organic waste streams; follow institutional and regulatory disposal guidelines.
Solvent Selection
This compound is a para-hydroxylated aryl enone (phenolic α,β-unsaturated ketone). Solvent choices hinge on intended use (screening solutions vs. synthesis) and on balancing solubility with chemical stability.
Polarity/miscibility (general):
Expected to be sparingly soluble in water; readily soluble in DMSO and DMF; soluble to moderately soluble in acetone, acetonitrile, ethyl acetate, THF, and aromatic solvents; limited solubility in alkanes.
For biological screening stocks, anhydrous DMSO is commonly used; avoid prolonged storage in basic aqueous buffers which can promote addition reactions.
Considerations for stability:
The enone function can undergo base-catalyzed Michael additions and polymerization; minimize exposure to strong bases and nucleophile-rich media.
Phenolic OH can undergo oxidative darkening in air/light; inert atmosphere and amber vials are prudent.
Small comparison (general guidance):
DMSO: maximal solvating power; may react slowly with strong electrophiles at elevated T—room-temperature storage is usually acceptable; minimize moisture.
DMF/MeCN: good solvents for synthesis and analytics; DMF is higher-boiling for heated reactions.
EtOAc/THF: good for workups and chromatography; THF offers better polarity but be mindful of base-promoted side reactions.
When to choose alternatives:
For greener processing, consider 2-MeTHF or ethyl acetate where solubility permits (see Green Alternatives). For aqueous assays, use co-solvent strategies (e.g., 0.2–1% DMSO) and prepare fresh to limit degradation.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
General reconstitution and handling guidance (literature/practice; not item-specific specifications):
Solvents: Prepare stock solutions in dry, oxygen-poor solvents such as anhydrous DMSO or acetonitrile. For weighing solids, allow vial to equilibrate to room temperature in a desiccator to prevent moisture condensation.
Concentrations: Common screening stocks are 10–50 mM in DMSO. Verify solubility before preparing high-concentration stocks; warm gently if needed and vortex/sonicate to assist dissolution.
Aliquoting: Dispense into amber, airtight vials or 96/384-well plates under inert gas if possible to limit oxidation/polymerization; store at −20°C or below.
Freeze–thaw: Avoid repeated freeze–thaw cycles; use single-use aliquots. Inspect for precipitation, discoloration, or HPLC profile changes over time.
Aqueous use: Dilute into buffered media immediately before use; avoid strong bases and nucleophile-rich conditions which may consume the enone.
Stability notes (general):
Protect from light and air. The phenolic/enone system can slowly oxidize or undergo Michael additions during storage in reactive media. Review the batch CoA for any stability or inhibitor information specific to this lot.
Research Use Note: For research use only.
Structure & Identity
Brief description: 4-acryloylphenol (also written as 4-(prop-2-enoyl)phenol) is a para-hydroxylated aromatic bearing an α,β-unsaturated ketone (acryloyl) at the para position, making it a conjugated Michael acceptor.
Item-specific identifiers (from Product Data):
CAS: 95605-38-2
SKU: A607178
Grade: Moligand™
InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Literature identity data (for reference; not item-specific specifications):
Conjugation: extended π-system across the aryl–carbonyl–vinyl motif supports Michael-type reactivity and UV absorption.
Stereochemistry: none at sp3 centers; the vinylic double bond is terminal (no E/Z issue on the terminal CH2 end).
2D description in words: a benzene ring with a phenolic OH at one position and, para to it, a carbonyl group directly attached to the ring; the carbonyl is conjugated to a terminal vinyl group (–CO–CH=CH2).
1,4-Addition with C-, N-, S-nucleophiles to install β-substituents (e.g., malonate, nitromethane, thiols, secondary amines). Catalysts: tertiary amines, DBU, inorganic bases (K2CO3), or Lewis acids (ZnCl2, La(OTf)3) depending on nucleophile.
Selective hydrogenation: conjugate reduction to the saturated aryl ketone, or full reduction to the corresponding alcohol under stronger conditions (e.g., NaBH4 after hydrogenation).
Epoxidation of the double bond (e.g., mCPBA) followed by nucleophilic ring opening delivers β-functionalized carbonyls with stereocontrol options.
Phenol-centered transformations:
O-alkylation/arylation: Williamson ether synthesis (K2CO3, DMF/acetone) or Pd-catalyzed C–O coupling (Ullmann-type or Buchwald–Hartwig conditions with appropriate aryl halides) to tune electronics and solubility.
O-acylation: provides esters/carbonates for protecting-group strategies or pro-moieties.
Directed ortho-functionalization after transient protection can introduce additional handles for cross-coupling.
Convergence/retrosynthesis:
The enone can be constructed by acylation of 4-hydroxybenzene with acryloyl chloride (Friedel–Crafts acylation variants) or via oxidation/dehydration sequences from 4-hydroxypropiophenone analogs. Alternatively, Claisen–Schmidt-type condensations between 4-hydroxybenzaldehyde and acetaldehyde-derived synthons can access related frameworks.
Utility summary:
Rapid library build-outs around this core enable SAR exploration of electrophilicity, H-bonding via the phenol, and π–stacking interactions relevant to chemical biology and catalysis studies.
Target Specificity
Not applicable. This product is a small organic molecule and does not have antigen/epitope, clone, isotype, or species reactivity attributes. No target specificity data are provided in the Product Data.
Need help choosing the grade?
Our grade selection guide covers purity, stabilizer status, and application suitability for all variants in our catalog.
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