This compound belongs to the class of organic compounds known as aryl-phenylketones. These are aromatic compounds containing a ketone substituted by one aryl group, and a phenyl group.
External Descriptors
Not available
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.
Certificati (CoA, COO, BSE/TSE e tabella di analisi)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Proprietà chimiche e fisiche
Peso molecolare
283.320 g/mol
XLogP3
2.600
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
5
Exact Mass
283.121 Da
Monoisotopic Mass
283.121 Da
Topological Polar Surface Area
48.300 Ų
Heavy Atom Count
21
Formal Charge
0
Complexity
403.000
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
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Recensioni
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Application Protocols
No item-specific tested applications or dilution protocols are provided for this product. As a small-molecule research chemical, typical handling includes:
Stock solution preparation (general guidance): Dissolve in dry DMSO or ethanol to prepare concentrated stocks (e.g., 10–100 mM), then dilute into assay or reaction media while monitoring for precipitation and ester stability.
Analytical characterization: Confirm identity/purity by NMR, LC–MS, and HPLC before critical use. For hydrolysis studies, establish time-course profiles in your medium of interest.
For procedural details tailored to your experiment (e.g., hydrolysis kinetics, coupling to amines), refer to the Reaction Conditions and Synthetic Utility sections and adjust based on pilot experiments.
Biological Roles
Item-specific biological data: Not specified for this item; refer to CoA/Spec Sheet. The following is general, literature-based context and not a medical claim.
Ketorolac (parent acid) is widely studied in biochemistry as a cyclooxygenase (COX) enzyme inhibitor. The ethyl ester is a masked/carboxyl-protected form and is typically expected to have reduced direct COX binding until hydrolyzed to the acid in vitro or in situ.
Utility in assays: The ester can be used as a permeability surrogate or pro-moiety in cell-free or cell-based research where controlled esterase-mediated conversion to the active acid is of interest. Hydrolysis rates will depend on the enzyme source (non-specific esterases) and medium conditions.
Stereochemistry consideration: Studies often note enantioselective interactions of ketorolac with enzyme targets; the ester maintains the stereocenter and may undergo enantioselective hydrolysis depending on the biocatalyst.
Off-target profiling (general): Aromatic heterocycles with aryl ketones can engage in π–π and H-bond interactions; the ester reduces acidity, potentially modifying distribution and nonspecific binding in membranes versus the acid.
Important: This product is designated For research use only and is not intended for use in humans or for diagnostic purposes.
Buffer Applications
This compound is a neutral organic ethyl ester and is not commonly used to prepare aqueous buffer systems. If used in biochemical experiments, it is typically dissolved in an organic co-solvent (e.g., DMSO or ethanol) and then diluted into buffered media.
For studies requiring the parent acid’s behavior in buffers, perform controlled hydrolysis to ketorolac acid and then adjust pH using standard buffering systems (e.g., phosphate, HEPES) appropriate to the target pH range.
No item-specific buffer formulations are provided for this product.
Green Alternatives
While the compound itself is fixed, greener choices can be made for its use and transformations:
Greener solvent choices (literature-based):
For ester hydrolysis: prefer aqueous ethanol or methanol with catalytic/base conditions over chlorinated solvents. Water-rich media can reduce organic solvent volumes.
For workups/extractions: consider ethyl acetate or 2-methyltetrahydrofuran (2-MeTHF) instead of DCM.
For recrystallization/purification: attempt EtOAc/hexanes or IPA/ethyl acetate before resorting to chlorinated systems.
Comparison (general):
DCM/chloroform: excellent solvency, but higher environmental/health impact.
Ethyl acetate/IPA/2-MeTHF: lower toxicity and better EHS profiles; sometimes require slightly higher volumes or longer times to achieve equivalent dissolution.
Process-intensification ideas:
Enzymatic hydrolysis (lipases) in aqueous-organic biphasic systems can offer milder, selective conversion of the ethyl ester to the acid with lower E-factors.
Microwave-assisted saponification in aqueous ethanol can reduce time and energy use.
Waste minimization:
Use telescoped sequences (e.g., hydrolysis → in situ acid–amide coupling) to reduce isolation steps and solvent waste where purity specs allow.
Note: Validate solvent compatibility with your specific downstream analytics and safety requirements.
Pharmaceutical Uses
No pharmacopeial status, excipient role, or formulation specifications are provided for this item; refer to CoA/Spec Sheet.
General R&D context (non-clinical, literature-based):
Pro-moiety/intermediate: The ethyl ester of ketorolac can serve as a synthetic intermediate in medicinal chemistry workflows to access salts, amides, or other derivatives of the parent acid after deprotection.
Preformulation studies: Researchers sometimes evaluate ester vs. acid forms to compare solubility, permeability, and stability in model systems, without implying therapeutic use.
Analytical standards (research only): The ester may be used as a reference or process control material in synthetic route development.
Important restriction: This product is provided for research use only and is not an API, excipient, or for human/animal administration.
Physical Properties
Item-specific specifications:
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.
Molecular Formula: Not specified for this item; refer to CoA/Spec Sheet.
Melting/Boiling Point, Density, Refractive Index: Not specified for this item; refer to CoA/Spec Sheet.
Water content, residual solvents, metal content, UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.
General/literature guidance for ethyl esters of aryl heterocycles (not item-specific):
Solubility (literature): Typically sparingly soluble in water and readily soluble in common organic solvents (e.g., dichloromethane, ethyl acetate, acetone, toluene, alcohols), with good solubility in polar aprotic media (DMF, DMSO).
LogP (qualitative, literature): Esterification generally increases hydrophobicity vs. the corresponding acid; expect moderate to high lipophilicity relative to ketorolac acid.
pKa (functional behavior): The ester is not acidic at the carboxyl carbon (no carboxyl proton); acid–base behavior is dominated by heteroaromatic nitrogen (weakly basic at best). Hydrolyzes to the acid under strong acidic or basic conditions.
Note: For exact numeric physical constants of this specific item, consult the product CoA/Spec Sheet or SDS.
Quality and Grades
Item-specific quality information:
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/Inhibitors: Not specified for this item; refer to CoA/Spec Sheet.
Guidance on grades (general):
In the absence of a stated grade (e.g., AR, HPLC, USP, or synthesis grade), assume the material is intended for research and development applications. For analytical or regulated uses, require a Certificate of Analysis (CoA) detailing assay, impurities, and relevant chromatographic purity.
For chromatography-sensitive work (e.g., photometric detection), an HPLC grade specification often ensures lower UV background and minimal non-volatile residues; verify if such control is required by your method.
If stabilizers are present in some lots (common for hydrolytically labile esters), they will be declared on the CoA/Spec Sheet. The presence/absence of stabilizers can impact reactivity (e.g., trace acid/base scavengers) and analytical baselines.
Recommendation:
Request the current CoA for batch-specific assay, residual solvents, water content (Karl Fischer), and chromatographic purity prior to use in critical synthesis or bioanalytical method development.
Reaction and Applications
Manufacturer Applications: Not specified in Product Data beyond research use. The following expands typical uses of ethyl esters of aryl heterocycles (literature-based):
Protected acid handle: The ethyl ester serves as a carboxyl-protecting group for ketorolac, enabling transformations that would be incompatible with the free acid (e.g., acylations on other positions, neutral-condition coupling screens) without salt formation or acid-base complications.
Hydrolysis to ketorolac acid: Controlled saponification (e.g., NaOH or K2CO3 in MeOH/H2O or THF/H2O) yields ketorolac (free acid), a valuable intermediate for further derivatization (amide formation, salt formation for materials studies, etc.). Acidic hydrolysis (aq. HCl, reflux) is also possible but may affect acid-sensitive motifs.
Transesterification: Under acid catalysis (H2SO4, p-TsOH) or metal-catalyzed conditions, the ethyl ester can be exchanged to other alcohols (e.g., isopropyl, benzyl) to tune properties or introduce a removable protecting group (e.g., benzyl for hydrogenolysis).
Amide synthesis via two-step: Hydrolyze to the acid, then couple with amines using carbodiimides (EDC/HOBt, DIC/HOAt) or uronium reagents (HATU, TBTU) under mild base (DIPEA). Direct aminolysis of aryl ethyl esters is generally sluggish; the acid route is recommended.
Reductions (caution): Strong hydride donors (LiAlH4) reduce esters to primary alcohols, which fundamentally alters the ketorolac scaffold; use only if such derivatives are desired for SAR or materials studies.
Practical tips:
Maintain anhydrous organic media when ester integrity is required. Avoid strong base during chromatography (use neutral/alumina if needed). Monitor reactions by LC–MS or HPLC (ester vs. acid retention difference is diagnostic).
Reaction Conditions
Item-specific reaction parameters are not provided. The following are general, literature-based guidelines for transformations of ethyl esters similar to ketorolac ethyl ester:
Base-catalyzed hydrolysis (saponification):
Solvent: MeOH/H2O or EtOH/H2O (1:1 to 9:1 v/v).
Base: NaOH or KOH (1.0–2.0 equiv relative to ester).
Temperature: 20–60 °C (often complete within 0.5–6 h depending on structure/solvent ratio).
Workup: Quench with dilute acid to pH 2–3, extract as needed.
Acidic hydrolysis:
Reagent: aq. HCl (1–3 M) or H2SO4; co-solvent: dioxane, THF, or EtOH.
Temperature: reflux may be required for robust esters; monitor for ketone stability.
Transesterification (acid-catalyzed):
Catalyst: p-TsOH (1–10 mol%).
Solvent/nucleophile: excess ROH; azeotropic water removal (Dean–Stark) or 3 Å MS.
Temperature: 50–110 °C depending on alcohol.
Amide formation (via acid after hydrolysis):
Activators: EDC/HOBt, HATU, or T3P.
Base: DIPEA or NMM.
Solvent: DMF, DCM, or NMP.
Temperature: 0–25 °C to maintain chemoselectivity.
Analytical monitoring: RP-HPLC with ACN/H2O (0.1% formic acid) or LC–MS is effective to distinguish ester vs. acid.
Always optimize conditions for the specific substrate and consult primary literature when scaling.
Safety and Handling
Item-specific hazard information:
GHS Classification / Pictograms / Signal Word / H-Statements: Not specified for this item; refer to SDS.
General handling guidance (professional laboratory practice; defer to SDS for authoritative details):
PPE: Wear lab coat, safety glasses or face shield, and suitable gloves (e.g., nitrile). Use in a fume hood to avoid inhalation of dusts/vapors/aerosols.
Incompatibilities: Avoid strong acids or bases and prolonged exposure to moisture when ester integrity must be maintained; these conditions promote hydrolysis to the acid. Keep away from strong oxidizers.
Thermal stability: Organic esters may decompose upon strong heating; avoid unnecessary thermal stress. Follow any temperature guidance on the label.
First-aid (overview): If skin contact occurs, wash with plenty of water/soap. If eye contact, rinse cautiously with water for several minutes and seek medical advice. If inhaled, move to fresh air. If ingested, rinse mouth; do not induce vomiting; seek medical attention. Always consult the SDS for specifics.
Spill response: Absorb small spills with inert material (vermiculite, silica) and collect for disposal. Prevent release to drains. Ventilate area.
Waste: Dispose according to institutional and local regulations for organic laboratory chemicals.
Note: This product is designated For research use only per Product Data.
Solvent Selection
Item-specific solubility/solvent specs: Not specified for this item; refer to CoA/Spec Sheet.
General solvent guidance for aryl-heterocyclic ethyl esters (literature-based):
Polarity/miscibility: Typically nonpolar to moderately polar; soluble in common organic solvents such as DCM, chloroform, EtOAc, acetone, THF, toluene, ethanol, isopropanol, and polar aprotics (DMF, DMSO). Low aqueous solubility is expected relative to the corresponding carboxylic acid.
Chromatography: Normal-phase silica or reversed-phase C18 (with acetonitrile/water or methanol/water) can be used. Esters often elute later than acids in RP due to higher hydrophobicity.
Workup considerations: If hydrolysis to ketorolac acid is undesired, avoid prolonged contact with basic aqueous washes. For base-sensitive handling, use neutral brine washes and dry organic layers promptly over MgSO4 or Na2SO4.
Selection tips:
For reactions sensitive to nucleophiles, favor DCM, toluene, or acetonitrile over alcohols.
For hydrolysis/saponification (to regenerate ketorolac acid), MeOH/H2O or EtOH/H2O with base is typical.
For stock solutions for screening, DMSO affords high solubility; dilute into assay buffer or organic eluent as needed.
Always verify actual solubility experimentally for your lot and application.
Storage and Reconstitution
Item-specific storage/shipping:
Storage Conditions: Room temperature (per Product Data). Avoid humid environments.
Shipped In: Not specified for this item; refer to CoA/Spec Sheet.
General best practices for this class of compounds:
Container/atmosphere: Store tightly sealed in an inert atmosphere (e.g., under nitrogen) if possible, especially for long-term storage, to minimize hydrolysis from atmospheric moisture.
Light/moisture protection: Keep in a dry cabinet or with desiccant; protect from prolonged light exposure.
Stability: Esters can slowly hydrolyze in the presence of moisture or base; re-check purity by HPLC/LC–MS periodically if stored for extended periods.
Reconstitution and solution handling (general guidance):
Dissolve in anhydrous solvents (e.g., DMSO, DMF, dry EtOH, dry DCM) immediately before use.
Working solutions: For biological assays, prepare DMSO or ethanol stocks and dilute into buffer with vigorous mixing; maintain final organic content at levels compatible with your system.
Freeze–thaw: If solutions must be stored, aliquot and freeze at −20 °C to avoid repeated freeze–thaw cycles; verify stability upon thawing.
Always refer to the product CoA/Spec Sheet and SDS for authoritative storage and handling guidance.
Core scaffold: Ketorolac is a 5-benzoyl-2,3-dihydro-1H-pyrrolizine derivative. The ethyl ester is the ethylated form of the carboxylic acid at the 1-position, converting the acid to an ethyl carboxylate.
Functional groups: An aryl ketone (benzoyl substituent on the heterobicycle) and an alkyl ester (–CO2Et). The molecule is aromatic/heteroaromatic with a fused bicyclic pyrrolizine ring system.
Stereochemistry: Ketorolac is typically handled as a racemate (one stereocenter in the bicyclic core). The ethyl ester preserves the same stereocenter as the parent acid.
2D structure (in words): A fused five–five bicyclic nitrogen-containing ring (pyrrolizine) bearing at C-5 a benzoyl group (–CO–C6H5) and at N-1/C-1 the carboxylate moiety in the ethyl ester form (–CO2CH2CH3).
Synthetic Utility
Key functional elements (general, literature-based):
Ethyl ester at the carboxyl position: functions as a protecting group and handle for downstream transformations (hydrolysis → acid; transesterification; formation of activated esters; or conversion to amides via the acid).
Aryl ketone (benzoyl substituent): electrophilic at the carbonyl; can participate in selective reductions (e.g., NaBH4 to secondary alcohol, if desired for analogs), oxime/hydrazone formation for derivatization, or serve as a spectroscopic handle.
Pyrrolizine core (fused N-heterocycle): Offers a rigid, π-rich scaffold; typically stable to moderate bases and nucleophiles under conditions that preserve the ester.
Representative synthetic maneuvers:
Saponification: EtOH/H2O, NaOH (1–2 equiv), 0–25 °C to reflux; then acidify to isolate ketorolac acid.
Activation/coupling (via acid): Convert the acid to amides with EDC/HOBt or HATU/DIPEA in DMF or DCM; or form acid chlorides with oxalyl chloride (catalytic DMF) when compatible.
Transesterification: p-TsOH (cat.) in ROH under Dean–Stark or molecular sieves; or use metal alkoxides (e.g., NaOMe) with caution due to potential hydrolysis/side reactions.
Selective ketone derivatization: Formation of oximes/hydrazones (NH2OH, hydrazines) for analytical tagging or protection, reversible under acidic conditions.
Notes:
Control moisture and pH to avoid unintended ester cleavage. Monitor by LC–MS (acid vs. ester masses/retention).
Target Specificity
Not applicable to this product category. This item is a small-molecule ester, not an antibody, enzyme, or targeted biologic. No antigen, epitope, clone, or isotype information applies.
For biochemical work, consult the Biological Roles section for general literature context regarding the ketorolac scaffold.
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