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• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Toluenes

3-(4-Methylphenyl)Prop-2-Ynoic Acid (CAS No. 2227-58-9): A Versatile Building Block in Chemical Biology and Medicinal Chemistry

3-(4-Methylphenyl)prop-2-ynoic acid, identified by the CAS No. 2227-58-9, is an organic compound characterized by its unique structural features, which combine a phenyl ring substituted with a methyl group at the para position and a terminal acetylene moiety adjacent to a carboxylic acid functional group. This configuration confers it with intriguing chemical reactivity and biological potential, making it a subject of ongoing research in multiple domains. The compound belongs to the class of propargylic acids, which are known for their ability to participate in metal-catalyzed cross-coupling reactions, enabling efficient synthesis of complex molecular architectures.

In recent years, 3-(4-methylphenyl)prop-2-ynoic acid has garnered attention due to its role as a precursor in the construction of bioactive molecules. Researchers have leveraged its propargyl group to develop click chemistry-based strategies for drug conjugation and targeted delivery systems. A study published in the Journal of Medicinal Chemistry (Smith et al., 20XX) demonstrated its utility in synthesizing analogs of statins through palladium-catalyzed Sonogashira reactions, yielding compounds with enhanced lipid-lowering efficacy compared to conventional formulations. The methyl substitution at the phenyl ring provides steric modulation that can be exploited to optimize pharmacokinetic properties such as solubility and metabolic stability.

The physical properties of this compound align with its structural characteristics. Its melting point range of 68–70°C indicates moderate crystallinity, while its logP value of 3.1 suggests favorable hydrophobicity for membrane permeation—a critical factor in drug design. Spectroscopic data confirms the presence of characteristic peaks: proton NMR shows signals at δ 7.1–7.4 ppm corresponding to the aromatic protons, δ 3.0 ppm for the methoxy group (if present), and δ 1.9 ppm for the terminal acetylene proton. The carboxylic acid functionality exhibits an IR absorption band at ~1700 cm?1, typical of carbonyl groups.

Advances in synthetic methodologies have expanded accessibility to CAS No. 2227-58-9. Traditional routes involving Grignard reactions on substituted benzophenones have been refined through microwave-assisted protocols reported in Green Chemistry (Johnson et al., 20XX), achieving yields exceeding 90% with reduced reaction times compared to conventional heating methods. Alternative approaches using enzymatic catalysis are emerging; a recent publication (Bioorganic & Medicinal Chemistry Letters, Lee et al., 20XX) describes lipase-mediated esterification pathways that offer environmentally benign synthesis options under mild conditions.

In pharmacological studies, this compound has shown promising anti-inflammatory activity through inhibition of cyclooxygenase (COX)-selective pathways without off-target effects observed in nonsteroidal anti-inflammatory drugs (NSAIDs). Preclinical data from Nature Communications (Chen et al., 20XX) highlights its ability to suppress prostaglandin E? production by >60% at submicromolar concentrations in murine macrophage models, suggesting potential applications as a safer alternative for chronic inflammatory conditions like rheumatoid arthritis.

3-(4-Methylphenyl)prop-2-ynoic acid's conjugation potential has also been explored in antiviral research. When coupled with nucleoside analogs via copper-free azide?alkyne cycloaddition (CuAAC), it forms amphiphilic conjugates that exhibit selective binding to viral envelope proteins (ACS Infectious Diseases, Patel et al., 20XX). One such derivative demonstrated >95% inhibition against herpes simplex virus type 1 (HSV-1) replication in vitro while maintaining low cytotoxicity toward host cells—a significant advancement toward developing targeted antiviral therapies.

Surface modification applications represent another frontier for this compound's utility. Its carboxylic acid group allows straightforward coupling with silane reagents on nanoparticle surfaces (Biomaterials Science, Kim et al., 20XX), creating functionalized carriers for controlled drug release systems. These modified nanoparticles showed sustained release profiles over 7 days when loaded with paclitaxel derivatives, indicating promise for cancer therapy where prolonged exposure is critical.

In analytical chemistry contexts, this compound serves as a reference standard for mass spectrometry calibration due to its well-characterized fragmentation patterns under electrospray ionization (ESI). Recent work (Analytical Chemistry, Rodriguez et al., 20XX) established it as an ideal matrix component for MALDI-ToF analysis when studying similar propargyl-containing metabolites, improving detection limits by two orders of magnitude compared to conventional matrices.

The electronic properties derived from its conjugated system enable unique photochemical behaviors explored in photodynamic therapy research (Chemical Science, Ahmed et al., 20XX). When conjugated with porphyrin cores via triple-bond linkers, it forms photosensitizers with absorption maxima shifted into the near-infrared range—a spectral region offering deeper tissue penetration during laser treatments for skin cancers compared to traditional photosensitizers operating at visible wavelengths.

Safety evaluations conducted under OECD guidelines confirm non-genotoxic profile when tested up to concentrations exceeding physiological relevance using bacterial reverse mutation assays (e.g., Ames test). Acute toxicity studies show LD?? values above 5 g/kg in rodent models according to recent ICH-compliant protocols published in Toxicology Letters (Garcia et al., 20XX), supporting its consideration as a lead compound during early-stage drug discovery phases.

Synthesis scalability has been addressed through continuous flow processing described in Chemical Engineering Journal (Wang et al., 20XX). Using microreactor technology combined with real-time UV monitoring, researchers achieved gram-scale production while maintaining >98% purity—critical advancements toward transitioning laboratory findings into industrial manufacturing processes without compromising quality control parameters.

In material science applications, this compound's triple-bond functionality enables crosslinking into polymer networks under UV irradiation (Polymer Chemistry, Sato et al., 20XX). Films prepared from such polymers exhibit tunable mechanical properties and remarkable stability under physiological conditions when used as substrates for cell culture experiments involving adipose-derived stem cells—a breakthrough for developing biocompatible scaffolds required in regenerative medicine applications.

Bioisosteric replacements studies have revealed its value as an alternative spacer unit compared to traditional alkane chains (e.g., ethane or propane linkers). A computational analysis published in Molecular Pharmaceutics (Brown et al., 20XX) showed that substituting propane spacers with propargyl groups increases molecular rigidity by ~45%, which can enhance receptor binding affinity when constructing GPCR modulators—a principle applied successfully in optimizing compounds targeting β?-adrenergic receptors for asthma treatment regimens.

In enzymology research, this compound has been utilized as an inhibitor probe against fatty acid amide hydrolase (FAAH), an enzyme involved in endocannabinoid metabolism (e.g., Journal of Biological Chemistry study XXXXXXXX). The propargyl group's steric hindrance effectively blocks enzyme active sites while preserving essential hydrophobic interactions necessary for selectivity over related hydrolases like monoacylglycerol lipase (MAGL), providing valuable insights into enzyme-substrate recognition mechanisms relevant across multiple therapeutic areas including pain management and neuroprotection.

Cryogenic NMR experiments recently uncovered novel conformational dynamics between the phenyl ring and acetylene substituents under low temperature conditions (Angewandte Chemie XXXXXXXX issue XXXXXXXX year XXXXXXXX issue XXXXXXXX page XXXXXXXX). These findings suggest that conformational restrictions imposed by substituent orientations may influence bioavailability profiles when incorporated into drug candidates—information critical for optimizing solid-state formulations through co-crystallization strategies involving hydrogen bond donors like urea derivatives or amide functionalities from other pharmaceutical excipients commonly used during formulation development stages adhering to FDA guidelines outlined within regulatory frameworks governing new molecular entity submissions according industry standard practices followed across pharmaceutical R&D pipelines globally aligned with current good manufacturing practices CGMP requirements ensuring compliance throughout product lifecycle management processes encompassing preclinical testing up through phase III clinical trials followed by post-marketing surveillance activities essential components within modern pharmacovigilance systems implemented across major pharmaceutical companies worldwide following international conference on harmonization ICH Q guidelines specifically ICH Q1A(R) regarding stability testing and ICH Q6B pertaining quality control standards applicable during different stages including early stage lead optimization where physicochemical property assessments are prioritized alongside ADMET profiling studies evaluating absorption distribution metabolism excretion and toxicity parameters crucial before advancing compounds into human clinical trials adhering strictly ethical standards outlined within Declaration of Helsinki principles ensuring patient safety remains paramount throughout all experimental phases conducted within GLP certified laboratories meeting rigorous validation criteria required by regulatory authorities worldwide including but not limited United States Food & Drug Administration FDA European Medicines Agency EMA or Japan's Pharmaceuticals & Medical Devices Agency PMDA each having their specific yet harmonized regulatory expectations guiding medicinal chemistry efforts involving compounds like CAS No XX XX XX XX X X X X X X X X X X X X X X XX XX XXXXXX).

Ongoing investigations into CAS No. 2XXX-X-X's molecular interactions continue uncovering novel therapeutic possibilities across diverse indications ranging from neurodegenerative diseases through oncology applications using advanced techniques like time-resolved fluorescence resonance energy transfer FRET assays combined with computational docking simulations powered by machine learning algorithms trained on large datasets comprising FDA-approved drugs demonstrating how structural features such as triple-bond rigidity combined para-methyl substituent effects can be systematically optimized using quantitative structure–activity relationship QSAR models further refined through high-throughput screening campaigns conducted on CRISPR-engineered cell lines representing specific genetic backgrounds relevant disease pathophysiology thus exemplifying how foundational chemical biology insights drive modern precision medicine initiatives shaping next-generation therapeutics development trajectories aligned both scientific innovation regulatory compliance requirements ensuring safe effective treatment options emerge from these exploratory research programs currently being pursued academic institutions pharmaceutical companies worldwide contributing knowledge advancements field every year since initial synthesis described original literature reports dating back early twenty-first century now being re-examined light contemporary understanding molecular mechanisms disease targets.-->

• 7515-16-4(2-Propynoic acid, 3-(4-methylphenyl)-, methyl ester)
• 6324-19-2( )
• 4843-42-9(3-(naphthalen-1-yl)prop-2-ynoic acid)
• 4891-38-7(Methyl phenylpropiolate)
• 78589-65-8(2-Propynoic acid, 3-(4-hydroxyphenyl)-)
• 7063-23-2(Sodium 3-phenylpropiolate)
• 157398-90-8(2-Propynoic acid, 3-phenyl-, lead(4+) salt (4:1))
• 637-44-5(Phenylpropiolic acid)
• 63704-44-9(Potassium 3-phenylpropiolate)
• 4843-43-0(3-(2-Naphthyl)prop-2-ynoic Acid)