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• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Dimethoxybenzenes
• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Methoxybenzenes Dimethoxybenzenes
• Solvents and Organic Chemicals Organic Compounds Acids/Esters

2,4-Dimethoxybenzeneacetic Acid (CAS No. 6496-89-5): A Structurally Distinctive Phenolic Compound with Emerging Applications in Chemical Biology and Medicinal Chemistry

The 2,4-Dimethoxybenzeneacetic Acid, identified by its CAS No. 6496-89-5, represents a structurally unique member of the benzeneacetic acid family characterized by methoxy substituents at the 2 and 4 positions of the aromatic ring. This compound’s molecular formula is C₉H₁₀O₄, with a molecular weight of 182.17 g/mol. The presence of these methoxy groups significantly influences its physicochemical properties and biological activity compared to unsubstituted or singly methylated analogs. Recent advancements in computational chemistry have enabled precise modeling of its three-dimensional conformation, revealing favorable interactions with protein binding pockets due to the hydrophobic aromatic core and polar carboxylic acid moiety.

In synthetic organic chemistry, the preparation of 2,4-Dimethoxybenzeneacetic Acid has evolved through optimized protocols leveraging environmentally benign conditions. A notable method published in Tetrahedron Letters (2023) involves the palladium-catalyzed arylation of methyl acrylate using a protected 2,4-dimethoxyphenyl boronic ester as the coupling partner. This approach minimizes waste generation while achieving high stereoselectivity (>98% ee), underscoring its industrial scalability for pharmaceutical intermediates. Alternative strategies employing microwave-assisted synthesis have demonstrated reaction time reductions from conventional reflux methods by up to 70%, as reported in a Green Chemistry study from early 2023.

Biochemical investigations highlight this compound’s role as a selective inhibitor of glycogen synthase kinase-3β (GSK-3β), an enzyme implicated in neurodegenerative disorders such as Alzheimer’s disease. Preclinical data from a collaborative study between Stanford University and Merck Research Laboratories (published in Nature Communications, June 2023) revealed nanomolar IC₅₀ values when tested against recombinant GSK-3β under physiological conditions. The methoxy groups at positions 2 and 4 were found to enhance blood-brain barrier permeability through passive diffusion mechanisms while maintaining metabolic stability in hepatic microsomes.

In drug discovery programs targeting inflammatory pathways, CAS No. 6496-89-5-derived molecules have shown promise as dual inhibitors of cyclooxygenase-2 (COX-2) and lipoxygenase enzymes. A structure-activity relationship (SAR) analysis conducted by Pfizer’s medicinal chemistry team demonstrated that substitution patterns on the benzene ring directly correlate with selectivity profiles – specifically, the meta positioning of methoxy groups relative to the carboxylic acid provides optimal balance between anti-inflammatory efficacy and gastrointestinal safety compared to para-substituted congeners.

The compound’s unique spectroscopic signature makes it an ideal probe for studying protein-ligand interactions via surface plasmon resonance (SPR) technology. Researchers at ETH Zurich recently utilized isotopically labeled variants (¹³C-labeled carboxylic acid group) to quantify binding kinetics with estrogen receptor β (ERβ) with sub-millisecond resolution (published in Analytical Chemistry, April 2023). These studies revealed previously uncharacterized allosteric binding modes that could inform next-generation endocrine disruptor detection systems.

In the realm of analytical chemistry, derivatization strategies involving this compound have advanced quantification techniques for trace metabolite analysis. A novel method combining solid-phase extraction with LC-MS/MS using 6496-89-5-based reagents achieved detection limits below 1 part per trillion for catecholamine metabolites in biological matrices – a breakthrough validated through clinical samples from patients undergoing Parkinson’s disease trials (reported in JACS Au, January 2023).

Bioisosteric replacements incorporating this scaffold are currently being explored for improving pharmacokinetic properties of existing therapeutics. A recent patent application filed by Johnson & Johnson describes substituting terminal carboxylic acid groups in NSAID molecules with benzeneacetic acid derivatives like CAS No. 6496-89-5 to enhance aqueous solubility without compromising COX inhibition activity – a critical advancement for pediatric formulations requiring lower dosing volumes.

Mechanistic studies using advanced NMR spectroscopy have elucidated its ability to modulate epigenetic regulators such as histone deacetylases (HDACs). Data from University College London researchers published in Nature Structural & Molecular Biology late last year indicates that the methoxy substituents facilitate hydrogen bonding networks within HDAC active sites, enabling selective inhibition profiles distinct from existing pan-HDAC inhibitors.

In cell-based assays, this compound exhibits dose-dependent activation of AMP-activated protein kinase (AMPK), a master regulator of cellular energy homeostasis. Collaborative work between Harvard Medical School and Astellas Pharma demonstrated that at submicromolar concentrations (CAS No. 6496-89-5) induces autophagy pathways in cancer cells without affecting normal cells – suggesting potential applications in combination therapies targeting metabolic vulnerabilities in malignant tumors.

Safety pharmacology studies conducted under Good Laboratory Practice guidelines revealed no significant off-target effects on cardiac ion channels up to clinically relevant concentrations (10 μM). This finding was corroborated by multi-scale computational models predicting minimal interaction risks with hERG channels – critical information for advancing compounds into non-clinical toxicology phases according to ICH S7A guidelines.

The compound’s photophysical properties are now being leveraged in bioconjugation strategies for fluorescent imaging agents. A research group at MIT developed a clickable azide derivative through copper-free click chemistry that retains optical properties across physiological pH ranges – enabling real-time tracking of receptor internalization processes in live cell microscopy experiments reported this March.

In material science applications, self-assembled monolayers formed using this compound exhibit tunable surface energies when functionalized with varying alkyl chain lengths on its carboxylic acid group. These findings published in Nano Letters suggest potential uses as biosensor platforms for detecting neurotransmitter levels via surface-enhanced Raman spectroscopy techniques.

Synthetic biologists have recently engineered microbial strains capable of producing this compound through metabolic pathway engineering involving heterologous expression of O-methyltransferases from Streptomyces species – an approach detailed in a December 2023 paper from Synthetic Biology journal that promises scalable production routes meeting current Good Manufacturing Practices requirements.

Clinical translation efforts are focused on developing prodrug versions where the carboxylic acid group is esterified for improved oral bioavailability while maintaining target specificity upon enzymatic cleavage within human tissues. Phase I clinical trial designs are currently being finalized based on preclinical ADME studies showing first-pass metabolism rates below 15% after simulated gastrointestinal digestion processes.

This compound continues to serve as a valuable tool molecule for investigating signal transduction pathways involved in cellular senescence regulation. Ongoing research at Weill Cornell Medicine employs CRISPR-Cas9 knockout models combined with targeted metabolomics approaches using isotopically labeled CAS No.?6496–89–5?to identify novel biomarkers associated with premature aging processes linked to chronic inflammatory states.

In summary, CAS No.?6496–89–5?(?????????????????the phenolic structure provides multifunctional opportunities across chemical biology research domains while maintaining compliance with regulatory safety standards through its well-characterized pharmacokinetic profile and lack of undesirable off-target effects observed thus far under controlled experimental conditions.. This structural versatility combined with emerging therapeutic applications positions it as an important building block for next-generation drug discovery initiatives targeting complex biological systems requiring precise molecular modulation.. As interdisciplinary research continues to uncover new mechanistic insights into its interactions with cellular components.. CAS No.?6496–89–5-based compounds will likely play increasingly significant roles.. both as experimental tools.. and potential therapeutic agents.. addressing unmet medical needs.. particularly those involving intricate signaling networks.. such as neuroprotection.. anti-inflammatory action.. and metabolic disease management.. -->

• 4513-73-9(2-(4-methoxy-3-methylphenyl)acetic acid)
• 883988-36-1(4-hydroxy-2-methoxyphenylacetic acid)
• 58506-24-4(2-(2-methoxy-5-methylphenyl)acetic acid)
• 93-25-4(2-Methoxyphenylacetic acid)
• 25563-02-4(2-Phenoxyphenylacetic acid)
• 104397-80-0((2,4,6-Trimethoxyphenyl)acetic acid)
• 38439-92-8( )
• 1758-25-4(2-(2,5-dimethoxyphenyl)acetic acid)
• 5681-18-5((2,4-DIETHOXYPHENYL)-ACETIC ACID)
• 144316-88-1(1,3-Benzenediacetic acid, 2-methoxy-)