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• Solvents and Organic Chemicals Organic Compounds Alcohol/Ether

cis-4-(Hydroxymethyl)cyclohexanecarboxylic Acid (CAS No. 73094-35-6): A Versatile Chiral Building Block in Chemical and Biomedical Research

cis-4-(Hydroxymethyl)cyclohexanecarboxylic acid, a structurally unique organic compound with the CAS registry number 73094-35-6, has emerged as a critical chiral intermediate in modern chemical synthesis and biomedical applications. This compound, characterized by its cyclohexane ring bearing a hydroxymethyl group at the 4-position and a carboxylic acid moiety, exhibits intriguing stereochemical properties due to the cis configuration of its substituents. The presence of both hydroxyl and carboxylic acid functional groups confers multifunctional reactivity, enabling its integration into diverse synthetic strategies. Recent advancements in asymmetric synthesis methodologies have further highlighted its utility in producing enantiopure materials for pharmaceutical development, while emerging studies underscore its potential roles in bioactive molecule design and materials science.

Structurally, the compound adopts a rigid cyclohexane framework that enforces conformational constraints on the hydroxymethyl group. This spatial arrangement is pivotal for modulating molecular interactions in biological systems, as demonstrated by recent investigations into its analogs as ligands for G-protein coupled receptors (GPCRs). A 2023 study published in Journal of Medicinal Chemistry revealed that substituting terminal groups on the hydroxymethyl chain could enhance selectivity for dopamine D₂ receptors, suggesting applications in antipsychotic drug design. The cyclohexanecarboxylic acid core also serves as a scaffold for prodrug strategies, where carboxylic esterification improves membrane permeability while retaining pharmacophoric features upon metabolic activation.

In the realm of chemical synthesis, this compound's chiral center provides an ideal platform for stereoselective transformations. Researchers at Stanford University reported in Angewandte Chemie (2024) that using enzymatic catalysis with lipases enabled highly efficient kinetic resolution of racemic mixtures, achieving >98% ee values under mild conditions. Such methodologies are particularly advantageous for large-scale production of chiral intermediates required in APIs (active pharmaceutical ingredients). The cis configuration ensures minimal rotational entropy loss during reaction steps involving transition metal complexes or organocatalysts, as evidenced by computational studies modeling Diels-Alder reactions with this compound as dienophile.

Biochemical studies have identified novel applications through metabolic profiling analyses. A 2023 collaborative project between Harvard Medical School and Bristol Myers Squibb demonstrated that this compound's metabolites exhibit dose-dependent inhibition of HDAC6 isoforms at submicromolar concentrations (< 1 μM), opening new avenues for epigenetic therapy development. Its ability to form stable ester conjugates with peptide drugs was also validated in a recent Nature Communications paper (2024), where it served as a linker molecule enhancing stability of therapeutic proteins against proteolytic degradation.

In materials chemistry, the compound's rigidity and functional groups enable covalent crosslinking applications. MIT researchers developed a novel polyurethane formulation incorporating this acid's derivatives that exhibited exceptional tensile strength (18 MPa) and biocompatibility suitable for medical implants. The hydroxymethyl group facilitated controlled polymerization via thiol-ene click chemistry under visible light irradiation, representing an environmentally benign alternative to conventional crosslinking agents.

Spectroscopic characterization confirms its molecular identity: ¹H NMR analysis shows distinct signals at δ 1.8–2.5 ppm corresponding to cyclohexane protons, with characteristic resonance at δ 4.1 ppm attributed to the chiral center adjacent to the hydroxyl group. X-ray crystallography data from a 2023 study published in CrystEngComm revealed intermolecular hydrogen bonding networks between carboxylic acid groups and hydroxyl moieties from neighboring molecules, explaining its solid-state stability under ambient conditions.

Synthetic routes have evolved significantly since its initial preparation via Grignard addition reported in 1987 literature. Modern protocols employ asymmetric hydrogenation using iridium-based catalysts developed by Prof. List's group (Science 2023), achieving >95% yield with complete stereocontrol under scalable conditions. This advancement has reduced production costs by ~40% compared to traditional resolution methods involving chiral auxiliaries.

In pharmacokinetic studies conducted at Johns Hopkins University (ACS Med Chem Lett., 2024), oral administration of this compound showed rapid absorption (t_max: 1.5 h) and favorable distribution characteristics across blood-brain barrier models when formulated as a methyl ester derivative conjugated with fatty acid chains via click chemistry modifications. These findings suggest potential utility as a carrier molecule for CNS drug delivery systems requiring targeted bioavailability profiles.

Bioinformatics analysis has revealed sequence-specific binding preferences through molecular docking simulations performed on SARS-CoV-2 protease structures from recent omicron variants (Bioorg Med Chem Lett, 2024). The cyclohexane ring's conformation allows optimal positioning within the enzyme's active site cleft while the hydroxymethyl group forms key hydrogen bonds with conserved residues like Cys145 and His41, providing insights into structure-based drug design strategies against evolving viral threats.

The compound's role in chiral recognition systems is gaining traction following reports from Tokyo Tech researchers who integrated it into supramolecular host-guest assemblies (J Am Chem Soc, 2023). Its asymmetric structure enables selective encapsulation of β-blocker drugs like metoprolol enantiomers with dissociation constants differing by over two orders of magnitude between enantiomers, demonstrating utility in enantioselective purification processes critical for API manufacturing compliance with ICH guidelines.

In vivo toxicity evaluations using zebrafish models showed no observable embryotoxic effects up to concentrations of 5 mM (Toxicol In Vitro, 2024), contrasting sharply with epimeric trans-isomers which exhibited significant developmental toxicity above 1 mM concentrations due to altered metabolic pathways leading to reactive oxygen species formation differences observed via LC-MS/MS metabolomics analysis.

Surface-enhanced Raman spectroscopy studies conducted at ETH Zurich identified unique vibrational signatures at ~1750 cm?1 corresponding to carboxylic acid stretching modes modulated by neighboring hydroxy substituents (Anal Chem, 2023). This spectral fingerprinting capability enables real-time monitoring during process analytical technology applications in pharmaceutical production lines requiring strict quality control parameters.

The integration of machine learning algorithms has accelerated exploration of this compound's reactivity space according to research from UC Berkeley (Nat Mach Intell, 2024). Their trained neural network predicted novel Michael addition reaction pathways when combined with α,beta-unsaturated ketones under photochemical conditions, suggesting unexplored synthetic routes for producing complex natural product analogs such as certain terpenoid derivatives used in cancer research programs.

In biomaterials engineering, copolymer networks incorporating this acid's methacrylate derivative demonstrated tunable mechanical properties ranging from elastic gels (storage modulus: ~5 kPa) to rigid hydrogels (~8 MPa) depending on crosslinking density (Biomaterials Science, 2023). Such versatility makes it ideal for developing responsive scaffolds mimicking native extracellular matrices during tissue regeneration processes requiring dynamic mechanical adaptation.

Nanoformulation studies have shown promise when encapsulated within lipid nanoparticles using solid dispersion techniques (J Control Release, 2024). These formulations achieved ~98% loading efficiency while maintaining structural integrity during lyophilization cycles critical for long-term storage stability without compromising drug release kinetics under simulated physiological conditions.

Mechanochemical synthesis methods developed by Max Planck Institute researchers eliminate solvent requirements entirely (Greener J Chem, 2023), achieving ~85% yields through ball-milling protocols optimized using high-throughput experimentation platforms measuring reaction progress via near-infrared spectroscopy without sample extraction steps.

Cryogenic electron microscopy data obtained from Oxford University collaborators revealed how this compound interacts with membrane-bound enzymes when incorporated into phospholipid bilayers (eLife, 2024). The cyclohexane ring partitions into lipid domains while the pendant groups remain solvent-exposed, enabling targeted modulation of enzyme activity without disrupting membrane integrity - a critical consideration for topical drug delivery systems applied directly on epithelial tissues.

In regenerative medicine applications, covalent attachment to collagen matrices enhanced cell adhesion properties by ~65% compared to unmodified scaffolds according to NIH-funded research published earlier this year (Biomaterials, Jan'XXIV). The functionalized matrices supported adipose-derived stem cell differentiation into osteoblast lineages more effectively than commercial substrates through mechanisms involving integrin-mediated signaling pathways elucidated via RNA sequencing analysis.

Sustainable synthesis approaches employing renewable feedstocks were pioneered by MIT chemists who achieved scalable production using lignin-derived precursors through catalytic hydrogenation steps followed by chiral crystallization processes (Sustainable Chem Process, March'XXIV). This method reduces carbon footprint by ~70% compared to petrochemical-based syntheses while maintaining product purity standards required for biomedical use cases requiring USP/NF compliance documentation.

• 65355-32-0(trans-4'-Propyl-(1,1'-bicyclohexyl)-4-carboxylic Acid)
• 4331-54-8(4-methylcyclohexane-1-carboxylic acid)
• 7077-05-6(trans-4-Isopropylcyclohexanecarboxylic acid)
• 16052-40-7((1R,2S,5R)-2-Isopropyl-5-methylcyclohexanecarboxylic acid)
• 62067-45-2(4-isopropylcyclohexane carboxylic acid)
• 84976-67-0(trans-4'-Ethyl-(1,1'-bicyclohexyl)-4-carboxylic acid)
• 89111-63-7(trans-4-(trans-4-Butylcyclohexyl)Cyclohexanecarboxylic Acid)
• 6833-47-2(trans-4-Ethylcyclohexanecarboxylic acid)
• 3971-31-1(Cyclohexane-1,3-dicarboxylic Acid)
• 16526-68-4(rac-(1R,3S,5s)-cyclohexane-1,3,5-tricarboxylic acid, cis)