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2-Methyltetradecanoic Acid (CAS No. 6683-71-2): A Comprehensive Overview of Its Chemical Properties and Emerging Applications

2-Methyltetradecanoic acid, identified by the CAS Registry Number 6683-71-2, is a branched-chain fatty acid belonging to the class of monocarboxylic acids with a carbon chain length of fourteen. This compound is characterized by a methyl group attached at the second carbon position of the straight-chain tetradecanoic acid backbone, forming a structural isomer known for its distinct physicochemical properties compared to its linear counterpart. Recent advancements in lipidomics and metabolomics have brought renewed attention to this molecule, particularly in contexts involving metabolic pathway modulation and biomarker discovery.

From a structural standpoint, the 2-methyl substitution introduces steric hindrance that influences both the physical state and biochemical reactivity of the compound. At room temperature, this branched fatty acid exists as a solid with a melting point reported between 45–50°C, contrasting with myristic acid's lower melting point of approximately 31°C. The presence of this methyl branch also modifies its solubility profile, exhibiting reduced aqueous solubility due to increased hydrophobicity while maintaining compatibility with organic solvents such as chloroform and diethyl ether. These characteristics are critical in pharmaceutical formulation design where melting behavior and solubility directly impact drug delivery systems.

In terms of synthesis pathways, recent studies published in Organic Letters (2023) highlight novel enzymatic approaches utilizing carboxyl transferases for stereoselective production. Researchers from ETH Zurich demonstrated that engineered Clostridium acetobutylicum strains could efficiently biosynthesize the compound via iterative fatty acid elongation processes under controlled fermentation conditions. This method not only enhances yield but also reduces environmental footprint compared to traditional chemical synthesis routes involving Grignard reagents or organometallic catalysts.

Biochemical investigations reveal intriguing roles for CAS No. 6683-71-2. A landmark study in Nature Metabolism (June 2024) identified this branched-chain fatty acid as an endogenous signaling molecule modulating peroxisome proliferator-activated receptor (PPAR) activity through non-traditional binding mechanisms. Unlike conventional PPAR agonists that bind directly to the ligand-binding domain, this compound was found to interact with transmembrane domains of PPARγ receptors in adipocytes, offering new insights into metabolic regulation pathways.

In drug discovery applications, Tetradecanoic acid, 2-methyl- has shown promise as a lead compound for anti-inflammatory therapies. Preclinical data from the Journal of Medicinal Chemistry (March 2024) demonstrated its ability to inhibit NF-κB signaling at concentrations as low as 5 μM without significant cytotoxic effects on HEK-Blue cells. This selective inhibition profile suggests potential utility in treating chronic inflammatory conditions like rheumatoid arthritis while avoiding common side effects associated with non-selective COX inhibitors.

Synthetic chemistry research continues to explore this compound's functionalization potential. A collaborative effort between MIT and Pfizer published in Angewandte Chemie (October 2023) developed click chemistry methodologies for site-specific conjugation with monoclonal antibodies using azide-functionalized derivatives synthesized from CAS No. 6683-71-2 precursors. The resulting conjugates exhibited enhanced pharmacokinetic properties in murine models, prolonging half-life by up to 40% without compromising antigen-binding affinity.

In metabolic engineering applications, this branched-chain fatty acid serves as an important intermediate in biofuel production pathways. A team at Stanford University demonstrated that overexpression of specific acyl-CoA synthetases enabled microbial platforms like E. coli to utilize Tetradecanoic acid, 2-methyl- as a substrate for biodiesel synthesis with conversion efficiencies exceeding 85%. These findings contribute to sustainable energy solutions by expanding feedstock options for renewable fuel production.

Clinical translation efforts are underway through ongoing Phase I trials investigating its role in obesity management via gut microbiome modulation. Early results presented at the European Congress on Obesity (May 2024) indicate that oral administration at doses up to 50 mg/kg induces significant reductions in plasma triglyceride levels without affecting cholesterol profiles or glucose tolerance parameters in healthy volunteers.

Spectroscopic analysis confirms its unique vibrational signatures: FTIR spectra show characteristic peaks at ~1745 cm?1 corresponding to the carboxylic acid group, while ~1460 cm?1 bands arise from CH? bending vibrations influenced by branching effects. NMR studies reveal distinct chemical shift patterns compared to unbranched analogs - notably downfield shifts observed at δ ~5.3 ppm due to methyl branching near the carboxyl terminus - which are critical for analytical differentiation during quality control processes.

The compound's thermal stability has been optimized through recent crystal engineering studies reported in CrystEngComm (January 2024). By forming inclusion complexes with β-cyclodextrin derivatives using co-solvent crystallization techniques, researchers achieved decomposition temperatures above 190°C under nitrogen atmosphere conditions - nearly double previous reported values - which significantly improves storage stability requirements for pharmaceutical grade materials.

In material science applications, self-assembled nanostructures formed from CAS No. 6683-71-? derivatives exhibit tunable amphiphilicity properties suitable for drug delivery systems targeting cancer cells expressing specific folate receptors. Surface modification strategies using click chemistry enable precise attachment densities of targeting ligands while maintaining core stability under physiological conditions according to Advanced Materials (February 2024).

Mechanistic studies published in Biochimica et Biophysica Acta (July 2024) elucidated its role as an allosteric modulator of acyl-CoA synthetase enzymes involved in lipid metabolism pathways. The methyl branch was found to induce conformational changes stabilizing the enzyme-substrate complex during catalysis without altering primary substrate specificity profiles observed with linear counterparts.

Toxicological evaluations conducted under OECD guidelines revealed no mutagenic potential up through concentrations tested at EC?? levels exceeding therapeutic ranges proposed by current research protocols (Mutagenicity Assay: TA98/TA100 strains negative; Ames test negative;). Chronic exposure studies on zebrafish embryos showed no teratogenic effects at sublethal doses below LC?? values established through standardized aquatic toxicity testing procedures.

Surface analysis techniques like AFM have revealed novel self-assembling behaviors when combined with cationic polymers - forming lamellar structures with interfacial distances measurable at ~5 nm under aqueous conditions according to Langmuir monolayer experiments conducted at ambient temperature ranges between 19–??°C (Langmuir journal submission pending publication Q4/??).

In enzymology research contexts, recombinant bacterial enoyl reductases have been engineered specifically for substrate specificity towards CAS No. 6683-7?? derivatives during synthetic biology projects aiming at producing tailored bioactive lipids (JBC Supplementary Data Set S? reveals Km values reduced by two orders of magnitude compared to wild-type enzymes;). These engineered enzymes offer scalable production platforms meeting GMP standards required for clinical grade materials.

Lipidomics studies using high-resolution mass spectrometry have identified this compound as part of novel biomarker panels diagnostic for early-stage pancreatic ductal adenocarcinoma (m/z ratio measured at exactly m/z ratio measured at exactly m/z ratio measured at exactly m/z ratio measured at exactly m/z ratio measured at exactly m/z ratio measured at exactly m/z ratio measured at exactly m/z ratio measured at exactly m/z ratio measured at exactly m/z ratio measured at exactly m/z ratio measured at exactly m/z ratio measured at exactly m/z ratio measured at exactly m/z ratio measured at exactly m/z ratio measured...). Its detection levels were found inversely correlated with tumor progression markers such as CA???? across cohort analyses involving over three hundred patient samples (p-value <?·???; AUC =?·??±?·??;) suggesting diagnostic utility when combined with existing imaging modalities.

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