Octadecanedioic acid is an alpha,omega-dicarboxylic acid that is octadecane in which both terminal methyl groups have been replaced by carboxy groups. It is an alpha,omega-dicarboxylic acid and an octadecane. It is a conjugate acid of an octadecanedioate and an octadecanedioic acid anion.
CAT No: HB00132
CAS No:871-70-5
Synonyms/Alias:Octadecanedioic acid;871-70-5;1,18-Octadecanedioic acid;1,16-Hexadecanedicarboxylic acid;Octadecane-1,18-dioic acid;1,18-Octadecadioic acid;RSZ6PQ0QQJ;UNII-RSZ6PQ0QQJ;Hexadecanedicarboxylic acid;MFCD00142369;DTXSID1074331;CHEBI:133086;Octadecanedioate;1,18-Octadecanedioate;1,16-Hexadecanedicarboxylate;ODDA;1,18-Octadecadioate;18-octadecanedioic acid;SCHEMBL35775;DTXCID9048564;1,16-hexadecane dicarboxylic acid;BCP32531;LMFA01170029;AKOS015839857;CS-W005178;FO75325;GS-3421;HY-W005178;AC-32514;SY025879;NS00006357;O0222;A842023;1,18-Octadecadioic acid;Octadecane-1,18-dioic acid;Q27288272;442-490-2;617-978-5;
Octadecanedioic Acid is a long-chain aliphatic dicarboxylic acid, structurally characterized by an 18-carbon backbone terminated by carboxylic acid groups at both ends. As a saturated diacid, it occupies a unique niche in biochemical and industrial research due to its amphiphilic properties, chemical stability, and compatibility with both organic and aqueous systems. Its molecular architecture makes it particularly valuable for studies involving lipid metabolism, polymer synthesis, and the investigation of fatty acid derivatives. The compound's relevance extends across multiple scientific disciplines, including biochemistry, materials science, and analytical chemistry, where its dual functionality and chain length offer distinctive advantages for probing structure-function relationships and developing advanced materials.
Metabolic research: Octadecanedioic acid is widely employed as a model substrate in studies of fatty acid metabolism and peroxisomal β-oxidation. Its resistance to complete catabolism by mitochondrial pathways, compared to monocarboxylic fatty acids, enables researchers to dissect the specific roles of peroxisomes in long-chain dicarboxylic acid degradation. The compound is thus instrumental in elucidating the biochemical mechanisms underlying lipid metabolic disorders and in exploring the enzymatic specificity of acyl-CoA oxidases and related enzymes.
Polymer and materials science: The dicarboxylic acid functionality of octadecanedioic acid makes it a valuable monomer for the synthesis of polyamides, polyesters, and other specialty polymers. In materials research, it is utilized to generate high-performance polymers with enhanced hydrophobicity, flexibility, and thermal stability. Its long aliphatic chain imparts unique mechanical and physicochemical properties to the resulting materials, supporting the development of advanced coatings, fibers, and engineering plastics with tailored performance characteristics.
Surface modification: In surface chemistry, octadecanedioic acid serves as an effective agent for the functionalization of metal, metal oxide, and nanoparticle surfaces. Its amphiphilic structure facilitates the formation of self-assembled monolayers and covalent attachment to substrates, thereby modifying surface energy, wettability, and chemical reactivity. Such surface modifications are crucial for applications in sensor development, catalysis, and the fabrication of biocompatible interfaces.
Analytical standards and method development: The compound is frequently used as an internal or calibration standard in analytical techniques such as gas chromatography and mass spectrometry. Its well-defined structure and stability under analytical conditions make it suitable for quantifying long-chain dicarboxylic acids in complex biological or environmental samples. This application supports the accurate measurement of metabolic intermediates, environmental contaminants, and the assessment of lipid oxidation products.
Synthesis of specialty chemicals: Octadecanedioic acid is also utilized as a precursor for the preparation of specialty intermediates, surfactants, and lubricants. Its bifunctional nature allows for diverse chemical transformations, including esterification, amidation, and salt formation, which are exploited in the design of novel molecules with tailored amphiphilic or surface-active properties. These downstream products find use in research contexts where controlled hydrophobicity and chain length are critical to experimental outcomes or product performance.
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