Heneicosanedioic acid

Heneicosanedioic acid is a long-chain fatty acid.

Designed for biological research and industrial applications, not intended for individual clinical or medical purposes.
Heneicosanedioic acid(CAS 505-55-5)

CAT No: 10-101-227

CAS No:505-55-5

Synonyms/Alias:Heneicosanedioic acid;Henicosanedioic acid;505-55-5;Henicosanedioicacid;Japonic acid;japanic acid;Japonic-acid;Heni-cosanedioic acid;Heneicosa-1,21-dioic acid;73CA8QKN34;japansaure;MFCD00045934;UNII-73CA8QKN34;SCHEMBL1674812;CHEBI:165385;LMFA01170036;BS-44443;SY248589;E74401;

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M.F/Formula
C21H40O4
M.W/Mr.
356.5

Heneicosanedioic acid, also known as 1,21-Docosanedioic acid, is a long-chain dicarboxylic acid characterized by its 21-carbon backbone and two terminal carboxyl groups. This unique molecular structure imparts exceptional versatility, making it a valuable intermediate in both academic and industrial research. The compound's amphiphilic nature, resulting from its hydrophobic alkyl chain and hydrophilic carboxyl functionalities, enables it to participate in a wide array of chemical transformations. Its stability, compatibility with various organic solvents, and potential for derivatization further enhance its appeal as a building block for advanced material synthesis, specialty polymers, and surface modification agents. Researchers recognize heneicosanedioic acid for its ability to facilitate the construction of complex molecular architectures, thanks to its dual reactive sites and robust carbon skeleton.

Polymer Synthesis: Heneicosanedioic acid serves as a critical monomer in the production of specialty polyamides and polyesters. Its long aliphatic chain introduces flexibility and hydrophobicity to polymer backbones, resulting in materials with enhanced mechanical properties and chemical resistance. By reacting with diamines or diols, the dicarboxylic acid enables the formation of high-molecular-weight polymers, which find use in engineering plastics, high-performance fibers, and coatings. The unique chain length of this compound allows for fine-tuning of polymer crystallinity and melting behavior, offering material scientists a powerful tool for customizing polymer performance for specific applications.

Surface Modification and Functionalization: In surface science, 1,21-Docosanedioic acid is employed to modify and functionalize a variety of substrates, including metals, nanoparticles, and polymers. Through the formation of self-assembled monolayers (SAMs), it imparts hydrophobic barriers or tailored interfacial properties to surfaces, enhancing their resistance to corrosion, fouling, or unwanted adsorption. The terminal carboxyl groups provide anchor points for further chemical modification, enabling the attachment of bioactive molecules, dyes, or catalysts. This versatility supports the development of advanced sensors, biomedical devices, and smart coatings with tunable surface characteristics.

Organic Synthesis Intermediate: As a versatile intermediate, heneicosanedioic acid is utilized in organic synthesis for the preparation of complex molecules and functional derivatives. Its two carboxyl groups can be selectively activated or transformed into esters, amides, or anhydrides, serving as key intermediates in multi-step synthetic routes. Chemists leverage its long carbon chain to introduce spacing or flexibility between functional groups in target molecules, which is particularly valuable in the design of molecular spacers, dendrimers, or macrocycles. The compound's reactivity and compatibility with various coupling reagents expand its utility in constructing architecturally diverse compounds for research and development.

Material Science Research: In material science, 1,21-Docosanedioic acid is investigated for its role in the design of supramolecular assemblies, nanostructures, and hybrid materials. Its amphiphilic structure promotes self-organization in solution or at interfaces, enabling the formation of micelles, vesicles, or layered assemblies. These properties are exploited in the fabrication of nanomaterials for electronic, optical, or catalytic applications. The acid's ability to interact with both hydrophobic and hydrophilic domains allows researchers to tailor material properties for specific functions, such as controlled release, selective adsorption, or enhanced conductivity.

Analytical Chemistry and Standardization: Analytical laboratories utilize heneicosanedioic acid as a reference compound or calibration standard in chromatographic and spectroscopic analyses. Its well-defined structure and physicochemical properties make it suitable for method development, instrument calibration, and quality control in the analysis of long-chain fatty acids and related compounds. By providing a reliable benchmark, it supports the accurate quantification and identification of analytes in complex mixtures, thereby contributing to the advancement of analytical techniques in environmental, food, and industrial chemistry.

Biochemical Studies and Lipid Research: In the context of biochemical research, 1,21-Docosanedioic acid is explored as a model compound for studying the metabolism and enzymatic transformation of long-chain dicarboxylic acids. Researchers employ it to investigate the oxidative pathways, transport mechanisms, and functional roles of similar molecules in biological systems. Its structural features facilitate the elucidation of enzyme specificity, substrate recognition, and metabolic regulation, offering insights into lipid biochemistry and the development of analytical assays for related biomolecules.

Shipping Condition
Room temperature in continental US; may vary elsewhere.
InChI
InChI=1S/C21H40O4/c22-20(23)18-16-14-12-10-8-6-4-2-1-3-5-7-9-11-13-15-17-19-21(24)25/h1-19H2,(H,22,23)(H,24,25)
InChI Key
PWLXTFFHCFWCGG-UHFFFAOYSA-N

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