Nonadecanedioic acid mono-t-butyl ester is a long-chain fatty diacid derivative with one protected terminus. The tert-butyl group offers selective reactivity for synthetic modifications and hydrolysis studies. Researchers use it to model lipid interaction, oxidative pathways, and ester-cleavage mechanisms. Its hydrophobic chain enhances membrane-partitioning investigations.
CAT No: 10-101-232
CAS No:1643852-37-2
Synonyms/Alias:19-(tert-Butoxy)-19-oxononadecanoic acid;1643852-37-2;Nonadecanedioic acid, 1-(1,1-dimethylethyl) ester;Nonadecanedioic acid mono-t-butyl ester;19-[(2-methylpropan-2-yl)oxy]-19-oxononadecanoic acid;SCHEMBL2037115;C23H44O4;MFCD30737821;AKOS037648764;BS-15520;CS-0137478;D80197;Nonadecanedioic acid mono (1,1-dimethylethyl) ester;
Nonadecanedioic acid mono-t-butyl ester is a specialized organic compound classified as a fatty acid ester, featuring a long-chain aliphatic backbone with a mono-tert-butyl ester functional group. Its unique structure imparts both hydrophobic and functionalized reactivity, making it valuable for a range of biochemical and synthetic chemistry applications. The presence of a single protected carboxyl group allows for selective chemical transformations, while the extended hydrocarbon chain facilitates its integration into lipid-like systems. Researchers and product developers leverage this compound for its role as an intermediate in complex molecule synthesis and its utility in materials science, lipid research, and surface chemistry studies.
Synthetic intermediate: One of the primary applications of nonadecanedioic acid mono-t-butyl ester is as a versatile intermediate in organic synthesis. The mono-protection of one carboxyl group enables selective functionalization at the other terminus, supporting the stepwise construction of complex molecules. Chemists often employ this ester in the synthesis of specialty polymers, dendrimers, or advanced surfactant molecules, where controlled reactivity and precise chain length are critical. Its use streamlines multi-step synthetic routes by offering orthogonal protection strategies and minimizing side reactions.
Lipid and membrane research: The compound's long aliphatic chain and amphiphilic character make it a useful tool in studies of lipid bilayers, membrane models, and surface-active agents. By incorporating the mono-t-butyl ester into artificial membranes or vesicle systems, researchers can investigate the effects of chain length, hydrophobicity, and terminal functionality on membrane stability, permeability, and protein-lipid interactions. Such studies contribute to a deeper understanding of biomimetic membrane design and the development of novel lipid-based delivery systems.
Surface modification: Nonadecanedioic acid mono-t-butyl ester is frequently utilized in surface engineering for the functionalization of nanoparticles, polymers, or inorganic substrates. The protected carboxyl group allows for controlled deprotection and subsequent covalent attachment to surfaces, enabling the creation of tailored monolayers or surface coatings. These modified surfaces can be exploited for applications in biosensing, antifouling materials, or the fabrication of hydrophobic and oleophobic interfaces, where precise molecular architecture is essential for performance.
Analytical reference material: The defined structure and functional group arrangement of this ester make it a valuable reference standard in analytical chemistry. It can be employed in chromatographic method development, mass spectrometry calibration, or as a marker compound in the analysis of synthetic transformations. Its predictable behavior under analytical conditions helps validate instrument performance and ensures reproducibility in quantitative studies.
Materials science research: Due to its structural features, nonadecanedioic acid mono-t-butyl ester serves as a building block in the design of advanced materials. Researchers incorporate it into the synthesis of specialty polymers, cross-linkers, or self-assembling systems where long-chain diacid derivatives with defined protection patterns are required. The compound's adaptability facilitates the exploration of new material properties, such as enhanced thermal stability, controlled degradation rates, or unique surface characteristics, broadening the scope of functional material development in both academic and industrial settings.
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