| Synonym: | 18-(tert-Butoxy)-18-oxooctadecanoic acid |
| CAS #: | 843666-40-0 |
| Molecular Formula: | C22H42O4 |
| Molecular Weight: | 370.6 |
| Octadecanedioic acid mono-tert-butyl ester, is a highly versatile chemical compound that has garnered significant attention in various fields, particularly in pharmaceuticals, polymer chemistry, and materials science. This monoester of octadecanedioic acid is characterized by its long hydrocarbon chain and a tert-butyl ester group, which collectively impart unique chemical and physical properties crucial for its diverse applications. 1. Applications Octadecanedioic acid mono-tert-butyl ester is a highly valued intermediate and component across several industries: 1.1 Pharmaceutical Industry (Drug Synthesis): • GLP-1 Analogs: A prominent application is its use as a chemical intermediate for the synthesis of long-acting, potent Exendin-4 based GLP-1 analogs. These analogs are crucial for the treatment of diabetes and related metabolic disorders, as they provide sustained glycemic control. Semaglutide, a well-known GLP-1 analog, utilizes this compound in its side chain synthesis. • Drug Delivery Systems: Its unique structure allows for its utilization in the development of microstructure-based transdermal drug delivery systems, where it can enhance the solubility and bioavailability of certain medications, offering controlled release. • Linker Chemistry: It serves as a non-cleavable linker in the synthesis of complex pharmaceutical molecules like Antibody-Drug Conjugates (ADCs) and Proteolysis Targeting Chimeras (PROTACs). Its carboxylic acid can be reacted with alcohols or amines, while the tert-butyl ester can be deprotected for further conjugation, making it a flexible building block. • Somatostatin Preparation: It is also noted as a pharmaceutical intermediate in the preparation of somatostatin analogs. 1.2 Polymer Chemistry and Materials Science • Plasticizer: Its long hydrocarbon chain contributes to its role as an effective plasticizer in the production of flexible polymers. It improves their durability and flexibility, making it essential in industries like packaging, automotive, and electronics. • Biodegradable Polymers: It is a valuable component in the synthesis of biodegradable polymers, aligning with the increasing demand for sustainable and eco-friendly materials. Its integration contributes to the production of biodegradable plastics, addressing environmental concerns. • Specialty Resins and Coatings: It serves as a key intermediate in the production of polyesters, polyamides, and specialty resins used in high-performance automotive and electronic coatings. Its thermal stability and solubility are advantageous for these applications. • Lubricant Additives: It can enhance viscosity and wear resistance in synthetic oils, contributing to advanced lubricant formulations. • Adhesives & Sealants: It improves flexibility and adhesion in high-strength bonding agents. • R&D Building Block: Used as a versatile building block for novel biodegradable materials and nanostructured polymers in research and development. 2. Key Characteristics and Advantages • Bifunctionality: The presence of both a free carboxylic acid and a tert-butyl ester allows for selective reactions and differential deprotection, making it a powerful intermediate in multi-step syntheses. • Protecting Group: The tert-butyl ester serves as a robust protecting group for one of the carboxylic acids, which can be selectively removed under mild acidic conditions (e.g., with trifluoroacetic acid) without affecting other sensitive functionalities. • Long Hydrocarbon Chain: The 18-carbon chain imparts lipophilicity and specific rheological properties, which are beneficial in drug delivery (e.g., albumin binding for extended half-life in GLP-1 analogs), polymer applications, and cosmetic formulations. • Solubility: Known for its excellent solubility in organic solvents, facilitating its use in various formulations and synthesis processes. • Stability: Possesses good thermal stability, making it suitable for high-heat polymer processing and industrial formulations. Low volatility contributes to long-lasting performance in formulations. Octadecanedioic acid mono-tert-butyl ester (CAS 843666-40-0) is a crucial and versatile chemical building block. Its unique structure, featuring a long aliphatic chain and differentially protected carboxylic acid functionalities, makes it an indispensable intermediate in the synthesis of advanced pharmaceuticals (especially for long-acting peptide drugs), high-performance polymers, and specialized materials. |
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Octadecanedioic acid mono-tert-butyl ester
For Research & Development use only. Not for testing and/or use on humans.
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