11-Hydroxyundecanoic Acid (CAS 3669-80-5): A Versatile Chemical Intermediate for Diverse Industries

In the vast landscape of organic chemistry, certain compounds stand out due to their exceptional versatility and wide-ranging applications. Among these, 11-Hydroxyundecanoic Acid (CAS NO: 3669-80-5) shines as a pivotal chemical intermediate. This long-chain fatty acid derivative is gaining increasing attention across various sectors, including pharmaceuticals, specialty chemicals, and advanced material science, owing to its unique molecular structure and reactivity.

Known by synonyms such as 11-hydroxy-undecanoic acid and Undecanoic acid, 11-hydroxy, this compound possesses the molecular formula C11H22O3 and a molecular weight of approximately 202.29. Its distinct properties include a melting point typically ranging from 64-69 °C and a boiling point around 345 °C at 760mmHg, making it a stable solid for handling and storage. Visually, it appears as a white powder or solid. These characteristics underscore its utility as a foundational building block in complex synthesis pathways.

The applications of 11-Hydroxyundecanoic Acid are remarkably diverse. It serves as a crucial intermediate in the synthesis of various pharmaceutical compounds, contributing to the development of new drug candidates. In the realm of specialty chemicals, its unique chemical handle, comprising both a hydroxyl group and a carboxylic acid group, allows for sophisticated derivatization reactions. This makes it indispensable for creating advanced polymers, lubricants, and surfactants. Furthermore, research indicates its potential in biochemical studies, where it has been observed to impede acyl-CoA synthetase activity—an enzyme vital for fatty acid metabolism—and activate peroxisome proliferator-activated receptor alpha (PPARα), a key regulator of lipid metabolism. Its role extends to the production of nylon monomers, highlighting its significance in green chemistry initiatives and the utilization of renewable resources.

The synthesis of 11-Hydroxyundecanoic Acid employs various methods, reflecting its growing demand. Modern approaches often leverage sustainable feedstocks, such as ricinoleic acid (12-hydroxyoleic acid), through innovative chemo-enzymatic routes. This not only showcases efficiency in production but also aligns with the global shift towards environmentally conscious manufacturing practices. Other common starting materials include 10-undecenoic acid and 11-bromoundecanoic acid, allowing for flexible and adaptable production strategies.

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