10-Undecenoic acid, methyl ester
10-Undecenoic acid, methyl ester, also known as methyl undecylenate (CAS 111-81-9), is a clear, colorless to pale yellow liquid fatty acid ester derived primarily from the pyrolysis of castor oil derivatives. It is characterized by its linear twelve-carbon chain featuring a terminal double bond, which provides a reactive site for various chemical transformations. This compound is valued for its distinctive fatty, fruity, and slightly wine-like aromatic profile, making it a versatile component in both industrial and specialty chemical sectors.
In a research and manufacturing context, this ester serves as a critical building block due to its dual functionality—the ester group and the terminal alkene. It exhibits good stability under standard storage conditions but should be handled with care to avoid oxidation of the unsaturated bond. Its derivation from renewable castor oil sources aligns it with green chemistry initiatives, providing a sustainable alternative for synthesizing complex organic molecules and high-performance materials.
• Chemical Synthesis and Intermediates: Methyl 10-undecenoate acts as a primary precursor for the synthesis of various specialty chemicals, including 11-aminoundecanoic acid, which is a key monomer for producing high-performance Nylon-11. The terminal double bond allows for functionalization through hydroformylation, metathesis, or thiol-ene addition, enabling the creation of diverse polymers, surfactants, and lubricants.
• Fragrance and Flavor Industry: Due to its unique organoleptic properties, this ester is frequently employed as a flavoring agent and fragrance ingredient. It contributes fatty, waxy, and rose-like notes to perfumes and cosmetic formulations. Its ability to blend well with other aliphatic esters makes it useful in creating complex floral or fruity bouquets in soaps, detergents, and personal care products.
• Agricultural and Pheromone Research: The compound serves as a vital intermediate in the production of insect pheromones and agricultural semiochemicals. Its specific chain length and terminal unsaturation mimic natural biological precursors, allowing researchers to synthesize pheromone components used in integrated pest management systems to develop environmentally friendly solutions for crop protection.
• Coatings and Surface Modifiers: In the materials science sector, 10-undecenoic acid methyl ester is utilized to modify resins and develop specialized coatings. It can be incorporated into alkyd resins to improve flexibility and water resistance. Additionally, it is explored in the synthesis of bio-based plasticizers and additives that enhance the mechanical properties of biodegradable plastics.
Product Name: 10-Undecenoic acid, methyl ester
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