53481-04-2

Usage

Classification

Naturally occurring fatty acid

Occurrence

Found in various plants and animals

Structure

Carboxylic acid with a long carbon chain of 20 atoms

Double bond

Located at the 10th carbon

Properties

Anti-inflammatory

Therapeutic potential

Studied for treating chronic inflammatory diseases

Additional activity

Exhibits antioxidant properties

Rarity

Relatively rare fatty acid

Interest

Potential pharmaceutical and medicinal applications

Upstream product

• 112-38-9 10-undecenoic acid 

Downstream Products

• 111-20-6 1,10-decanedioic acid 
• 2424-92-2 octadecane-1,18-dicarboxylic acid 

Relevant academic research and scientific papers

Method of producing dicarboxylic acids

A method of producing dicarboxylic acids (e.g., α,ω dicarboxylic acids) by reacting a compound having a terminal COOH (e.g., unsaturated fatty acid such as oleic acid) and containing at least one carbon-carbon double bond with a second generation Grubbs catalyst in the absence of solvent to produce dicarboxylic acids. The method is conducted in an inert atmosphere (e.g., argon, nitrogen). The process also works well with mixed unsaturated fatty acids obtained from soybean, rapeseed, tall, and linseed oils.

Metathesis of unsaturated fatty acids: Synthesis of long-chain unsaturated-α,ω-dicarboxylic acids

The self-metathesis of readily available monounsaturated FA has the potential of being an important pathway for the synthesis of symmetrical long-chain unsaturated-α,ω-dicarboxylic acids (C18-C 26). Previous studies on the self-metathesis of monounsaturated FA esters using ruthenium catalysts in solution, however, suffered from low conversions as a result of the thermodynamic control of the reaction. We have found that the secondgeneration Grubbs catalyst can effectively catalyze the solventfree self-metathesis of monounsaturated FA of varying purity (from 90 to 99%) to afford two important products-monounsaturated dicarboxylic acids and hydrocarbons-in very high molar conversions (>80%). This solvent-free self-metathesis reaction also works for monounsaturated FA containing additional functional groups. Reactions were conducted at catalyst loadings as low as 0.005 mol%, and turnover numbers as high as 10,800 could be obtained. This discovery represents an attractive approach to the large-scale production of useful monounsaturated-α,ω-dicarboxylic acids and long-chain unsaturated hydrocarbons by means of this solvent-free ruthenium-catalyzed self-metathesis of readily available monounsaturated FA. Copyright