Modification of oligo-Ricinoleic Acid and Its Derivatives with 10-Undecenoic Acid via Lipase-Catalyzed Esterification

Abstract

Lipases were employed under solvent-free conditions to conjugate oligo-ricinoleic acid derivatives with 10-undecenoic acid, to incorporate a reactive terminal double bond into the resultant product. First, undecenoic acid was covalently attached to oligo-ricinoleic acid using immobilized Candida antarctica lipase (CAL) at a 30% yield. Thirty percent conversion also occurred for CAL-catalyzed esterification between undecenoic acid and biocatalytically-prepared polyglycerol polyricinoleate (PGPR), with attachment of undecenoic acid occurring primarily at free hydroxyls of the polyglycerol moiety. The synthesis of oligo-ricinoleyl-, undecenoyl-structured triacylglycerols comprised two steps. The first step, the 1,3-selective lipase-catalyzed interesterification of castor oil with undecenoic acid, occurred successfully. The second step, the CAL-catalyzed reaction between ricinoleyl-, undecenoyl structured TAG and ricinoleic acid, yielded approximately 10% of the desired structured triacylglycerols (TAG); however, a significant portion of the ricinoleic acid underwent self-polymerization as a side-reaction. The employment of gel permeation chromatography, normal phase HPLC, NMR, and acid value measurements was effective for characterizing the reaction pathways and products that formed. OPEN ACCESSPolymers 2012, 4 1038

Effects of Particle Size of Sucrose Suspensions and Pre‐incubation of Enzymes on Lipase‐Catalyzed Synthesis of Sucrose Oleic Acid Esters

“…The conventional chemical synthesis of sugar fatty acid esters is associated with extreme reaction conditions, for instance, high temperature and the employment of amounts of alkali or acid catalysts [11]. In contrast, biocatalytic synthesis occurs in mild reaction conditions, thereby reducing the formation of undesirable by-products and lowering energy consumption during processing [12]. In the literature, numerous approaches for lipase-catalyzed reactions have been conducted, including polar solvents [13][14][15], ionic liquids [16][17][18], microwave assistance [19], ultrasound irradiation [20], and supercritical carbon dioxide [21], to overcome the poor miscibility of acyl donors and acceptors reviewed in the publications [22,23].Recently, saccharide fatty acid esters have been enzymatically synthesized in solvent-free media in our laboratory, by making use of the desired product, monoester, to enhance the miscibility of acyl acceptor and donor, saccharide and fatty acid, respectively [24][25][26][27].…”

Selectivity of lipases for estolides synthesis

“…Even though such substrates have been already tested, especially ricinoleic acid, alone [10] or in combination with different polyols or fatty acids [21], there are no reports concerning the selectivity of several commercially available lipases, as we performed in this study. Moreover, in previous reports substrate conversion or chain elongation have been monitored solely by titration [9] or thin layer chromatography [14].…”

Enhanced Ricinoleic Acid Preparation Using Lipozyme TLIM as a Novel Biocatalyst: Optimized by Response Surface Methodology

“…Ricinoleic acid (RA), also known as cis-12-hydroxy-9-octadecenoic acid, is the only industrial fatty acid containing a hydroxy group in nature [1] and can be used as raw material for skin care products, plasticizers, emulsifiers, lubricants, and nanomaterials [2][3][4][5][6][7][8]. Castor oil (CO) is one kind of nonedible oil derived from the plant seeds of Ricinus communis [1,9].…”