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Modification of oligo-Ricinoleic Acid and its derivatives with 10-undecenoic acid via lipase-catalyzed esterification

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dc.contributor.authorHayes, Douglas G.
dc.contributor.authorMannam, Vinay K.
dc.contributor.authorYe, Ran
dc.contributor.authorZhao, Haizhen
dc.contributor.authorOrtega Requena, Salvadora
dc.contributor.authorMontiel Morte, María Claudia
dc.contributor.departmentIngeniería Química
dc.contributor.otherFacultad de Química
dc.date.accessioned2026-02-25T08:47:45Z
dc.date.available2026-02-25T08:47:45Z
dc.date.copyright© 2012 by the authors
dc.date.issued2012-04-17
dc.description.abstractLipases 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.
dc.formatapplication/pdf
dc.format.extent19
dc.identifier.citationPolymers 2012, 4(2), 1037-1055
dc.identifier.doihttps://doi.org/10.3390/polym4021037
dc.identifier.eissn2073-4360
dc.identifier.urihttp://hdl.handle.net/10201/212762
dc.languageeng
dc.publisherMDPI
dc.relationFinancial support was kindly supplied by the (US) National Institutes of Health grant 5R03EB005664-02. S. Ortega was beneficiary of a pre-doctoral scholarship from Fundación Séneca of Murcia.M.C. Montiel was beneficiary of a José Castillejo fellowship from Ministerio de Ciencia e Innovación of Spain. Financial support allowing for the visit of Haizhen Zhao to the Hayes laboratory through the “International Exchange Program for Agri-food Quality and Safety” (948 Program from Ministry of Agriculture, project No. 2011-S10) is gratefully acknowledged.
dc.relation.publisherversionhttps://www.mdpi.com/2073-4360/4/2/1037
dc.rightsAttribution 4.0 International*
dc.rights.accessRightsinfo:eu-repo/semantics/openAccess
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/*
dc.subjectCastor oil
dc.subjectLipases
dc.subjectOligo-ricinoleic acid
dc.subjectPolyglycerol polyricinoleate
dc.subjectRicinoleic acid
dc.subject10-undecenoic acid
dc.subjectBiobased polyesters
dc.subject.odsNo relacionado con ningún objetivo de desarrollo sostenible
dc.titleModification of oligo-Ricinoleic Acid and its derivatives with 10-undecenoic acid via lipase-catalyzed esterification
dc.typeinfo:eu-repo/semantics/article
dc.type.versioninfo:eu-repo/semantics/publishedVersion
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relation.isAuthorOfPublication8ee9c913-ef71-490d-9528-1902126d91ca
relation.isAuthorOfPublicationc27d6b47-5627-4e89-b610-62b855de64c2
relation.isAuthorOfPublication.latestForDiscovery8ee9c913-ef71-490d-9528-1902126d91ca
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