{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,11,4]],"date-time":"2025-11-04T10:37:11Z","timestamp":1762252631695,"version":"3.41.2"},"reference-count":25,"publisher":"Wiley","issue":"1","license":[{"start":{"date-parts":[[2017,10,16]],"date-time":"2017-10-16T00:00:00Z","timestamp":1508112000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100001871","name":"Funda\u00e7\u00e3o para a Ci\u00eancia e a Tecnologia","doi-asserted-by":"publisher","award":["UID\/AGR\/04129\/2013"],"award-info":[{"award-number":["UID\/AGR\/04129\/2013"]}],"id":[{"id":"10.13039\/501100001871","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Euro J Lipid Sci &amp; Tech"],"published-print":{"date-parts":[[2018,1]]},"abstract":"<jats:sec><jats:label\/><jats:p>Low calorie triacylglycerols (TAG) presenting medium\u2010chain fatty acids (M) at positions <jats:italic>sn<\/jats:italic>\u20101,3 and long\u2010chain fatty acids (L) at position <jats:italic>sn<\/jats:italic>\u20102 are known as MLM. This study aims at the production of MLM by acidolysis of grapeseed oil with medium\u2010chain caprylic (C8:0) or capric (C10:0) acids. Grapeseed oil is used as source of long\u2010chain polyunsaturated fatty acids (FAs), especially linoleic acid, at <jats:italic>sn<\/jats:italic>\u20102 position in TAG. Reactions are performed in batch, in solvent\u2010free systems, during 48\u2009h. Novel non\u2010commercial <jats:italic>sn<\/jats:italic>\u20101,3 regioselective lipases are used as alternative to high\u2010cost commercial biocatalysts, namely, the heterologous lipase from <jats:italic>Rhizopus oryzae<\/jats:italic> (rROL) immobilized in Amberlite\u2122 IRA 96 and <jats:italic>Carica papaya<\/jats:italic> lipase (CPL) self\u2010immobilized in papaya latex. The highest productions of new TAG are achieved at 40\u2009\u00b0C, molar ratio TAG:M of 1:2, after 48\u2009h, with both biocatalysts, with yields varying between 38 and 69%. rROL immobilized in Amberlite IRA 96 shows a preference toward caprylic acid while CPL shows no preference toward caprylic or capric acid. First\u2010order deactivation kinetics is observed for both biocatalysts. Half\u2010lives at 40\u2009\u00b0C are 166 and 118\u2009h for rROL and 96 and 81\u2009h for CPL, in the acidolysis of grapeseed oil with C8:0 or C10:0, respectively.<\/jats:p><jats:p><jats:bold>Practical Applications:<\/jats:bold> Grapeseeds of <jats:italic>Vitis vinifera<\/jats:italic> L. are a by\u2010product of the wine industry. Using grapeseed oil to produce added\u2010value functional oils rich in linoleic acid (essential fatty acid) may be a way of improving the revenues of the enological and oil sectors. Both lipases, and mainly Carica papaya lipase self\u2010immobilized in papaya latex, due to its low\u2010cost production and easy preparation, are promising non\u2010commercial biocatalysts for the synthesis of MLM in solvent\u2010free media. The use of a solvent\u2010free system, in addition of being a green option, is also preferred for economic reasons, avoiding the costs with solvent and solvent recovery. Also, the use of the stoichiometric molar ratio TAG:M of 1:2 will 1) decrease costs related with the recovery and reutilization of medium chain fatty acids in excess, product recovery and purification, and 2) avoid biocatalyst deactivation by high amounts of free fatty acids in reaction media.<\/jats:p><jats:p><jats:inline-graphic xmlns:xlink=\"http:\/\/www.w3.org\/1999\/xlink\" xlink:href=\"graphic\/ejlt201700320-gra-0001.png\" xlink:title=\"ejlt201700320-gra-0001\"\/><\/jats:p><jats:p>Both Carica papaya lipase (CPL) self\u2010immobilized in papaya latex and rROL in Amberlite IRA 96 catalyze the synthesis of MLM from grapeseed oil in solvent\u2010free medium. The highest productions of new TAG are achieved at 40\u2009\u00b0C, molar ratio TAG:M of 1:2, after 48\u2009h, with both biocatalysts, with yields varying between 38 and 69%. rROL immobilized in Amberlite IRA96 shows a preference toward caprylic acid while CPL shows no preference toward caprylic or capric acid.<\/jats:p><\/jats:sec>","DOI":"10.1002\/ejlt.201700320","type":"journal-article","created":{"date-parts":[[2017,9,22]],"date-time":"2017-09-22T10:26:58Z","timestamp":1506076018000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":29,"title":["Production of MLM Type Structured Lipids From Grapeseed Oil Catalyzed by Non\u2010Commercial Lipases"],"prefix":"10.1002","volume":"120","author":[{"given":"Carolina M.","family":"Costa","sequence":"first","affiliation":[{"name":"Universidade de Lisboa, Instituto Superior de Agronomia LEAF, Linking Landscape, Environment, Agriculture and Food Tapada da Ajuda 1349\u2010017 Lisbon Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1854-7042","authenticated-orcid":false,"given":"Nat\u00e1lia M.","family":"Os\u00f3rio","sequence":"additional","affiliation":[{"name":"Instituto Polit\u00e9cnico de Set\u00fabal Escola Superior de Tecnologia do Barreiro Rua Am\u00e9rico da Silva Marinho 2839\u2010001 Lavradio Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8980-6996","authenticated-orcid":false,"given":"Albert","family":"Canet","sequence":"additional","affiliation":[{"name":"Departament d'Enginyeria Quimica Biol\u00f2gica i Ambiental (EE) Universitat Aut\u00f2noma de Barcelona 08193 Bellaterra Barcelona Spain"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4650-4605","authenticated-orcid":false,"given":"Ivanna","family":"Rivera","sequence":"additional","affiliation":[{"name":"Centro de Investigaci\u00f3n y Asistencia en Tecnolog\u00eda y Dise\u00f1o del Estado de Jalisco (CIATEJ) Av Normalistas 800 44270 Guadalajara Jalisco Mexico"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9105-0702","authenticated-orcid":false,"given":"Georgina","family":"Sandoval","sequence":"additional","affiliation":[{"name":"Centro de Investigaci\u00f3n y Asistencia en Tecnolog\u00eda y Dise\u00f1o del Estado de Jalisco (CIATEJ) Av Normalistas 800 44270 Guadalajara Jalisco Mexico"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0429-9620","authenticated-orcid":false,"given":"Francisco","family":"Valero","sequence":"additional","affiliation":[{"name":"Departament d'Enginyeria Quimica Biol\u00f2gica i Ambiental (EE) Universitat Aut\u00f2noma de Barcelona 08193 Bellaterra Barcelona Spain"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3655-8201","authenticated-orcid":false,"given":"Suzana","family":"Ferreira\u2010Dias","sequence":"additional","affiliation":[{"name":"Universidade de Lisboa, Instituto Superior de Agronomia LEAF, Linking Landscape, Environment, Agriculture and Food Tapada da Ajuda 1349\u2010017 Lisbon Portugal"}]}],"member":"311","published-online":{"date-parts":[[2017,10,16]]},"reference":[{"key":"e_1_2_7_2_1","doi-asserted-by":"publisher","DOI":"10.1111\/j.1541-4337.2002.tb00010.x"},{"key":"e_1_2_7_3_1","first-page":"38","volume":"16","author":"Ferreira\u2010Dias S.","year":"2013","journal-title":"Electron. 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