Isomerización cis-trans de ácidos grasos insaturados en aceites comestibles para preparar grasas trans

Autores/as

DOI:

https://doi.org/10.3989/gya.0225181

Palabras clave:

Ácido p-toluenosulfínico, Ácidos grasos trans, Grasas trans, Isomerización cis-trans, Manteca comestible

Resumen


Las grasas trans, ácidos grasos insaturados con al menos un doble enlace en la configuración trans, han recibido muchas atenciones en oleoquímica y seguridad. En este trabajo, se ha llevado a cabo con éxito la isomerización cis-trans de ácidos grasos insaturados en aceites comestibles usando mediante un método simple y barato utilizando ácido p-toluenosulfínico como catalizador. Los efectos del tiempo de reacción, la temperatura, la carga del catalizador, la cantidad de agua y los antioxidantes en la isomerización cis-trans se han investigado sistemáticamente. Los resultados indicaron que la cantidad de agua (0–20% en peso) y antioxidante (0–200 mg/ kg) no tuvo un efecto significativo sobre la isomerización cis-trans. Los productos finales (grasas trans) de la reacción de isomerización cis-trans se caracterizaron por GC y React IR. El rendimiento en dobles enlaces trans de la manteca isomerizada puede alcanzar el 79,6% tras calentar a 100 ºC durante 90 minutos sin cambiar tanto la posición de los dobles enlaces como el grado de insaturación. Además, este método tan útil se ha aplicado a diferentes aceites vegetales (por ejemplo, oliva, semilla de camelia, maíz, sésamo, girasol y soja) y casi se forma alrededor del 80.0% de ácidos grasos trans, lo que demuestra ser un método prometedor para proporcionar productos grasos trans para investigaciones relacionadas en la química del aceite y los alimentos.

Descargas

Los datos de descargas todavía no están disponibles.

Citas

Akin G, Arslan FN, Elmas SNK, Yilmaz I. 2018. Cold-pressed pumpkin seed (Cucurbita pepo L.) oils from the central Anatolia region of Turkey: Characterization of phytosterols, squalene, tocols, phenolic acids, carotenoids and fatty acid bioactive compounds. Grasas Aceites 69, e232. https://doi.org/10.3989/gya.0668171

Belitz HD, Grosch W. 1999. Food Chemistry. Springer Verlag.

Cizmeci M, Musavi A, Kayahan M, Tekin A. 2005. Monitoring of hydrogenation with various catalyst ratios. J. Am. Oil Chem. Soc. 82, 925–929.

Duffy PE, Quinn SM, Roche HM, Evans P. 2006. Synthesis of trans-vaccenic acid and cis-9- trans-11-conjugated linoleic acid. Tetrahedron 62, 4838–4843.

Elbadawi SMA, Ahmad EEM, Mariod AA, Mathaus B. 2017. Effects of thermal processing on physicochemical properties and oxidative stability of Balanities aegyptiaca kernels and extracted oil. Grasas Aceites 68, e184.

Farag RS, Elagaimy MAS, Elhakeem BSA. 2010. Effects of mixing canola and palm oils with sunflower oil on the formation of trans fatty acids during frying. Food & Nutr. Sci. 01, 24–29.

Ferreri C, Costantino C, Perrotta L, Landi L, Mulazzani QG, Chatgilialoglu C. 2001. cis-trans Isomerization of polyunsaturated fatty acid residues in phospholipids catalyzed by thiyl radicals. J. Am. Chem. Soc. 123, 4459– 4468.

Garcia C, Duby C, Catheline D, Toral PG, Bernard L, Legrand P, Rioux V. 2017. Synthesis of the suspected trans-11, cis- 13 conjugated linoleic acid isomer in ruminant mammary tissue by FADS3-catalyzed ?13-desaturation of vaccenic acid. J. Dairy Sci. 100, 783–796.

Geißler C, Brede O, Reinhardt J. 2003. cis-trans Isomerization of unsaturated fatty acids during ?-irradiation of barley grains. Radiat. Phys. Chem. 67, 105–113.

Gibson TW, Strassburger P. 1976. Sulfinic acid catalyzed isomerization of olefins. J Org. Chem. 41, 767–770.

Hulshof KFAM, Erp-Baart MAV, Antttolainen M, Becker W, Church SM, Couet C, Hermann-Kunz E, Kesteloot H, Leth T, Martins I, Moreiras O, Moschandreas J, Pizzoferrato L, Rimestad AH, Thorgeirsdottir H, Amelsvoort JMMV, Aro A, Kafatos AG, Lanzmann-Petithory D, Poppel GV. 1999. Intake of fatty acids in western Europe with emphasis on trans fatty acids: the TRANSFAIR study. Eur. J. Clin. Nutr. 53, 143–157

Iida H, Itoh D, Minowa S, Yanagisawa A, Igarashi A. 2015. Hydrogenation of soybean oil over various platinum catalysts: Effects of support materials on trans fatty acid levels. Catal. Commun. 62, 1–5. https://doi.org/10.1016/j.catcom.2014.12.025

Kala ALA. 2012. cis-, trans- and Saturated fatty acids in selected hydrogenated and refined vegetable oils in the Indian market. J. Am. Oil Chem. Soc. 89, 1813–1821.

Kuhnt K, Degen C, Jahreis G. 2015. Evaluation of the impact of ruminant trans fatty acids on human health: Important aspects to consider. Crit. Rev. Food Sci. 4, 1964–1980.

Kurt C. 2018. Variation in oil content and fatty acid composition of sesame accessions from different origins. Grasas Aceites 69, e241.

Lemaitre RN, King IB, Mozaffarian D, Sotoodehnia D, Rea TD, Kuller LH, Tracy RP, Siscovick DS. 2006. Plasma phospholipid trans fatty acids, fatal ischemic heart disease and sudden cardiac death in older adults: the cardiovascular health study. Circulation 114, 209–215. https://doi.org/10.1161/CIRCULATIONAHA.106.620336

Li A, Ha YM, Wang F, Li WM, Li QP. 2012. Determination of thermally induced trans-fatty acids in soybean oil by attenuated total reflectance fourier transform infrared spectroscopy and gas chromatography analysis. J. Agric. Food Chem. 60, 10709–10713. https://doi.org/10.1021/jf3033599

Liu W, Lu GH. 2017. Partial hydrogenation of sunflower oil-derived FAMEs catalyzed by the efficient and recyclable palladium nanoparticles in polyethylene glycol. J. Oleo Sci. 66, 1161–1168.

Mozaffarian D, Katan MB, Ascherio A, Stampfer MJ, Willett WC. 2006. Trans fatty acids and cardiovascular disease. New Engl. J. Med. 354, 1601–1613.

Phillips KM, Ruggio DM, Howe JC, Leheska JM, Smith SB, Engle T, Rasor AS, Conley NA. 2010. Preparation and characterization of control materials for the analysis of conjugated linoleic acid and trans-vaccenic acid in beef. Food Res. Int. 43, 2253–2261.

Snyder JM, Scholfield CR. 1982. cis-trans Isomerization of unsaturated fatty acids with p-toluenesulfinic acid. J. Am. Oil Chem. Soc. 59, 469–470.

Trattner S, Becker W, Wretling S, Öhrvik V, Mattisson I. 2015. Fatty acid composition of Swedish bakery products with emphasis on trans-fatty acids. Food Chem. 175, 423–430.

Tsuzuki W, Matsuoka A, Ushida K. 2010. Formation of trans fatty acids in edible oils during the frying and heating process. Food Chem. 123, 976–982.

Tzeng YZ, Hu CH. 2014. Radical-induced cis-trans isomerization of fatty acids: a theoretical study. J. Phys. Chem. A 118, 4554–4564.

Vahmani P, Rolland DC, Gzyl KE, Dugan MER. 2016. Non-conjugated cis/trans, 18:2 in beef fat are mainly ?-9 desaturation products of trans -18:1 isomers. Lipids 51, 1427–1433.

Publicado

2018-09-30

Cómo citar

1.
Liu W, Lu GH. Isomerización cis-trans de ácidos grasos insaturados en aceites comestibles para preparar grasas trans. Grasas aceites [Internet]. 30 de septiembre de 2018 [citado 4 de agosto de 2026];69(3):e268. Disponible en: https://grasasyaceites.revistas.csic.es/index.php/grasasyaceites/article/view/1736

Número

Sección

Investigación