Grasas y Aceites, Vol 69, No 3 (2018)

Cis-trans isomerization of unsaturated fatty acids in edible oils to prepare trans fat


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

W. Liu
Lipid Chemistry, College of Food Science and Technology, Henan University of Technology, China
orcid http://orcid.org/0000-0003-1706-1208

G. H. Lu
Lipid Chemistry, College of Food Science and Technology, Henan University of Technology, China
orcid http://orcid.org/0000-0002-7586-7448

Abstract


Trans fats, unsaturated fatty acids with at least one double bond in the trans configuration, have received a great amount of attention in the field of oleo chemistry and safety. In this work, the cis-trans isomerization of unsaturated fatty acids in edible oils has been successfully developed using simple and cheap p-toluenesulfinic acid as catalyst. The effects of reaction time, temperature, catalyst loading, and the amounts of water and antioxidants on the cis-trans isomerization have been systematically investigated. The results indicate that the amount of water (0–20 wt %) and antioxidants (0–200 mg/kg) had no significant effect on this cis-trans isomerization of unsaturated fatty acids in edible oils. The final products (trans fats) from the cis-trans isomerization reaction were characterized by both GC and React IR. The yield of trans double bonds from the isomerized fat can reach 79.6% after heating at 100 oC for 90 min without changing either the location of the double bonds or the degree of unsaturation. In addition, this convenient method has been applied to various vegetable oils (e.g., olive oil, camellia seed oil, corn oil, sesame oil, sunflower oil and soybean oil) and nearly 80.0% yields of TFA were generated, which shows a promising method to provide trans-fat products for research related to oleo and food chemistry.

Keywords


cis-trans Isomerization; Edible fat; p-Toluenesulfinic acid; trans Fats; trans Fatty acids

Full Text:


HTML PDF XML

References


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.




Copyright (c) 2018 Consejo Superior de Investigaciones Científicas (CSIC)

Creative Commons License
This work is licensed under a Creative Commons Attribution 4.0 International License.


Contact us grasasyaceites@ig.csic.es

Technical support soporte.tecnico.revistas@csic.es