[en] This study aims to evaluate the potential of applying enzymatic interesterification (EIE) to produce new healthy zero-trans high vitaminic content margarine fats, based on rapeseed oil (RO) only, with a specific focus on process-induced contaminants: the dialkylketones. Three blends made of RO and fully hydrogenated rapeseed oil (60:40, 70:30 and 80:20 wt:wt%) were considered. Compositional and melting properties, polymorphic behavior, appearance and textural characteristics were compared before and after interesterification. Interesterification improved both functional and textural characteristics. Enzymatic interesterification produced fats which presented similar triacylglycerol profile and physicochemical properties as the chemically interesterified one (CIE), however, preserving more tocopherols and without forming dialkylketones (process-induced contaminants). On the contrary, it was shown that after CIE, dialkylketones were formed: C18:1- C18:1 and C18:1- C18 chain-lengths being the major ones, and interestingly, their amount increased with the unsaturation in the blends. Our results indicate the great potential of enzymatic interesterification to produce new healthy fats entirely based on rapeseed oil. This study provides valuable information for the food industry, showing EIE as cutting-edge sustainable technology.
Disciplines :
Food science
Author, co-author :
Danthine, Sabine ; Université de Liège - ULiège > TERRA Research Centre > Smart Technologies for Food and Biobased Products (SMARTECH)
AOCS. 2017. Official methods and recommended practices of the American Oil Chemist's Society, 7th ed. Champaign: AOCS Press.
BfR Recommendation XXXVI. 2017. Paper and board for food contact. Berlin, Germany: German Federal Institute for Risk Assessment.
Costales-Rodríguez R, Gibon V, Verhé R, De Greyt W. 2009. Chemical and enzymatic interesterification of a blend of palm stearin: soybean oil for low trans-margarine formulation. Journal of the American Oil Chemists' Society 86(7): 681-697.
Cui H, Li J, Xu X, et al. 2022. Enzymatic interesterification of beef tallow/coconut oil blends to produce a superior margarine base stock. International Journal of Food Science and Technology 57: 908-919.
Danthine S. 2012. Physicochemical and structural properties of compound dairy fat blends. Food Research International 48(1): 187-195.
Danthine S, Deroanne C. 2003. Physical and textural characteristics of hydrogenated low-erucic acid rapeseed oil and low-erucic acid rapeseed oil blends. Journal of the American Oil Chemists' Society 80(2): 109-114.
Danthine S, De Clercq N, Dewettinck K, Gibon V. 2014a. Monitoring batch lipase catalyzed interesterification of palm oil and fractions by differential scanning calorimetry. J Therm Anal Calorim 115: 2219-2229. https://doi. org/10. 1007/s10973-014-3645-2.
Danthine S, Lefebure E, Trinh HN, Blecker C. 2014b. Effect of palm oil enzymatic interesterification on physicochemical and structural properties of mixed fat blends. Journal of the American Oil Chemists' Society 91(9): 1477-1487. https://doi. org/10. 1007/s11746-014-2494-2.
De Clercq N, Danthine S, Tuyet Nguyen M, Gibon V, Dewettinck K. 2012. Enzymatic interesterification of palm oil and fractions: monitoring the degree of interesterification using different methods. Journal of the American Oil Chemists' Society 89: 219-229. https://doi. org/10. 1007/s11746-011-1905-x.
Detry R, Van Hoed V, Sterckx J, et al. 2021. Physicochemical properties of palm oil-based puff pastry model margarines related to their baking performance in long-term storage. Eur J Lipid Sci Technol 123: 2000155. https://doi. org/10. 1002/ejlt. 202000155.
Gibon V. 2012. Palm oil and palm kernel oil refining and fractionation technology. In: Lai O-M, Tan C-P, Akoh CC, eds. Palm oil: production, processing, characterization, and uses. Urbana, IL: AOCS Press, pp. 329-375. https://doi. org/10. 1016/B978-0-9818936-9-3. 50015-0.
Gibon V. 2021. Enzymatic interesterification for zero trans margarines and shortening: A sustainable alternative to chemical. In: Fundamentals of Oilseed Extraction, and Oils & Fats Processing andApplicationTechnology ForAmerica, Europe, Middle East and Africa business. Online conferences. April 7-9, 2021.
Gibon V, Kellens M. 2014. Latest developments in chemical and enzymatic interesterification for commodity oils and specialty fats. In: Kodali DR, ed. Trans fats: replacement solutions. Urbana, IL: AOCS Press, pp. 153-185.
Gunstone F, Gunstone FD. 2006. Vegetable sources of lipids. In: Gunstone FD, ed. Modifying lipids for use in food. Woodhead Publishing Series in Food Science, Technology and Nutrition, pp. 11-27.
IUPAC. 1987. Standard methods for the analysis of oils. Fats and derivatives. 7th edn. London: Blackwell Scientific Publications.
Karabulut I, Turan S, Ergin G. 2004. Effects of chemical interesterification on solid fat content and slipmelting point of fat/oil blends. European Food Research and Technology 218(3): 224-229.
Kato Y, Watanabe S. 2022. Separation and quantification of dialkyl ketones. Results in Chemistry 4: 100277.
Lefébure E, Ronkart S, Brostaux Y, Béra F, Blecker C, Danthine S. 2013. Investigation of the influence of processing parameters on physicochemical properties of puff pastry margarines using surface response methodology. LWT-Food Science and Technology 51: 225-232.
Li Y, Zhao J, Xie X, Zhang Z, Zhang N, Wang Y. 2018. A low trans margarine fat analog to beef tallow for healthier formulations: optimization of enzymatic interesterification using soybean oil and fully hydrogenated palm oil. Food Chemistry 255: 405-413. https://doi. org/10. 1016/j. foodchem. 2018. 02. 086.
Mariani C, Bellan G. 2011. Individuazione di oli e grassi interesterificati conmetodologie diverse. Rivista Italiana delle Sostanze Grasse 88: 172-181.
Mascrez S, Danthine S, Purcaro G. 2021. Microwave-assisted saponification method followed by solid-phase extraction for the characterization of sterols and dialkyl Ketones in fats. Foods 10: 445.
Mozaffarian D, Aro A, Willett WC. 2009. Health effects of trans-fatty acids: experimental and observational evidence. European Journal of Clinical Nutrition 63: S5-S21. https://doi. org/10. 1038/sj. ejcn. 1602973.
Nekrasov P, Gudz I, Nekrasov I, Berezka T. 2020. Optimizing the parameters of the production process of fat systems with a minimum content of trans-isomers ISSN 0321-4095. Voprosy Khimii i Khimicheskoi Tekhnologii (3): 128-133.
Noor Lida HMD, Ali ARM. 1998. Physico-chemical characteristics of palm-based oil blends for the production of reduced fat spreads. Journal of the American Oil Chemists' Society 75(11): 1625-1631.
Pang M, Ge Y, Cao L, Cheng J, Jiang S. 2019. Physicochemical properties, crystallization behavior and oxidative stabilities of enzymatic interesterified fats of beef tallow, palm stearin and camellia oil blends. Journal of Oleo Science 68(2): 131-139. https://doi. org/10. 5650/jos. ess18201.
Piravi-Vanak Z. 2020. Cold pressed colza oil. In: Ramadan MF, ed. Cold pressed oils. Green technology, bioactive compounds, functionality, and applications. Elsevier Inc., pp 429-437.
Ribeiro AP, Grimaldi R, Gioielli L, Goncalves LAG. 2009. Zero trans fats from soybean oil and fully hydrogenated soybean oil: physico-chemical properties and food applications. Food Research International 42: 401-410.
Ruan X, Zhu X, Xiong H, Wang S, Bai C, Zhao Q. 2014. Characterization of zero-trans margarine fats produced from camellia seed oil, palm stearin and coconut oil using enzymatic interesterification strategy. International Journal of Food Science and Technology 49: 91-97.
Salgarella NI, Forte E, Cardenia V. 2021. Formation of dialkyl ketones (DAKs) in fats as related to different deodorization conditions in refining processing. In: Poster Presented at 18th Euro Fed Lipid Congress, 18-21 October 2021-online and Expo.
Santoro V, Baiocchi C, Dal Bello F, et al. 2018. Formation of byproducts during chemical interesterification of lipids. Detection and characterization of dialkyl ketones by non-aqueous reversedphase liquid chromatography-high resolution mass spectrometry and gas chromatography-mass spectrometry. J Chromatogr A 1581-1582: 63-70.
Segura N, Jachmanián I. 2020. Zero-trans fats by enzymatic interesterification of blends beef tallow/rice bran oil. OCL 27: 4. https://doi. org/10. 1051/ocl/2019052.
Shi C, Chang M, Liu R, Jin Q, Wang X. 2015. Trans-free shortenings through the interesterification of rice bran stearin, fully hydrogenated soybean oil and coconut oil. International Journal of Food Engineering 11(4): 467-77. https://doi. org/10. 1515/ijfe-2014-0279.
Simone dos Santos C, Fortes Kanup R, Albuquerque M, et al. 2020. Effect of enzymatic interesterification on the textural and nutritional properties of a probiotic table spread containing milk fat. LWT-Food Science and Technology 124: 109129.
Sivakanthan S, Madhujith T. 2020. Current trends in applications of enzymatic interesterification of fats and oils: A review. LWT-Food Science and Technology 132: 109880.
Stanley JC. 2009. Stearic or palmitic acid as a substitute for trans fatty acids? Lipid Technol 7: 54-57.
T'Zand I, Bouwer S, Bhaggan K, Schmid U. 2009. Loders Croklaan B. V. Process. WO 2009/012982 A2
U. S. Food and Drug Administration (FDA). 2018. Code of Federal Regulations (CFR), Title 21, Part 176. 120-Indirect Food Additives, Paper and Paperboard Components, Alkyl ketene dimers. Silver Spring, MD, USA: U. S. Food and Drug Administration. UE regulation: règlement (UE) 2019/649 de la commission du 24 avril 2019.
van Rooijen M., Mensink R. 2020. Palmitic acid versus stearic acid: effects of interesterification and intakes on cardiometabolic risk markers-A systematic review. Nutrients 12: 615. https://doi. org/10. 3390/nu12030615.
Verhe R, Van Hoed V, De Greyt W. 2006. Detection of alkyl ketones during chemical interesterification of lipids. In: Proceedings of the Paper Presented at 97th AOCS Annual Meeting & Expo, St-Louis, MO, USA, 3 May 2006.
WHO. 2018. WHO plan to eliminate industrially-produced trans-fatty acids from global food supply. https://www. who. int/news-room/detail/14-05-2018-who-plan-to-eliminate-industrially-producedtrans-fatty-acids-from-global-food-supply (last consult: August 30th, 2021).
Wijendran V, Hayes KC. 2004. Dietary n-6 and n-3 fatty acid balance and cardiovascular health. Annu Rev Nutr 24: 597-615.
Wilczeka MM, Olszewskib R, Krupieniczc A. 2017. Trans-fatty acids and cardiovascular disease: urgent need for legislation. Cardiology 138: 254-258. https://doi. org/10. 1159/000479956.
Wirkowska-Wojdya M, Brys J, Gorska A, Ostrowska-Ligeza E. 2016. Effect of enzymatic interesterification on physiochemical and thermal properties of fat used in cookies. LWT-Food Science and Technology 74: 99-105. https://doi. org/10. 1016/j. lwt. 2016. 07. 040.
Yu D, Qi X, Jiang Y, et al. 2018. Preparation of margarine stock rich in naturally bioactive components by enzymatic interesterification. Journal of Oleo Science 67(1): 29-37. https://doi. org/10. 5650/jos. ess17076.
Zhang Z, Lee WJ, Wang Y. 2020. Evaluation of enzymatic interesterification in structured triacylglycerols preparation: A concise review and prospect. Critical Reviews in Food Science and Nutrition 22: 1-15. https://doi. org/10. 1080/10408398. 2020. 1793725.
Zhang Z, Shim YY, Ma X, Wang HHY. 2018. Solid fat content and bakery characteristics of interesterified beef tallow-palm mid fraction based margarines. RSC Adv 8: 12390. https://doi. org/10. 1039/c8ra00769a.
Zhao S, Hu J, Zhu Z, et al. 2014. Characteristics and feasibility of trans-free plastic fats through lipozyme TL IM-catalyzed interesterification of palm stearin and Akebia trifoliata variety Australis seed oil. Journal of Agriculture and Food Chemistry 62(14): 3293-3300. https://doi. org/10. 1021/jf500267e.
