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Interesterified fats are oils where the fatty acids have merely been moved from one triglyceride molecule to another. Interesterification does not alter the fatty acids. This is generally done in order to modify the melting point, slow rancidification and create an oil more suitable for deep frying or making margarine with good taste and low content of saturated fatty acids. This is unlike partial hydrogenation which produces trans fatty acids.

Chemistry[edit]

Fats such as soybean oil consist mainly of various triglycerides which are made up of a glycerol backbone esterified to three fatty acid molecules. The triglycerides contain a mixture of saturated, monounsaturated and polyunsaturated fatty acids. Interesterification is carried out by blending the desired oils and than rearranging the fatty acids over the glycerol backbone with, for instance the help of Lipase enzymes. [1]Polysunsaturated fatty acids decrease the melting point of fats significantly. A triglyceride containing three saturated fatty acids is generally solid at room temperature and not very desirable for many applications. Rearranging these tryglycerides with oils containing unsaturated fatty acids lowers the melting point and creates fats with properties better suited for high quality products. In addition blending interesterified oils with liquid oils allows the reduction in saturated fats in many trans fatty free food products. The interesterified fats can be separated through controlled crystallization or fractionation. [2]

A triglyceride with a PUFA (linolenic acid) at the sn-2 position which is replaced by a saturated fatty acid (stearic acid) via interesterification.

In polyunsaturated fats, the PUFA is commonly found at the middle position (sn2) on the glycerol. Stearic acid is not usually found at sn2 in vegetable oils used in the human diet.[1]

Health effects[edit]

In most vegetable dietary fats palmitic (C16:0) and stearic acids (C18:0) mainly occupy the 1- and 3-positions of the triacylglycerol molecule, whereas an unsaturated fatty acid such as oleic acid or linoleic acid usually occupies the 2-position. In animal fats this is not the case. Interesterification of vegetable oils will enhance the amount of saturated fatty acids at the 2-position. Fatty acids at the 2-position are biologically different from fatty acids at the 1 and 3 position because they are handled differently during digestion and metabolism and a major scientific question is whether there are health effects following from this. As consequence the area has been well researched.

In studies addressing the health effects of interesterification as such, a diet high in interesterified fat should be compared with a diet high in a non-interesterified fat with the same fatty acid composition. If the two diets show similar changes in the resulting blood lipid profiles (i.e. not different from each other), this indicates that interesterification has no effect on metabolism or biological effects. Conversely, effects of interesterification can not be properly addressed if the interesterified fat and the non-interesterified fat being compared have different fatty acid compositions.

Zock et al [3] compared the effects of an IE test fat with 40% C16:0 on the 2-position with a non-interesterified test fat with only 6.5 % C16:0 on the 2-position in a 3-week diet study. Despite the very high intakes and the marked difference in positional distribution, no statistically significant effects on fasting blood lipids were observed in the group as a whole. Nestel et al[4] examined the effects of an IE fat blend with 25% C16:0 on the 2-position with a native fat blend with only 9% C16:0 on the 2-position. Again, despite a high intake level and the clear difference in positional distribution of the fats fed, no effects were observed on fasting blood lipids. Meijer and Weststrate [5] examined the effects of interesterification, using a ‘real’ hardstock as applied in foods. The control was the same fat blend with a similar fatty acid composition, but not interesterified. The IE fat blend contained more C16:0 on the 2-position (18%) than the control blend (7%). None of the fasting levels of blood lipids measured after 3 weeks showed any change related to treatment of the fat blend. Fasting glucose level was also not affected.

In 1970 Grande et al [6] used interesterification to prepare a blend of fats and oils mimicking the fatty acid composition of cocoa butter. No difference between the interesterified fat blend and cocoa butter was observed in levels of total cholesterol in fasting blood. Recently, Sundram et al. [7] compared the effects of three types of fat: native palm olein, a blend with partially hydrogenated soybean oil and an interesterified mixture of oils. They concluded that both the IE blend and the partially hydrogenated fat blend decrease the fasting LDL/HDL-cholesterol ratio, indicating an adverse effect on CVD risk. Sundram et al also found that fasting plasma glucose levels were higher after 4 weeks on the interesterified fat than after the other diets. As was pointed out in a letter to the Editor by Destaillats et al [8] a major limitation of the Sundram study is that the diets differed in overall fatty acid composition.The interesterified fat had 30% more saturated and 57% less mono-unsaturated fatty acids than the untreated palm olein. The direction of the effects on blood lipids are in line with what can be predicted based on these differences in fatty acid content between the study diets (Mensink 2003) [9] Another recent study by Berry et al [10]compared shea butter (3% C18:0 on the 2-position) and interesterified shea butter (23% C18:0 on the 2-position), while keeping overall fatty acid composition of the diets constant. This study found no effects of interesterification on fasting levels of blood lipids, glucose and insulin. This is line with a number of other human intervention studies. [11][12][13][14]

Christophe et al[15][16]have studied the effect of interesterification of butter oil. In a small pilot study [15], they observed an 11% lower blood total cholesterol level after interesterification. In a larger, better designed study [16], no effect was seen of substituting enzymatically interesterified butter oil for butter.

In summary almost all longer term diet studies and acute post meal studies do not show any adverse health effects attributable to interesterification.

References[edit]

  1. ^ a b Instute of Shortenings and Edible oils (2006). "Food Fats and oils" (PDF). Retrieved 2009-02-19. {{cite web}}: Cite has empty unknown parameter: |1= (help)
  2. ^ Kellens, Marc (2000). "Interesterification Process Conditions" (PDF). Retrieved 2007-01-29.
  3. ^ Zock PJ, de Vries JHM, de Fouw NJ, Katan MB (1995), "Positional distribution of fatty acids in dietary triglycerides: effects on fasting blood lipoprotein concentrations in humans.", Am J Clin Nutr, 61 (1): 48–551, doi:10.1093/ajcn/61.1.48, hdl:1871/11621, PMID 7825538{{citation}}: CS1 maint: multiple names: authors list (link)
  4. ^ Nestel PJ, Noakes M, Belling GB; et al. (1995), "Effect on plasma lipids of interesterifying a mix of edible oils.", Am J Clin Nutr, 62 (5): 950–55, doi:10.1093/ajcn/62.5.950, PMID 7572740 {{citation}}: Explicit use of et al. in: |author= (help)CS1 maint: multiple names: authors list (link)
  5. ^ Meijer GW, Weststrate JA (1997), "Interesterification of fats in margarine: effect on blood lipids, blood enzymes and hemostasis parameters.", Eur J Clin Nutr, 51 (8): 527–34, doi:10.1038/sj.ejcn.1600437, S2CID 10919060
  6. ^ Grande F, Anderson JT, Keys A. (1970), "Comparison of effects of palmitic and stearic acids in the diet on serum cholesterol in man.", Am J Clin Nutr, 23 (9): 1184–93, doi:10.1093/ajcn/23.9.1184, PMID 5450836{{citation}}: CS1 maint: multiple names: authors list (link)
  7. ^ Sundram K, Karupaiah T, Hayes K. (2007). "Stearic acid-rich interesterified fat and trans-rich fat raise the LDL/HDL ratio and plasma glucose relative to palm olein in humans" (PDF). Nutr Metab. 4: 3. doi:10.1186/1743-7075-4-3. PMID 17224066. S2CID 17115311. Retrieved 2007-01-19.{{cite journal}}: CS1 maint: multiple names: authors list (link) CS1 maint: unflagged free DOI (link)
  8. ^ Destaillats F, Moulin J, Bezelgues J-B (2007), "Letter to the editor: healthy alternatives to trans fats", Nutr and Metab, 4: 10, doi:10.1186/1743-7075-4-10, PMC 1867814, PMID 17462099{{citation}}: CS1 maint: multiple names: authors list (link) CS1 maint: unflagged free DOI (link)
  9. ^ Mensink RP, Zock, PL, kester AD, Katan MB. (2003), "Effects of dietary fatty acids and carbohydrates on the ratio of serum total to HDL cholesterol and on serum lipids and apolipoproteins: a meta-analysis of 60 controlled trials.", Am J Clin Nutr, 77 (5): 1146–1155, doi:10.1093/ajcn/77.5.1146, PMID 12716665{{citation}}: CS1 maint: multiple names: authors list (link)
  10. ^ Berry SEE, Miller GJ, Sanders TAB. (2007), "The solid fat content of stearic acid-rich fats determines their postprandial effects.", Am J Clin Nutr, 85 (6): 1486–94, doi:10.1093/ajcn/85.6.1486, PMID 17556683{{citation}}: CS1 maint: multiple names: authors list (link)
  11. ^ Zampelas A, Williams CM, Morgan LM; et al. (1994), "The effect of triacylglycerol fatty acids positional distribution on postprandial plasma metabolite and hormone responses in normal adult men.", Brit J Nutr, 71 (3): 401–10, doi:10.1079/BJN19940147, PMID 8172869 {{citation}}: Explicit use of et al. in: |author= (help)CS1 maint: multiple names: authors list (link)
  12. ^ Yli-Jokipii K, Kallio H, Schwab U; et al. (2001), "Effects of palm oil and transesterified palm oil on chylomicron and VLDL triacylglycerol structures and postprandial lipid response.", J Lip Res, 42 (10): 1618–25, PMID 11590218 {{citation}}: Explicit use of et al. in: |author= (help)CS1 maint: multiple names: authors list (link)
  13. ^ Berry SEE, Woodward R, Yeoh C, Miller GJ, Sanders TAB. (2007), "Effect of interesterification of palmitic-acid rich tryacylglycerol on postprandial lipid and factor VII response", Lipids, 42 (4): 315–323, doi:10.1007/s11745-007-3024-x, PMID 17406926, S2CID 3986807{{citation}}: CS1 maint: multiple names: authors list (link)
  14. ^ Summers LKM, Fielding BA, Herd SL; et al. (1999), "Use of structured triacylglycerols containing predominantly stearic and oleic acids to probe early events in metabolic processing of dietary fat", J Lip Res, 40 (10): 1890–98, PMID 10508209 {{citation}}: Explicit use of et al. in: |author= (help)CS1 maint: multiple names: authors list (link)
  15. ^ a b Christophe A, Matthys F, Geers R, Verdonk G. (1978), "Nutritional studies with randomised butter. Cholesterolemic effects of butter oil and randomised butter oil in man.", Arch Intern Biophys Biochim, 86: 413–15{{citation}}: CS1 maint: multiple names: authors list (link)
  16. ^ a b Christophe AB, De Greyt WF, Delanghe JR, Huyghebaert AD. (2000), "Substituting enzymically interesterified butter for native butter has no effect on lipemia or lipoproteinemia in man", Annals of Nutr and Metab, 44 (2): 61–67, doi:10.1159/000012822, PMID 10970994, S2CID 22276158{{citation}}: CS1 maint: multiple names: authors list (link)

See also[edit]

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