Skip to main content
    • Aa
    • Aa
  • Access
  • Cited by 48
  • Cited by
    This article has been cited by the following publications. This list is generated based on data provided by CrossRef.

    Afonso, Milessa Silva Lavrador, Maria Silvia Ferrari Koike, Marcia Kiyomi Cintra, Dennys Esper Ferreira, Fabiana Dias Nunes, Valeria Sutti Castilho, Gabriela Gioielli, Luiz Antonio Paula Bombo, Renata Catanozi, Sergio Caldini, Elia Garcia Damaceno-Rodrigues, Nilsa Regina Passarelli, Marisa Nakandakare, Edna Regina and Lottenberg, Ana Maria 2016. Dietary interesterified fat enriched with palmitic acid induces atherosclerosis by impairing macrophage cholesterol efflux and eliciting inflammation. The Journal of Nutritional Biochemistry, Vol. 32, p. 91.

    Gallier, Sophie Acton, Dennis Garg, Manohar and Singh, Harjinder 2016. Natural and processed milk and oil body emulsions: Bioavailability, bioaccessibility and functionality. Food Structure,

    Gao, Feng Yang, Shuo and Birch, John 2016. Physicochemical characteristics, fatty acid positional distribution and triglyceride composition in oil extracted from carrot seeds using supercritical CO2. Journal of Food Composition and Analysis, Vol. 45, p. 26.

    Lopes, Thiago I.B. Ribeiro, Marilene D.M.M. Ming, Chiu C. Grimaldi, Renato Gonçalves, Lireny A.G. and Marsaioli, Anita J. 2016. Comparison of the regiospecific distribution from triacylglycerols after chemical and enzymatic interesterification of high oleic sunflower oil and fully hydrogenated high oleic sunflower oil blend by carbon-13 nuclear magnetic resonance. Food Chemistry, Vol. 212, p. 641.

    Thilakarathna, S. H. Rogers, M. Lan, Y. Huynh, S. Marangoni, A. G. Robinson, L. E. and Wright, A. J. 2016. Investigations of in vitro bioaccessibility from interesterified stearic and oleic acid-rich blends. Food Funct., Vol. 7, Issue. 4, p. 1932.

    Trullàs, C. Fontanillas, R. Tres, A. and Sala, R. 2016. Fatty acid digestibility in gilthead sea bream fed diets containing native, re-esterified or acid vegetable oils. Aquaculture Nutrition, p. n/a.

    Wang, Xiaosan Wang, Tong Spurlock, Michael E. and Wang, Xingguo 2016. Effects of triacylglycerol structure and solid fat content on fasting responses of mice. European Journal of Nutrition, Vol. 55, Issue. 4, p. 1545.

    Aljewicz, Marek and Cichosz, Grażyna 2015. The effect of probiotic Lactobacillus rhamnosus HN001 on the in vitro availability of minerals from cheeses and cheese-like products. LWT - Food Science and Technology, Vol. 60, Issue. 2, p. 841.

    Ciapaite, Jolita van den Berg, Sjoerd A. Houten, Sander M. Nicolay, Klaas Willems van Dijk, Ko and Jeneson, Jeroen A. 2015. Fiber-type-specific sensitivities and phenotypic adaptations to dietary fat overload differentially impact fast- versus slow-twitch muscle contractile function in C57BL/6J mice. The Journal of Nutritional Biochemistry, Vol. 26, Issue. 2, p. 155.

    Havlicekova, Zuzana Jesenak, Milos Banovcin, Peter and Kuchta, Milan 2015. Beta-palmitate – a natural component of human milk in supplemental milk formulas. Nutrition Journal, Vol. 15, Issue. 1,

    Imran, Muhammad and Nadeem, Muhammad 2015. Triacylglycerol composition, physico-chemical characteristics and oxidative stability of interesterified canola oil and fully hydrogenated cottonseed oil blends. Lipids in Health and Disease, Vol. 14, Issue. 1,

    Janssens, Sharon Heemskerk, Mattijs M. van den Berg, Sjoerd A. van Riel, Natal A. Nicolay, Klaas Willems van Dijk, Ko and Prompers, Jeanine J. 2015. Effects of low-stearate palm oil and high-stearate lard high-fat diets on rat liver lipid metabolism and glucose tolerance. Nutrition & Metabolism, Vol. 12, Issue. 1,

    Kadhum, Abdul Amir H. and Shamma, M. Najeeb 2015. Edible Lipids Modification Processes: A Review. Critical Reviews in Food Science and Nutrition, p. 00.

    Masquio, D. C. L. de Piano, A. Campos, R. M. S. Sanches, P. L. Carnier, J. Corgosinho, F. C. Netto, B. D. M. Carvalho-Ferreira, J. P. Oyama, L. M. Oller do Nascimento, C. M. Tock, L. de Mello, M. T. Tufik, S. and Dâmaso, A. R. 2015. Reduction in saturated fat intake improves cardiovascular risks in obese adolescents during interdisciplinary therapy. International Journal of Clinical Practice, Vol. 69, Issue. 5, p. 560.

    Misan, Vanessa Estato, Vanessa de Velasco, Patricia Coelho Spreafico, Flavia Brasil Magri, Tatiana dos Santos, Raísa Magno de Araújo Ramos Fragoso, Thaiza Souza, Amanda S. Boldarine, Valter Tadeu Bonomo, Isabela T. Sardinha, Fátima L.C. Oyama, Lila M. Tibiriçá, Eduardo and Tavares do Carmo, Maria das Graças 2015. Interesterified fat or palm oil as substitutes for partially hydrogenated fat during the perinatal period produces changes in the brain fatty acids profile and increases leukocyte–endothelial interactions in the cerebral microcirculation from the male offspring in adult life. Brain Research, Vol. 1616, p. 123.

    Pacheco, Consuelo Crapiste, Guillermo H. and Carrín, María E. 2015. Study of acyl migration during enzymatic interesterification of liquid and fully hydrogenated soybean oil. Journal of Molecular Catalysis B: Enzymatic, Vol. 122, p. 117.

    Ruiz-Lopez, Noemi Stubhaug, Ingunn Igapharraguerre, Ignacio Rimbach, Gerald and Menoyo, David 2015. Positional Distribution of Fatty Acids in Triacylglycerols and Phospholipids from Fillets of Atlantic Salmon (Salmo Salar) Fed Vegetable and Fish Oil Blends. Marine Drugs, Vol. 13, Issue. 7, p. 4255.

    Speranza, Paula Badan Ribeiro, Ana Paula Cunha, Rosiane Lopes Macedo, Juliana Alves and Macedo, Gabriela Alves 2015. Influence of emulsion droplet size on antimicrobial activity of interesterified Amazonian oils. LWT - Food Science and Technology, Vol. 60, Issue. 1, p. 207.

    Trullàs, C. Fontanillas, R. Tres, A. and Sala, R. 2015. Vegetable re-esterified oils in diets for rainbow trout: Effects on fatty acid digestibility. Aquaculture, Vol. 444, p. 28.

    Wang, Xiaosan Zou, Wanzhen Sun, Xuemei Zhang, Yu Wei, Liying Jin, Qingzhe and Wang, Xingguo 2015. Chemoenzymatic synthesis of 1,3-dioleoyl-2-palmitoylglycerol. Biotechnology Letters, Vol. 37, Issue. 3, p. 691.


Triacylglycerol structure and interesterification of palmitic and stearic acid-rich fats: an overview and implications for cardiovascular disease

  • Sarah E. E. Berry (a1)
  • DOI:
  • Published online: 01 May 2009

The position of fatty acids in the TAG molecule (sn-1, sn-2 and sn-3) determines the physical properties of the fat, which affects its absorption, metabolism and distribution into tissues, which may have implications for the risk of CHD. The TAG structure of fats can be manipulated by the process of interesterification, which is of increasing commercial importance, as it can be used to change the physical characteristics of a fat without the generation of trans-fatty acids. Interesterified fats rich in long-chain SFA are commercially important, but few studies have investigated their health effects. Evidence from animal and human infant studies suggests that TAG structure and interesterification affect digestibility, atherogenicity and fasting lipid levels, with fats containing palmitic and stearic acid in the sn-2 position being better digested and considered to be more atherogenic. However, chronic studies in human adults suggest that TAG structure has no effect on digestibility or fasting lipids. The postprandial effects of fats with differing TAG structure are better characterised but the evidence is inconclusive; it is probable that differences in the physical characteristics of fats resulting from interesterification and changes in TAG structure are key determinants of the level of postprandial lipaemia, rather than the position of fatty acids in the TAG. The present review gives an overview of TAG structure and interesterified palmitic and stearic acid-rich fats, their physical properties and their acute and chronic effects in human adults in relation to CHD.

  • View HTML
    • Send article to Kindle

      To send this article to your Kindle, first ensure is added to your Approved Personal Document E-mail List under your Personal Document Settings on the Manage Your Content and Devices page of your Amazon account. Then enter the ‘name’ part of your Kindle email address below. Find out more about sending to your Kindle.

      Note you can select to send to either the or variations. ‘’ emails are free but can only be sent to your device when it is connected to wi-fi. ‘’ emails can be delivered even when you are not connected to wi-fi, but note that service fees apply.

      Find out more about the Kindle Personal Document Service.

      Triacylglycerol structure and interesterification of palmitic and stearic acid-rich fats: an overview and implications for cardiovascular disease
      Available formats
      Send article to Dropbox

      To send this article to your Dropbox account, please select one or more formats and confirm that you agree to abide by our usage policies. If this is the first time you use this feature, you will be asked to authorise Cambridge Core to connect with your Dropbox account. Find out more about sending content to Dropbox.

      Triacylglycerol structure and interesterification of palmitic and stearic acid-rich fats: an overview and implications for cardiovascular disease
      Available formats
      Send article to Google Drive

      To send this article to your Google Drive account, please select one or more formats and confirm that you agree to abide by our usage policies. If this is the first time you use this feature, you will be asked to authorise Cambridge Core to connect with your Google Drive account. Find out more about sending content to Google Drive.

      Triacylglycerol structure and interesterification of palmitic and stearic acid-rich fats: an overview and implications for cardiovascular disease
      Available formats
Corresponding author
Corresponding author: Dr Sarah Berry, fax +44 20 7848 4185, email
Linked references
Hide All

This list contains references from the content that can be linked to their source. For a full set of references and notes please see the PDF or HTML where available.

1M Lefevre , PM Kris-Etherton , G Zhao , . (2004) Dietary fatty acids, hemostasis, and cardiovascular disease risk. J Am Diet Assoc 104, 410419.

2FM Sacks & M Katan (2002) Randomized clinical trials on the effects of dietary fat and carbohydrate on plasma lipoproteins and cardiovascular disease. Am J Med 113, Suppl. 9B, 13S24S.

11AG Marangoni & D Rousseau (1995) Engineering triacylglycerols: the role of interesterification. Trends Food Sci Technol 6, 329335.

12H Lavery (1958) Differential thermal analysis of fats. II. Melting behavior of some pure glycerides. J Am Oil Chem Soc 35, 418422.

14D Mozaffarian , MB Katan , A Ascherio , . (2006) Trans fatty acids and cardiovascular disease. N Engl J Med 354, 16011613.

23SE Berry , R Woodward , C Yeoh , . (2007) Effect of interesterification of palmitic acid-rich triacylglycerol on postprandial lipid and factor VII response. Lipids 42, 315323.

24SM Innis , R Dyer & CM Nelson (1994) Evidence that palmitic acid is absorbed as sn-2 monoacylglycerol from human milk by breast-fed infants. Lipids 29, 541545.

27BC Mortimer , MA Kenrick , DJ Holthouse , . (1992) Plasma clearance of model lipoproteins containing saturated and polyunsaturated monoacylglycerols injected intravenously in the rat. Biochim Biophys Acta 1127, 6773.

28BC Mortimer , WJ Simmonds , CA Joll , . (1989) The effect of added monoacylglycerols on the removal from plasma of chylomicron-like emulsions injected intravenously in rats. Biochim Biophys Acta 1002, 359364.

29BC Mortimer , WJ Simmonds , SJ Cockman , . (1990) The effect of monostearoylglycerol on the metabolism of chylomicron-like lipid emulsions injected intravenously in rats. Biochim Biophys Acta 1046, 4656.

30KM Botham (2008) Oxidation of chylomicron remnants and vascular dysfunction. Atheroscler Suppl 9, 5761.

37W Smink , WJ Gerrits , R Hovenier , . (2008) Fatty acid digestion and deposition in broiler chickens fed diets containing either native or randomized palm oil. Poult Sci 87, 506513.

38A Lucas , P Quinlan , S Abrams , . (1997) Randomised controlled trial of a synthetic triglyceride milk formula for preterm infants. Arch Dis Child Fetal Neonatal Ed 77, F178F184.

39VP Carnielli , IH Luijendijk , JB van Goudoever , . (1996) Structural position and amount of palmitic acid in infant formulas: effects on fat, fatty acid, and mineral balance. J Pediatr Gastroenterol Nutr 23, 553560.

42RG Jensen (1999) Lipids in human milk. Lipids 34, 12431271.

43D Kritchevsky (1995) Fatty acids, triglyceride structure, and lipid metabolism. J Nutr Biochem 6, 172178.

44DM Small (1991) The effects of glyceride structure on absorption and metabolism. Annu Rev Nutr 11, 413434.

45EA Decker (1996) The role of stereospecific saturated fatty acid positions on lipid nutrition. Nutr Rev 54, 108110.

46A Bonanome & SM Grundy (1988) Effect of dietary stearic acid on plasma cholesterol and lipoprotein levels. N Engl J Med 318, 12441248.

48Y Shahkhalili , E Duruz & K Acheson (2000) Digestibility of cocoa butter from chocolate in humans: a comparison with corn-oil. Eur J Clin Nutr 54, 120125.

51JT Snook , S Park , G Williams , . (1999) Effect of synthetic triglycerides of myristic, palmitic, and stearic acid on serum lipoprotein metabolism. Eur J Clin Nutr 53, 597605.

52SS Tuomasjukka , MH Viitanen & HP Kallio (2009) Regio-distribution of stearic acid is not conserved in chylomicrons after ingestion of randomised, stearic acid-rich fat in a single meal. J Nutr Biochem (epublication ahead of print version 4 February 2009).

57HR Jung , SM Turner , RA Neese , . (1999) Metabolic adaptations to dietary fat malabsorption in chylomicron-deficient mice. Biochem J 343, 473478.

58D Kritchevsky , SA Tepper , SC Chen , . (2000) Cholesterol vehicle in experimental atherosclerosis. 23. Effects of specific synthetic triglycerides. Lipids 35, 621625.

59D Kritchevsky , SA Tepper , A Kuksis , . (2000) Cholesterol vehicle in experimental atherosclerosis. 22. Refined, bleached, deodorized (RBD) palm oil, randomized palm oil and red palm oil. Nutr Res 20, 887892.

60D Kritchevsky , SA Tepper , G Bises , . (1982) Experimental atherosclerosis in rabbits fed cholesterol-free diets. Atherosclerosis 41, 279284.

61D Kritchevsky & SA Tepper (1977) Cholesterol vehicle in experimental atherosclerosis. Part 15. Randomized butter and randomized lard. Atherosclerosis 27, 339345.

62PJ van Jaarsveld , CM Smuts & AS Benadé (2002) Effect of palm olein oil in a moderate-fat diet on plasma lipoprotein profile and aortic atherosclerosis in non-human primates. Asia Pac J Clin Nutr 11, Suppl. 7, S424S432.

63JB Keogh , JA Grieger , M Noakes , . (2005) Flow-mediated dilatation is impaired by a high-saturated fat diet but not by a high-carbohydrate diet. Arterioscler Thromb Vasc Biol 25, 12741279.

64M Sarabi , B Vessby , J Millgard , . (2001) Endothelium-dependent vasodilation is related to the fatty acid composition of serum lipids in healthy subjects. Atherosclerosis 156, 349355.

65NJ de Fouw , GA Kivits , PT Quinlan , . (1994) Absorption of isomeric, palmitic acid-containing triacylglycerols resembling human milk fat in the adult rat. Lipids 29, 765770.

67MB Reena & BR Lokesh (2007) Hypolipidemic effect of oils with balanced amounts of fatty acids obtained by blending and interesterification of coconut oil with rice bran oil or sesame oil. J Agric Food Chem 55, 1046110469.

69PM Kris-Etherton , J Derr , DC Mitchell , . (1993) The role of fatty acid saturation on plasma lipids, lipoproteins, and apolipoproteins: I. Effects of whole food diets high in cocoa butter, olive oil, soybean oil, dairy butter, and milk chocolate on the plasma lipids of young men. Metabolism 42, 121129.

70WE Connor , DT Witiak , DB Stone , . (1969) Cholesterol balance and fecal neutral steroid and bile acid excretion in normal men fed dietary fats of different fatty acid composition. J Clin Invest 48, 13631375.

77AB Christophe , WF De Greyt , JR Delanghe , . (2000) Substituting enzymatically interesterified butter for native butter has no effect on lipemia or lipoproteinemia in man. Ann Nutr Metab 44, 6167.

78DB Zilversmit (1979) Atherogenesis: a postprandial phenomenon. Circulation 60, 473485.

79RA Vogel , MC Corretti & GD Plotnick (1997) Effect of a single high-fat meal on endothelial function in healthy subjects. Am J Cardiol 79, 350354.

80GJ Miller (1998) Postprandial lipaemia and haemostatic factors. Atherosclerosis 141, Suppl. 1, S47S51.

81SH Gianturco & WA Bradley (1999) Pathophysiology of triglyceride-rich lipoproteins in atherothrombosis: cellular aspects. Clin Cardiol 22, Suppl. 6, II7II14.

82JR Patsch , G Miesenbock , T Hopferwieser , . (1992) Relation of triglyceride metabolism and coronary artery disease. Studies in the postprandial state. Arterioscler Thromb 12, 13361345.

86KM Yli-Jokipii , US Schwab , RL Tahvonen , . (2003) Chylomicron and VLDL TAG structures and postprandial lipid response induced by lard and modified lard. Lipids 38, 693703.

91DM Robinson , NC Martin , LE Robinson , . (2009) Influence of interesterification of a stearic acid-rich spreadable fat on acute metabolic risk factors. Lipids 44, 1726.

94DT Stein , BE Stevenson , MW Chester , . (1997) The insulinotropic potency of fatty acids is influenced profoundly by their chain length and degree of saturation. J Clin Invest 100, 398403.

96M Kjalke , A Silveira , A Hamsten , . (2000) Plasma lipoproteins enhance tissue factor-independent factor VII activation. Arterioscler Thromb Vasc Biol 20, 18351841.

Recommend this journal

Email your librarian or administrator to recommend adding this journal to your organisation's collection.

Nutrition Research Reviews
  • ISSN: 0954-4224
  • EISSN: 1475-2700
  • URL: /core/journals/nutrition-research-reviews
Please enter your name
Please enter a valid email address
Who would you like to send this to? *