Skip to main content
SpringerLink
Log in

Enzymatic Synthesis of Infant Formula Fat Analog Enriched with Capric Acid

  • Original Paper
  • Published:
Journal of the American Oil Chemists' Society

Abstract

A structured lipid (SL) with a substantial amount of palmitic acid at the sn-2 position and enriched with capric acid (C), was produced in two enzymatic interesterification stages by using immobilized lipase, Lipozyme® TL IM (Novozymes North America Inc., Franklinton, NC, USA). The substrates for the reactions were high melting point palm stearin, high oleic sunflower oil and tricaprin. The SL was characterized for total and positional fatty acid profiles, triacylglycerol (TAG) molecular species, free fatty acid content, melting and crystallization profiles. The final SL contained 20.13 mol% of total palmitic acid, of which nearly 40 % was located at the sn-2 position. The total capric acid content was 21.22 mol%, mostly at the sn-1 and sn-3 positions. The predominant TAGs in the SL were oleic–palmitic–oleic, POP and CLC. The melting completion and crystallization onset temperatures of the SL were 27.7 and 6.1 °C, respectively. The yield for the overall reaction was 90 wt%. This SL might be totally or partially used in commercial fat blends for infant formula.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4

Similar content being viewed by others

References

  1. Jensen RG (1989) The lipids of human milk. CRC Press, Boca Raton

    Google Scholar 

  2. Wells JCK (1996) Nutritional considerations in infant formula design. Semin Neonatal 1:19–26

    Article  Google Scholar 

  3. Scott CE (2010) Structured lipid: a functional and fundamental ingredient to more closely matches infant formula to breast milk. Nutrafoods 9:7–13

    Article  CAS  Google Scholar 

  4. Innis SM (1991) Essential fatty acids in growth and development. Prog Lipid Res 30:39–103

    Article  CAS  Google Scholar 

  5. Bracco U (1994) Effect of triglyceride structure on fat absorption. Am J Clin Nutr 60:1002S–1009S

    CAS  Google Scholar 

  6. Lucas A, Quinlan P, Abrams S, Ryan S, Meah S, Lucas PJ (1997) Randomised controlled trial of a synthetic triglyceride milk formula for preterm infants. Arch Dis Child Fetal Neonatal 77:F178–F184

    Article  CAS  Google Scholar 

  7. Tomarelli RM, Meyer BJ, Weaber JR, Bernhart FW (1968) Effect of positional distribution on the absorption of the fatty acids of human milk and infant formulas. J Nutr 95:583–590

    CAS  Google Scholar 

  8. Høy CE, Xu X (2001) Structured triacylglycerols. In: Gunstone FD (ed) Structured and modified lipids. Marcel Dekker, New York, pp 209–239

    Google Scholar 

  9. Akoh CC, Kim BH (2008) Structured Lipids. In: Akoh CC, Min DB (eds) Food lipids. CRC Press, Boca Raton, pp 841–872

    Chapter  Google Scholar 

  10. Zock PL, Gerritsen J, Katan MB (1996) Partial conservation of the sn-2 position of dietary triglycerides in fasting plasma lipids in humans. Eur J Clin Investig 26:141–150

    Article  CAS  Google Scholar 

  11. Zou X, Huang J, Jin Q, Guo Z, Liu Y, Cheong L, Xu X, Wang X (2013) Characterization and oxidative stability of human milk fat substitutes enzymatically produced from palm stearin. J Am Oil Chem Soc 91:481–495

    Article  Google Scholar 

  12. Wang X, Huang J, Jin Q, Song Z, Liu Y, Zou X (2012) Lipase-catalyzed synthesis of human milk fat substitutes from palm stearin in a continuous packed bed reactor. J Am Oil Chem Soc 89:1463–1472

    Google Scholar 

  13. Teichert SA, Akoh CC (2011) Modifications of stearidonic acid soybean oil by enzymatic acidolysis for the production of human milk fat analogues. J Agric Food Chem 59:13300–13310

    Article  CAS  Google Scholar 

  14. Turan D, Yeşilçubuk NS, Akoh CC (2012) Production of human milk fat analogue containing docosahexaenoic and arachidonic acids. J Agric Food Chem 60:4402–4407

    Article  CAS  Google Scholar 

  15. Pande G, Sabir JSM, Baeshen NA, Akoh CC (2013) Enzymatic synthesis of extra virgin olive oil based infant formula fat analogues containing ARA and DHA: one-stage and two-stage syntheses. J Agric Food Chem 61:10590–10598

    Article  CAS  Google Scholar 

  16. Pina-Rodriguez AM, Akoh CC (2009) Synthesis and characterization of a structured lipid from amaranth oil as a partial fat substitute in milk-based infant formula. J Agric Food Chem 57:6748–6756

    Article  CAS  Google Scholar 

  17. Ifeduba EA, Akoh CC (2013) Chemoenzymatic method for producing stearidonic acid concentrates from stearidonic acid soybean oil. J Am Oil Chem Soc 90:1011–1022

    Article  CAS  Google Scholar 

  18. Babayan VK (1988) Medium chain triglycerides. In: Babayan VK, Beare-Rogers J (eds) Dietary fat requirements in health and development. American Oil Chemists’ Society Press, Champaign, pp 73–86

    Google Scholar 

  19. Francois CA, Connor SL, Wander RS, Connor WE (1998) Acute effects of dietary fatty acids on the fatty acids of human milk. Am J Clin Nutr 67:301–308

    CAS  Google Scholar 

  20. López-López A, López-Sabater MC, Campoy-Folgoso C, Rivero-Urgell M, Castellote-Bargalló AI (2002) Fatty acid and sn-2 fatty acid composition in human milk from Granada (Spain) and in infant formulas. Eur J Clin Nutr 56:1242–1254

    Article  Google Scholar 

  21. St-Onge MP, Mayrsohn B, O’Keeffe M, Kissileff HR, Choudhury AR, Laferrère B (2014) Impact of medium and long chain triglycerides consumption on appetite and food intake in overweight men. Eur J Clin Nutr 68:1134–1140

    CAS  Google Scholar 

  22. St-Onge MP, Ross R, Parsons WD, Jones PJ (2003) Medium-chain triglycerides increase energy expenditure and decrease adiposity in overweight men. Obes Res 11:395–402

    Article  CAS  Google Scholar 

  23. Novozymes Biopharma DK A/S (2014) Enzymes for Biocatalysis: for smarter chemical synthesis. http://www.novozymes.com/en/solutions/biopharma/Brochures/Documents/2014-12576-01_Biocatalysis-Product-Sheet-Immobilised-Lipases-2.pdf. Accessed 20 Apr 2015

  24. Pande G, Sabir JSM, Baeshen NA, Akoh CC (2013) Synthesis of infant formula fat analogs enriched with DHA from extra virgin olive oil and tripalmitin. J Am Oil Chem Soc 90:1311–1318

    Article  CAS  Google Scholar 

  25. Official Methods of Analysis of AOAC International (2012) Method 996.01. AOAC Int, Gaitherburg

    Google Scholar 

  26. Luddy FE, Bardford RA, Herb SF, Magidman P, Riemenschneider RW (1964) Pancreatic lipase hydrolysis of triacylglycerides as a semi-micro technique. J Am Oil Chem Soc 41:639–696

    Article  Google Scholar 

  27. Official Methods and Recommended Practices of the American Oil Chemists’ Society (2011) Method Cj 1–94. AOCS, Champaign

    Google Scholar 

  28. Son JM, Lee KT, Akoh CC, Kim MR, Kim MJ, Lee JH (2010) Optimization of tripalmitin-rich fractionation from palm stearin by response surface methodology. J Sci Food Agric 90:1520–1526

    Article  CAS  Google Scholar 

  29. Karupaiah T, Sundram K (2007) Effects of stereospecific positioning of fatty acids in triacylglycerol structures in native and randomized fats: a review of their nutritional implications. Nutr Metab 4:1–17

    Article  Google Scholar 

  30. Kennedy K, Fewtrell MS, Morely R, Abbott R, Quinlan PT, Wells JC, Bindels JG, Lucas A (1999) Double-blind, randomized trial of a synthetic triacylglycerol in formula-fed term infants: effects on stool biochemistry, stool characteristics, and bone mineralization. Am J Clin Nutr 70:920–927

    CAS  Google Scholar 

  31. Yang T, Fruekilde MB, Xu X (2005) Suppression of acyl migration in enzymatic production of structured lipids through temperature programming. Food Chem 92:101–107

    Article  CAS  Google Scholar 

  32. Xu X (2000) Production of specific-structured triacylglycerols by lipase-catalyzed reactions: a review. Eur J Lipid Sci Technol 102:287–303

    Article  CAS  Google Scholar 

  33. Xu X, Skands ARH, Høy CE, Mu H, Balchen S, Adler-Nissen J (1998) Production of specific-structured lipids by enzymatic interesterification: elucidation of acyl migration by response surface design. J Am Oil Chem Soc 75:1179–1186

    Article  CAS  Google Scholar 

  34. Morera S, Castellote AI, Jauregui O, Casals I, López-Sabater MC (2003) Triacylglycerol markers of mature human milk. Eur J Clin Nutr 57:1621–1626

    Article  CAS  Google Scholar 

  35. Mu H, Høy CE (2004) The digestion of dietary triacyglycerols: review. Prog Lipid Res 43:105–133

    Article  CAS  Google Scholar 

  36. Sato K (2005) Polymorphism in fats and oils. In: Bailey’s industrial oil and fat products. Wiley, Hiroshima

  37. Strayer D (2006) Food fats and oils. Institute of Shortening and Edible Oils, Washington DC

    Google Scholar 

  38. Bornaz S, Fanni J, Parmentier M (1994) Limit of the solid fat content modification of butter. J Am Oil Chem Soc 71:1373–1380

    Article  CAS  Google Scholar 

  39. Malcata FX, Reyes HR, García HS, Hill CG Jr, Amundson CH (1992) Kinetics and mechanisms catalyzed by immobilized lipases. Enzyme Microb Technol 14:426–446

    Article  CAS  Google Scholar 

  40. Briand D, Dubreucq E, Galzy P (1994) Enzymatic fatty esters synthesis in aqueous medium with lipase from Candida parapsilosis (Ashford) Langeron and Talice. Biotechnol Lett 16(813):818

    Google Scholar 

  41. Svesson I, Wehtje E, Adlercreutz P, Mattiasson B (1994) Effects of water activity on reaction rates and equilibrium positions in enzymatic esterifications. Biotechnol Bioeng 44:549–556

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Food Science and Technology, University of Georgia, Athens, GA, 30602-2610, USA

    Carlos A. Álvarez & Casimir C. Akoh

  2. Department of Research and Development, Team Foods S.A, Bogotá D.C, 11001000, Colombia

    Carlos A. Álvarez

Authors
  1. Carlos A. Álvarez
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Casimir C. Akoh
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Casimir C. Akoh.

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Álvarez, C.A., Akoh, C.C. Enzymatic Synthesis of Infant Formula Fat Analog Enriched with Capric Acid. J Am Oil Chem Soc 92, 1003–1014 (2015). https://doi.org/10.1007/s11746-015-2662-z

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11746-015-2662-z

Keywords

Search

Navigation