Skip to main content
SpringerLink
Log in

Enhanced Structuring of Fat with Reduced Saturates Using Mixed Molecular Compounds

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

Abstract

Molecular compound formation between multicomponent triacylglyceride (TAG) mixtures was characterized using palm oil mid fraction enriched in sn-1,3-dipalmitoyl-2-oleoylglycerol (cPOP) and a commercial fraction enriched in sn-1,3-dioleyl-2-palmitoylglycerol containing a wide range of TAGs (cOPO). Compound formation occurred at a 1:1 (w/w) ratio of cPOP to cOPO corresponding to an equal parts ratio of two different families of TAGs. One family of TAGs consisted of a grouping of all TAGs composed of a saturated–oleic–saturated (StUSt) positioning of fatty acids. The second family consisted of a grouping of all TAGs composed of all oleic–saturated–oleic and saturated–saturated–oleic fatty acids (UStU, StStU). An increase in solid fat content, peak melting temperature, and crystalline domain size and a change in crystalline microstructure were observed at this ratio corresponding to an overall equality in the amount of cPOP to cOPO. This indicates that it is possible to achieve that same level of solid fat content and hardness as a mixture containing more saturates, simply by slightly decreasing the saturates and substituting an oleic monounsaturated fatty acid containing TAG mixture such that a molecular compound is formed. The increase in full-width at half-maximum indicated a decrease in crystalline order and/or decrease in crystal domain size. The characteristic spherulitic crystalline microstructure of OPO changed to small granular crystals upon addition of cPOP. This discovery may allow for the incorporation of a larger proportion of healthy monounsaturated fats into foods while decreasing the use of saturated and trans fats.

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
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9

Similar content being viewed by others

References

  1. Marangoni AG (2012) Crystallography and polymorphism. In: Wesdorp LH (ed) Structure and Properties of Fat Crystal Networks, 2nd ed. CRC Press, Boca Raton, pp 1–24

  2. Sato K (2001) Crystallization behaviour of fats and lipids—a review. Chem Eng Sci 56:2255–2265. doi:10.1016/S0009-2509(00)00458-9

    Article  CAS  Google Scholar 

  3. Moran DPJ (1963) Phase behavior of some palmito-oleo triglyceride systems. J Appl Chem 13:91–100

    Article  CAS  Google Scholar 

  4. Smith NO (1997) The Gibbs energy basis and construction of melting point diagrams in binary systems. J Chem Educ 74:1080. doi:10.1021/ed074p1080

    Article  CAS  Google Scholar 

  5. Fieldes M, Hartman L (1951) Solidification curves and crystal spacings of binary fatty-acid mixtures. Nature 168:74–75. doi:10.1038/168074b0

    Article  CAS  Google Scholar 

  6. Rossell JB (1967) Phase diagrams of triglyceride systems. Adv Lipid Res 5:353–408

    Article  CAS  Google Scholar 

  7. Shriner RL, Fulton JM, Burks DJ (1931) The ternary system: palmitic, margaric and stearic acids. J Am Chem Soc 225:1494–1499

    Google Scholar 

  8. Minato A, Ueno S, Smith K (1997) Thermodynamic and kinetic study on phase behavior of binary mixtures of POP and PPO forming molecular compound systems. J Phys Chem B 101:3498–3505

    Article  CAS  Google Scholar 

  9. Takeuchi M, Ueno S, Sato K (2002) Crystallization kinetics of polymorphic forms of a molecular compound constructed by SOS (1,3-distearoyl-2-oleoyl-sn-glycerol) and SSO (1,2-distearoyl-3-oleoyl-rac-glycerol). Food Res Int 35:919–926. doi:10.1016/S0963-9969(02)00154-0

    Article  CAS  Google Scholar 

  10. Francis F, Piper SH, Malkin T (1930) The n-fatty acids. In: Proceedings of the Royal Society of London, vol 128. pp 214–252

    Google Scholar 

  11. Slagle FB, Ott E (1933) X-ray studies of mixtures of fatty acids 1,2. J Am Chem Soc 55:4404–4418

    Article  CAS  Google Scholar 

  12. Magne FC, Skau EL (1952) Molecular compound formation between acetamide and long-chain saturated fatty acids. J Am Chem Soc 74:2628–2630. doi:10.1021/ja01130a049

    Article  CAS  Google Scholar 

  13. Engström L (1992) Triglyceride systems forming molecular compounds. Eur J Lipid Sci Technol 94(5):173–181

    Google Scholar 

  14. Ikeda E, Ueno S, Miyamoto R, Sato K (2010) Phase behavior of a binary mixture of 1,3-dipalmitoyl-2-oleoyl-sn-glycerol and 1,3-dioleoyl-2-palmitoyl-sn-glycerol in n-dodecane solution. J Phys Chem B 114:10961–10969. doi:10.1021/jp101821c

    Article  CAS  Google Scholar 

  15. Bayés-García L, Calvet T, Cuevas-Diarte MÀ et al (2011) Heterogeneous microstructures of spherulites of lipid mixtures characterized with synchrotron radiation microbeam X-ray diffraction. Cryst Eng Commun 13:6694. doi:10.1039/c1ce05667k

    Article  Google Scholar 

  16. Zhang L, Ueno S, Miura S, Sato K (2007) Binary phase behavior of 1,3-dipalmitoyl-2-oleoyl-sn-glycerol and 1,2-dioleoyl-3-palmitoyl-rac-glycerol. J Am Oil Chem Soc 84:219–227. doi:10.1007/s11746-006-1034-0

    Article  CAS  Google Scholar 

  17. Zhang L, Ueno S, Sato K et al (2009) Thermal and structural properties of binary mixtures of 1,3-distearoyl-2-oleoyl-glycerol (SOS) and 1,2-dioleoyl-3-stearoyl-sn-glycerol (sn-OOS). J Therm Anal Calorim 98:105–111. doi:10.1007/s10973-009-0451-3

    Article  CAS  Google Scholar 

  18. Wesdorp LH (2005) Mixing behavior in the beta´ and beta modification. In: Marangoni AG (ed) Fat Crystal Networks. CRC Press, Boca Raton, pp 577–579

  19. Shinomiya C (1940) Studies on the organic molecular compounds part III. On the molecular compound-formation of aromatic hydrocarbons with nitro-compounds and with antimony trihalides. Bull Chem Soc Jpn 15(7):259–270

    Article  Google Scholar 

  20. Minato A, Ueno S, Yano J (1997) Thermal and structural properties of sn-1, 3-dipalmitoyl- binary mixtures examined with synchrotron radiation X-ray diffraction. J Am Oil Chem Soc 74:1213–1220

    Article  CAS  Google Scholar 

  21. Sato K, Ueno S, Yano J (1999) Molecular interactions and kinetic properties of fats. Prog Lipid Res 38:91–116. doi:10.1016/S0163-7827(98)00019-8

    Article  CAS  Google Scholar 

  22. Minato A, Yano J, Ueno S et al (1997) FT–IR study on microscopic structures and conformations of POP–PPO and POP–OPO molecular compounds. Chem Phys Lipids 88:63–71. doi:10.1016/S0009-3084(97)00045-5

    Article  CAS  Google Scholar 

  23. Ikeda-Naito E, Hondoh H, Ueno S, Sato K (2014) Mixing phase behavior of 1,3-dipalmitoyl-2-oleoyl-sn-glycerol (POP) and 1,2-dipalmitoyl-3-oleoyl-rac-glycerol (PPO) in n-dodecane solution. J Am Oil Chem Soc 91:1837–1848. doi:10.1007/s11746-014-2534-y

    Article  CAS  Google Scholar 

  24. Boodhoo MV, Kutek T, Filip V, Narine SS (2008) The binary phase behavior of 1,3-dimyristoyl-2-stearoyl-sn-glycerol and 1,2-dimyristoyl-3-stearoyl-sn-glycerol. Chem Phys Lipids 154:7–18. doi:10.1016/j.chemphyslip.2008.04.001

    Article  CAS  Google Scholar 

  25. Talbot G (1995) Fat eutectics and crystallisation. Springer, US

    Book  Google Scholar 

  26. Humphrey KL, Moquin PHL, Narine SS (2003) Phase behavior of a binary lipid shortening system: from molecules to rheology. J Am Oil Chem Soc 80:1175–1182. doi:10.1007/s11746-003-0838-2

    Article  CAS  Google Scholar 

  27. Korver O, Katan MB (2006) The elimination of trans fats from spreads: how science helped to turn an industry around. Nutr Rev 64:275–279. doi:10.1301/nr.2006.jun.275

    Google Scholar 

  28. Stender S, Dyerberg J (2004) Influence of trans fatty acids on health. Ann Nutr Metab 48:61–66. doi:10.1159/000075591

    Article  CAS  Google Scholar 

  29. L’Abbé MR, Stender S, Skeaff CM, Tavella M (2009) Approaches to removing trans fats from the food supply in industrialized and developing countries. Eur J Clin Nutr 63:S50–S67. doi:10.1038/ejcn.2009.14

    Article  Google Scholar 

  30. Haighton AJ (1959) The measurement of the hardness of margarine and fats with cone penetrometers. J Am Oil Chem Soc 36:345–348. doi:10.1007/BF02640051

    Article  CAS  Google Scholar 

  31. Koyano T, Hachiya I, Sato K (1992) Phase behavior of mixed systems of SOS and OSO. J Phys Chem 96:110514–110519

    Article  Google Scholar 

  32. Himawan C, Starov VM, Stapley AGF (2006) Thermodynamic and kinetic aspects of fat crystallization. Adv Colloid Interface Sci 122:3–33

    Article  CAS  Google Scholar 

  33. Scherrer P (1918) Bestimmung der grösse und der inneren struktur von kolloidteilchen mittels röntgenstrahlen. Nachrichten von der Gesellschaft der Wissenschaften zu Göttingen 26:98–100

    Google Scholar 

  34. Wesdorp LH, Meeteren JA van, Jong S de, et al (2012) Liquid-multiple solid phase equilibria in fats theory and experiments In: Marangoni AG (ed) Structure and Properties of Fat Crystal Networks, pp 241–336

Download references

Acknowledgments

The authors would like to thank AarhusKarlhamn (AAK) Sweden AB (SE-374 82 Karlshamn, Sweden) for their kind donation of samples of PMF and OPO used throughout this project.

Author information

Authors and Affiliations

  1. Department of Food Science, University of Guelph, Guelph, ON, Canada

    A. N. Sibbald & A. G. Marangoni

  2. Solazyme Inc., South San Francisco, CA, USA

    J. R. Carney

Authors
  1. A. N. Sibbald
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. J. R. Carney
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. G. Marangoni
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to A. G. Marangoni.

Ethics declarations

Funding sources

The authors acknowledge funding from the Natural Sciences and Engineering Research Council of Canada.

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Sibbald, A.N., Carney, J.R. & Marangoni, A.G. Enhanced Structuring of Fat with Reduced Saturates Using Mixed Molecular Compounds. J Am Oil Chem Soc 93, 1441–1452 (2016). https://doi.org/10.1007/s11746-015-2718-0

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11746-015-2718-0

Keywords

Search

Navigation