Skip to main content
SpringerLink
Log in

Crystallization Behavior of Diacylglycerol-Rich Oils Produced from Rapeseed Oil

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

Abstract

We examined the crystallization behavior of high-melting fractions in liquid oil containing high concentrations of diacylglycerols (DAG >80%) (hereafter referred to as DAG-rich oil). By differential scanning calorimetry and optical microscopy at moderate cooling rates, crystallization in the DAG-rich oil was detected at around 6 °C. It was found that the crystallization extent increased with decreasing temperatures of crystallization below 0 °C. A gas chromatographic analysis was performed on the crystallized fractions, which were separated by filtration at different periods of isothermal crystallization at 3 °C. The results indicated that at earlier crystallization periods, the concentrations of 1,3-disaturated DAG such as palmitic and stearic acid moieties (15 min) and 1,3-saturated–unsaturated mixed-acid DAG including oleic acid, palmitic, and stearic acid moieties (15 min–3 h) were predominant. However, the concentrations of 1,3-diunsaturated DAG including oleic acid moiety increased after a crystallization period of 6 h. To clarify the sequential crystallization process of DAG, we examined the binary mixing behavior of principal DAG components occurring in the rapeseed-based DAG-rich oil. It was evident that 1,3-disaturated DAG, 1,3-saturated–unsaturated mixed-acid DAG, and 1,3-diunsaturated DAG exhibited immiscible behavior. From these data, basic information on the precipitation processes in DAG-rich oils at chilled temperatures was obtained.

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

Similar content being viewed by others

References

  1. Afoakwa EO, Paterson A, Fowler M (2007) Factors influencing rheological and textural qualities in chocolate––a review. Trends Food Sci Technol 18:290–298

    Article  CAS  Google Scholar 

  2. Bricknell J, Hartel RW (1998) Relation of fat bloom in chocolate to polymorphic transition of cocoa butter. J Am Oil Chem Soc 75:1609–1615

    Article  CAS  Google Scholar 

  3. Hachiya I, Koyano T, Sato K (1989) Seeding effects on solidification behavior of cocoa butter and dark chocolate. II. Physical properties of dark chocolate. J Am Oil Chem Soc 66:1763–1770

    Article  CAS  Google Scholar 

  4. Rousseau D, Marangoni AG (1999) The effects of interesterification on physical and sensory attributes of butterfat and butterfat–canola oil spreads. Food Res Int 31:381–388

    Article  Google Scholar 

  5. Shukla A, Bhaskar AR, Rizvi SSH, Mulvaney SJ (1994) Physicochemical and rheological properties of butter made from supercritically fractionated milk fat. J Dairy Sci 77:45–54

    Article  CAS  Google Scholar 

  6. Swe PZ, Che Man YB, Ghazali HM, Wei LS (1994) Identification of major triglycerides causing the clouding of palm olein. J Am Oil Chem Soc 71:1141–1144

    Article  CAS  Google Scholar 

  7. Swe PZ, Che Man YB, Ghazali HM (1995) Composition of crystals of palm olein formed at room temperature. J Am Oil Chem Soc 72:343–347

    Article  CAS  Google Scholar 

  8. Martini S, Tippetts M (2008) Crystallization behavior and destabilization kinetics of oil in water emulsions. J Am Oil Chem Soc 85:119–128

    Article  CAS  Google Scholar 

  9. Awad T, Sato K (2001) Effects of hydrophobic emulsifier additives on crystallization behavior of palm mid fraction in oil-in-water emulsion. J Am Oil Chem Soc 78:837–842

    Article  CAS  Google Scholar 

  10. Nakajima Y, Nishide T, Sakuma T (2002) Physicochemical properties of diacylglycerol. In: Katsuragi Y, Yasukawa T, Matsuo N, Frickinger BD, Tokimitsu I, Matlock MG (eds) Diacylglycerol oil. AOCS, Illinois, pp 182–196

    Google Scholar 

  11. Murase T, Mizuno T, Omachi T, Onizawa K, Komine Y, Kondo H, Hase T, Tokimitsu I (2001) Dietary diacylglycerol suppresses high fat and high sucrose diet-induced body fat accumulation in C57BL/6J mice. J Lipid Res 42:372–378

    CAS  Google Scholar 

  12. Nagao T, Watanabe H, Goto N, Onizawa K, Taguchi H, Matsuo N, Yasukawa T, Tsushima R, Shimasaki H, Itakura H (2000) Dietary diacylglycerol suppresses accumulation of body fat compared to triacylglycerol in men in a double-blind controlled trial. J Nutr 130:792–797

    CAS  Google Scholar 

  13. Maki KC, Davidson MH, Tsushima R, Matsuo N, Tokimitsu I, Umporowicz DM, Dicklin MR, Foster GS, Ingram KA, Anderson BD, Frost SD, Bell M (2002) Consumption of diacylglycerol oil as part of a reduced-energy diet enhances loss of body weight and fat in comparison with consumption of a triacylglycerol control oil. 76:1230–1236

    CAS  Google Scholar 

  14. Hara K, Onizawa K, Honda H, Otsuji K, Ide T, Murata M (1993) Dietary diacylglycerol-dependent reduction in serum triacylglycerol concentration in rats. Ann Nutr Metab 37:185–191

    Article  CAS  Google Scholar 

  15. Tada N, Watanabe H, Matsuo N, Tokimitsu I, Okazaki M (2001) Dynamics of postprandial remnant-like lipoprotein particles (RLP) in serum after loading of diacylglycerols. Clin Chim Acta 311:109–117

    Article  CAS  Google Scholar 

  16. Taguchi H, Watanabe H, Onizawa K, Nagao T, Gotoh N, Yasukawa T, Tsushima R, Shimasaki H, Itakura H (2000) Double-blind controlled study on the effects of dietary diacylglycerol on postprandial serum and chylomicron triacylglycerol responses in healthy humans. J Am Coll Nutr 19:789–796

    CAS  Google Scholar 

  17. Siew WL, Ng WL (1996) Effect of diacylglycerols on the crystallization of palm oleins. J Sci Food Agric 71:496–500

    Article  CAS  Google Scholar 

  18. Siew WL, Ng WL (1999) Influence of diglycerides on the crystallization of palm oil. J Sci Food Agric 79:722–726

    Article  CAS  Google Scholar 

  19. Wright AJ, Hartel RW, Narine SS, Marangoni AG (2000) The effect of minor components on milk fat crystallization. J Am Oil Chem Soc 77:463–475

    Article  CAS  Google Scholar 

  20. Wright AJ, Marangoni AG (2002) Effect of DAG on milk fat TAG crystallization. J Am Oil Chem Soc 4:395–402

    Article  Google Scholar 

  21. Smith PR, Cebula DJ, Povey MJW (1994) The effect of lauric-based molecules on trilaurin crystallization. J Am Oil Chem Soc 71:1367–1372

    Article  CAS  Google Scholar 

  22. Awad T, Hamada Y, Sato K (2001) Effects of addition of diacylglycerols on fat crystallization in oil-in-water emulsion. Eur J Lipid Sci Technol 103:735–741

    Article  CAS  Google Scholar 

  23. Foubert I, Vanhoutte B, Dewettinck K (2004) Temperature and concentration dependent effect of partial glycerides on milk fat crystallization. Eur J Lipid Sci Technol 106:531–539

    Article  CAS  Google Scholar 

  24. Craven RJ, Lencki RW (2011) Crystallization and polymorphism of 1,3-acyl-palmitoyl-rac-glycerols. J Am Oil Chem Soc 88:1113–1123

    Article  CAS  Google Scholar 

  25. Craven RJ, Lencki RW (2011) Binary phase behavior of diacid 1,3-diacylglycerols. J Am Oil Chem Soc 88:1125–1134

    Article  CAS  Google Scholar 

  26. Craven RJ, Lencki RW (2011) Crystallization, polymorphism, and binary phase behavior of model enantiopure and racemic 1,3-diacylglycerols. Cryst Growth Des 11:1566–1572

    Article  CAS  Google Scholar 

  27. Saberi AH, Lai OM, Vázquez JF (2010) Crystallization kinetics of palm oil in blends with palm-based diacylglycerol. Food Res Int 44:425–435

    Article  Google Scholar 

  28. Cheong LZ, Tan CP, Long K, Yusoff MSA, Lai OM (2009) Physicochemical, textural and viscoelastic properties of palm diacylglycerol bakery margarine during storage. J Am Oil Chem Soc 86:723–731

    Article  CAS  Google Scholar 

  29. Fedotova Y, Lencki RW (2008) The effect of phospholipids on milk fat crystallization behavior. J Am Oil Chem Soc 85:205–212

    Article  CAS  Google Scholar 

  30. Howe RJ, Malkin T (1951) An X-ray and thermal examination of the glycerides. Part VI. The 1:2-diglycerides, and further observations on 1:3-diglycerides. J Chem Soc 2663–2667

  31. Baur FJ, Jackson FL, Kolp DG, Lutton ES (1949) The polymorphism of saturated 1,3-diglycerides. J Am Chem Soc 71:3363–3366

    Article  CAS  Google Scholar 

  32. Kodali RD, Fahey DA, Small DM (1990) Structure and polymorphism of saturated monoacid 1,2-diacyl-sn-glycerols. Biochemistry 29:10771–10779

    Article  CAS  Google Scholar 

  33. Goto M, Honda K, Li D, Small DM (1995) Crystal structure of a mixed chain diacylglycerol, l-stearyl-3-oleoyl-glycerol. J Lipid Res 36:2185–2190

    CAS  Google Scholar 

  34. Li D, Small DM (1993) Physical behavior of the mixed chain diacylglycerol, l-stearyl-2-oleoyl-sn-glycerol: difficulties in chain packing produce marked polymorphism. J Lipid Res 34:1611–1623

    Google Scholar 

  35. Lo SK, Tan CP, Long K, Yusoff M, Lai OM (2008) Diacylglycerol oil properties, processes and products: a review. Food Bioprocess Technol 1:223–233

    Article  Google Scholar 

  36. Koyano T, Hachiya I, Sato K (1992) Phase behavior of mixed system of SOS and OSO. J Phys Chem 96:10514–10520

    Article  CAS  Google Scholar 

  37. Minato A, Ueno S, Yano J, Wang ZH, Seto H, Amemiya Y, Sato K (1996) Synchrotron radiation x-ray diffraction study on phase behavior of PPP–POP binary mixtures. J Am Oil Chem Soc 73:1567–1572

    Article  CAS  Google Scholar 

  38. Boodhoo MV, Bouzidi L, Narine SS (2009) The binary phase behavior of 1,3-dipalmitoyl-2-stearoyl-sn-glycerol and 1,2-dipalmitoyl-3-stearoyl-sn-glycerol. Chem Phys Lipids 160:11–32

    Article  CAS  Google Scholar 

  39. Kellens M, Meeussen W, Hammersley A, Reynaers H (1991) Synchrotron radiation investigations of the polymorphic transitions of saturated monoacid triglycerides. Part 2: Polymorphism study of a 50:50 mixture of tripalmitin and tristearin during crystallization and melting. Chem Phys Lipids 58:145–158

    Article  CAS  Google Scholar 

  40. Takeuchi M, Ueno S, Floeter E, Sato K (2002) Binary phase behavior of 1,3-distearoyl-2-oleoyl-sn-glycerol (SOS) and 1,3-distearoyl-2-linoleoyl-sn-glycerol (SLS). J Am Oil Chem Soc 79:627–632

    Article  CAS  Google Scholar 

  41. Daubert BF, Lutton ES (1947) X-ray diffraction analyses of synthetic unsaturated monoacid diglycerides. J Am Chem Soc 69:1449–1451

    Article  CAS  Google Scholar 

  42. Shannon RJ, Fenerty J, Hamilton RJ, Padley FB (1992) The polymorphism of diglycerides. J Sci Food Agric 60:405–417

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Kao Corporation, Global R & D, Health Care Food, Sumida-ku, Japan

    Katsuyoshi Saitou, Yuki Mitsui, Masao Shimizu, Naoto Kudo & Yoshihisa Katsuragi

  2. Graduate School of Biosphere Science, Hiroshima University, Higashi-Hiroshima, Japan

    Kiyotaka Sato

Authors
  1. Katsuyoshi Saitou
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Yuki Mitsui
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Masao Shimizu
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Naoto Kudo
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Yoshihisa Katsuragi
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Kiyotaka Sato
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Katsuyoshi Saitou.

About this article

Cite this article

Saitou, K., Mitsui, Y., Shimizu, M. et al. Crystallization Behavior of Diacylglycerol-Rich Oils Produced from Rapeseed Oil. J Am Oil Chem Soc 89, 1231–1239 (2012). https://doi.org/10.1007/s11746-012-2014-1

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11746-012-2014-1

Keywords

Search

Navigation