Journal of the American Oil Chemists' Society

, Volume 86, Issue 3, pp 297–300 | Cite as

Polymorphic Behavior of Structured Fats Including Stearic Acid and ω-3 Polyunsaturated Fatty Acids

  • Kiyotaka Sato
  • Tomoe Kigawa
  • Satoru Ueno
  • Naohiro Gotoh
  • Shun Wada
Letter to the Editor

Dear Sir,

It has widely been recognized that long-chain ω-3 polyunsaturated fatty acids (ω-3 PUFAs) such as α-linolenic acid (ALA), eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) play critical roles in human health [1, 2, 3]. Compared with chemical and nutritional studies of the ω-3 PUFAs, their physical properties have so far not been clarified (except for ALA) [4]. This is mainly because the ω-3 PUFAs are liquid at ambient temperatures in a form of free fatty acid (FFA), as their low melting points are low (−11 °C for ALA, −54 °C for EPA and −44 °C for DHA). Therefore, research to determine the physical properties of lipid materials, that are more significant in solid state or liquid-crystalline states rather than in a liquid state, has been limited [5, 6, 7]. Wijesundera et al. recently studied chemical and physical properties of triacylglycerols (TAGs), in which palmitic acid, oleic acid and DHA are esterified at various glycerol carbon positions [8, 9]. Quite...


Differential Scanning Calorimetric Ricinoleic Acid Glycerol Carbon Differential Scanning Calorimetric Heating Detailed Molecular Structure 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.


  1. 1.
    Cunnane SC (2003) Problems with essential fatty acids: time for a new paradigm? Prog Lipid Res 42:544–568CrossRefGoogle Scholar
  2. 2.
    Schmitz G, Ecker J (2008) The opposing effects of n-3 and n-6 fatty acids. Prog Lipid Res 47:147–155CrossRefGoogle Scholar
  3. 3.
    Hamazaki T, Hamazaki K (2008) Fish oil and aggression or hostility. Prog Lipid Res 47:221–232CrossRefGoogle Scholar
  4. 4.
    Ueno S, Miyazaki A, Yano J, Furukawa Y, Suzuki M, Sato K (2000) Polymorphism of linoleic acid (cis-9, cis-12-Octadecadienoic acid) and a-linolenic acid (cis-9, cis-12, cis-15-Octadecatrienoic acid). Chem Phys Lipids 107:169–178CrossRefGoogle Scholar
  5. 5.
    Serebrennikova GA, Mitrofanov TK, Kraevski AA, Sarychev IK, Preobrazhenski NA (1961) Total synthesis of triglycerides of soybean oil. Doklady Chem 140:1008–1011 (S-ALA-S, 36C)Google Scholar
  6. 6.
    Haraldsson GG, Halldorsson A, Kulas E (2000) Chemoenzymatic synthesis of structured triacylglycerols containing eicosapentaenoic and docosahexaenoic acids. J Am Oil Chem Soc 77:1139–1145 (S-DHA-S 35-35.5C) (S-EPA-S 33.5-34C)CrossRefGoogle Scholar
  7. 7.
    Adlof RO, List GR (2003) Synthesis and analysis of symmetrical and nonsymmetrical disaturated/monounsaturated triacylglycerols. J Agric Food Chem 51:2096–2099 (S-ALA-S 36.5C)CrossRefGoogle Scholar
  8. 8.
    Fraser BH, Perlmutter P, Wijesundera C (2006) Practical syntheses of triacylglycerol regioisomers containing long-chain polyunsaturated fatty acids. J Am Oil Chem Soc 84:11–21CrossRefGoogle Scholar
  9. 9.
    Wijesundera C, Ceccato C, Watkins P, Fagan P, Fraser B, Thienthong N, Perlmutter P (2008) Docosahexaenoic acid is more stable to oxidation when located at the sn-2 position of triacylglycerol compared to sn-1(3). J Am Oil Chem Soc 85:543–548CrossRefGoogle Scholar
  10. 10.
    Sato K, Arishima T, Wang ZH, Ojima K, Sagi N, Mori H (1989) Polymorphism of POP and SOS. I. Occurrence and polymorphic transformation. J Am Oil Chem Soc 66:664–674CrossRefGoogle Scholar
  11. 11.
    Takeuchi M, Ueno S, Yano J, Floeter E, Sato K (2000) Polymorphic transformation of 1,3-distearoyl-sn-linoleoyl-glycerol. J Am Oil Chem Soc 77:1243–1249CrossRefGoogle Scholar
  12. 12.
    Mykhaylyk OO, Smith KW, Martin CM, Ryan AJ (2007) Structural models of metastable phase occurring during the crystallization process of saturated/unsaturated triacylglycerols. J Appl Cryst 40:S297–S302CrossRefGoogle Scholar
  13. 13.
    Rousset P, Rappaz M (1996) Crystallization kinetics of the pure triacylglycerols: glycerol-1,3-dipalmitate-2-oleate, glycerol-1-palmitate-2-oleate-3-stearate, and glycerol-1,3-distearate-2-oleate. J Am Oil Chem Soc 73:1051–1057CrossRefGoogle Scholar
  14. 14.
    Boubekri K, Yano J, Ueno S, Sato K (1999) Polymorphic Transformations in SRS (sn-1,3-distearoyl-2-ricinoleyl glycerol). J Am Oil Chem Soc 76:949–955CrossRefGoogle Scholar

Copyright information

© AOCS 2009

Authors and Affiliations

  • Kiyotaka Sato
    • 1
  • Tomoe Kigawa
    • 1
  • Satoru Ueno
    • 1
  • Naohiro Gotoh
    • 2
  • Shun Wada
    • 2
  1. 1.Graduate School of Biosphere ScienceHiroshima UniversityHigashi-HiroshimaJapan
  2. 2.Department of Food Science and TechnologyTokyo University of Marine Science and TechnologyTokyoJapan

Personalised recommendations