The binary phase behavior of 1,3-dilauroyl-2-stearoyl-sn-glycerol and 1,2-dilauroyl-3-stearoyl-sn-glycerol

Chemistry and Physics of Lipids

Volumn 163, Issue 6, 2010, Pages 607-629

  Bouzidi, Laziz ^a   Boodhoo, Marc V ^a   Kutek, Tomas ^b   Filip, Vladimir ^b   Narine, Suresh S ^a  

^a TRENT UNIVERSITY   (Canada)

^b INSTITUTE OF CHEMICAL TECHNOLOGY   (Czech Republic)

Author keywords

Binary phase behavior; Crystal network; Crystallization; Differential scanning calorimetry; Microstructure; Polymorphism; Powder X ray diffraction; Symmetrical and asymmetrical triacylglycerols

Indexed keywords

1,2 DILAUROYL 3 STEAROYL SN GLYCEROL; 1,3 DILAUROYL 2 STEAROYL SN GLYCEROL; UNCLASSIFIED DRUG; 1,2-DILAUROYL-3-STEAROYLGLYCEROL; 1,3-DILAUROYL-2-STEAROYLGLYCEROL; GLYCEROL; TRIACYLGLYCEROL;

ARTICLE; COOLING; CRYSTALLIZATION; DIFFERENTIAL SCANNING CALORIMETRY; FAT CONTENT; HARDNESS; HUMAN; MELTING POINT; MOLECULAR INTERACTION; PHYSICAL PHASE; PRIORITY JOURNAL; THERMODYNAMICS; ANALOGS AND DERIVATIVES; CHEMISTRY; KINETICS; PHASE TRANSITION; X RAY DIFFRACTION;

CALORIMETRY, DIFFERENTIAL SCANNING; CRYSTALLIZATION; GLYCEROL; KINETICS; PHASE TRANSITION; TRIGLYCERIDES; X-RAY DIFFRACTION;

EID: 77954218249     PISSN: 00093084     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chemphyslip.2010.05.002     Document Type: Article

References (93)

1. M. Abes, L. Bouzidi, and S.S. Narine Crystallization and phase behavior of 1,3-propanediol esters II. 1,3-Propanediol distearate/1,3-propanediol dipalmitate (SS/PP) and 1,3-propanediol distearate/1,3-propanediol dimyristate (SS/MM) binary systems Chem. Phys. Lipids 150 2007 89 108
2. M. Abes, L. Bouzidi, and S.S. Narine Crystallization and phase behavior of fatty acid esters of 1,3 propanediol III: 1,3 propanediol dicaprylate/1,3 propanediol distearate (CC/SS) and 1,3 propanediol dicaprylate/1,3 propanediol dipalmitate (CC/PP) binary systems Chem. Phys. Lipids 151 2008 110 124
3. P.H. Bentley, and W. McCrae Efficient synthesis of symmetrical 1,3-diglycerides J. Org. Chem. 35 1970 2082 2083
4. M.V. Boodhoo, L. Bouzidi, and S.S. Narine The binary phase behavior of 1,3-dicaproyl-2-stearoyl-sn-glycerol and 1,2-dicaproyl-3-stearoyl-sn-glycerol Chem. Phys. Lipids 157 2009 21 39
5. M.V. Boodhoo, L. Bouzidi, and S.S. Narine The binary phase behavior of 1, 3-dipalmitoyl-2-stearoyl-sn-glycerol and 1, 2-dipalmitoyl-3-stearoyl-sn- glycerol Chem. Phys. Lipids 160 2009 11 32
6. M.V. Boodhoo, K.L. Humphrey, and S.S. Narine Relative hardness of fat crystal networks using force displacement curves Int. J. Food Prop. 12 2009 129 144
7. M.V. Boodhoo, T. Kutek, V. Filip, and S.S. Narine The binary phase behavior of 1,3-dimyristoyl-2-stearoyl-sn-glycerol and 1,2-dimyristoyl-3- stearoyl-sn-glycerol Chem. Phys. Lipids 154 2008 7 18
8. L. Bouzidi, M. Boodhoo, K.L. Humphrey, and S.S. Narine Use of first and second derivatives to accurately determine key parameters of DSC thermographs in lipid crystallization studies Thermochim. Acta 439 2005 94 102
9. W.L. Bragg, and E.J. Williams The effect of thermal agitation on atomic arrangement in alloys Proc. Roy. Soc. 145 1934 699 730
10. D.V. Chandran, and R.K. Bhatnagar A method for synthesis of α-monoricinolein J. Am. Oil Chem. Soc. 45 1968 581 582
11. Y.P. Chen, M. Tang, and J.C. Kuo Solid-liquid equilibria for binary mixtures of N-phenylacetamide with 4-aminoacetophenone, 3-hydroxyacetophenone and 4-hydroxyacetophenone Fluid Phase Equilib. 232 2005 182 188
12. M.C. Costa, M.P. Rolemberg, L.A.D. Boros, M.A. Krahenbuhl, M.G. de Oliveira, and A.J.A. Meirelles Solid-liquid equilibrium of binary fatty acid mixtures J. Chem. Eng. Data 52 2007 30 36
13. J. Dafler Polymorphism behavior in fully hydrogenated mono-acid triglycerides J. Am. Oil Chem. Soc. 54 1977 249 254
14. S.D. de Jong, and T.C. van Soest Crystal-structures and melting points of saturated triglycerides in β-2 phase Acta Crystallogr. Sect. B: Struct. Commun. 34 1978 1570 1583
15. J.M. Deman X-ray diffraction spectroscopy in the study of fat polymorphism Food Res. Int. 25 1992 471 476
16. P. Elisabettini, G. Lognay, A. Desmedt, C. Culot, N. Istasse, E. Deffense, and F. Durant Synthesis and physicochemical characterization of mixed diacid triglycerides that contain elaidic acid J. Am. Oil Chem. Soc. 75 1998 285 291
17. L. Engstrom Triglyceride systems forming molecular compounds Fett Wiss. Technol.-Fat Sci. Technol. 94 1992 173 181
18. D.A. Fahey, D.M. Small, D.R. Kodali, D. Atkinson, and T.G. Redgrave Structure and polymorphism of 1,2-dioleoyl-3-acyl-sn-glycerols-3-layered and 6-layered structures Biochemistry 24 1985 3757 3764
19. K. Fontell X-ray diffraction by liquid crystals G.W. Gray, P.A. Winsor, Liquid Crystals and Plastic Crystals: Physico-Chemical Properties and Methods of Investigation 1974 Wiley & Sons Inc. New York
20. P. Garidel, C. Johann, and A. Blume The calculation of heat capacity curves and phase diagrams based on regular solution theory J. Therm. Anal. Calorim. 82 2005 447 455
21. B.S. Ghotra, S.D. Dyal, and S.S. Narine Lipid shortenings: a review Food Res. Int. 35 2002 1015 1048
22. V. Gibon, F. Durant, and C. Deroanne Polymorphism and intersolubility of some palmitic, stearic and oleic triglycerides-PPP, PSP and POP J. Am. Oil Chem. Soc. 63 1986 1047 1055
23. S.S. Godavarthy, R.L. Robinson, and K.A.M. Gasem An improved structure-property model for predicting melting-point temperatures Ind. Eng. Chem. Res. 45 2006 5117 5126
24. S.S. Godavarthy, R.L. Robinson, and K.A.M. Gasem Improved structure-property relationship models for prediction of critical properties Fluid Phase Equilib. 264 2008 122 136
25. M. Goto, D.R. Kodali, D.M. Small, K. Honda, K. Kozawa, and T. Uchida Single-crystal structure of a mixed-chain triacylglycerol-1,2-dipalmitoyl-3- acetyl-sn-glycerol Proc. Natl. Acad. Sci. U.S.A. 89 1992 8083 8086
26. F.D. Gunstone, and F.B. Padley Lipid Technologies and Applications 1997 Marcel Dekker New York p. 848
27. J. Hagemann Thermal behavior and polymorphism of acylglycerols N. Garti, K. Sato, Crystallization and Polymorphism of Fats and Fatty Acids 1988 Marcel Dekker New York 9 98
28. W.A. Harrison Electronic Structure and the Properties of Solids: The Physics of the Chemical Bond 1980 W.H. Freeman and Company San Francisco p. 476
29. J.H. Hildebrand Solubility XII. Regular solutions J. Am. Chem. Soc. 51 1929 66 80
30. C. Himawan, W. MacNaughtan, I.A. Farhat, and A.G.F. Stapley Polymorphic occurrence and crystallization rates of tristearin/tripalmitin mixtures under non-isothermal conditions Eur. J. Lipid Sci. Technol. 109 2007 49 60
31. G.W.H. Höhne, W.F. Hemminger, and H.-J. Flammersheim Differential Scanning Calorimetry 2nd ed. 2003 Springer-Verlag Berlin, Heidelberg, New York p. 298
32. F.F.A. Hollander, S.X.M. Boerrigter, J. van de Streek, R.F.P. Grimbergen, H. Meekes, and P. Bennema The implication of the connected net topology on the morphology of β-monoacid triacylglycerol crystals J. Phys. Chem. B 103 1999 8301 8309
33. F.F.A. Hollander, D. Kaminski, D. Duret, W.J.P. van Enckevort, H. Meekes, and P. Bennema Growth and morphology of thin fat crystals Food Res. Int. 35 2002 909 918
34. K.L. Humphrey, and S.S. Narine Lipid phase behavior Fat Crystal Networks 2004 Marcel Dekker New York pp. 83-114
35. K.L. Humphrey, and S.S. Narine Diminishing marginal utility of cooling rate increase on the crystallization behavior and physical properties of a lipid sample J. Am. Oil Chem. Soc. 84 2007 709 716
36. T. Inoue, Y. Hisatsugu, M. Suzuki, Z.N. Wang, and L.Q. Zheng Solid-liquid phase behavior of binary fatty acid mixtures 3. Mixtures of oleic acid with capric acid (decanoic acid) and caprylic acid (octanoic acid) Chem. Phys. Lipids 132 2004 225 234
37. T. Inoue, Y. Hisatsugu, R. Yamamoto, and M. Suzuki Solid-liquid phase behavior of binary fatty acid mixtures 1. Oleic acid/stearic acid and oleic acid/behenic acid mixtures Chem. Phys. Lipids 127 2004 143 152
38. T. Inoue, I. Motoda, N. Hiramatsu, M. Suzuki, and K. Sato Phase-behavior of binary mixture of palmitoleic acid (cis-9-hexadecenoic acid) and asclepic acid (cis-11-octadecenoic acid) Chem. Phys. Lipids 66 1993 209 214
39. M. Kellens, W. Meeussen, R. Gehrke, and H. Reynaers Synchrotron radiation investigations of the polymorphic transitions of saturated monoacid triglycerides. 1. Tripalmitin and tristearin Chem. Phys. Lipids 58 1991 131 144
40. M. Knoester, M. Vandente, and P. Debruijn Solid-liquid equilibrium of binary-mixtures of triglycerides with palmitic and stearic chains Chem. Phys. Lipids 9 1972 309 319
41. D.R. Kodali, D. Atkinson, T.G. Redgrave, and D.M. Small Synthesis and polymorphism of 1,2-dipalmitoyl-3-acyl-sn-glycerols J. Am. Oil Chem. Soc. 61 1984 1078 1084
42. D.R. Kodali, D. Atkinson, and D.M. Small Molecular packing in triacyl-sn-glycerols-influences of acyl chain-length and unsaturation J. Disper. Sci. Technol. 10 1989 393 440
43. D.R. Kodali, D. Atkinson, and D.M. Small Molecular packing of 1,2-dipalmitoyl-3-decanoyl-sn-glycerol (PP10)-bilayer, trilayer, and hexalayer structures J. Phys. Chem. 93 1989 4683 4691
44. D.R. Kodali, D. Atkinson, and D.M. Small Polymorphic behavior of 1,2-dipalmitoyl-3-lauroyl (PP12)-and 3-myristoyl (PP14)-sn-glycerols J. Lipid Res. 31 1990 1853 1864
45. T. Koyano, I. Hachiya, and K. Sato Phase behavior of mixed systems of SOS and OSO J. Phys. Chem. 96 1992 10514 10520
46. G.J. Kruger, D.G. Billing, and M. Rademeyer Polymorphism in long-chain N-Alkylammonium halides J.C.A. Boeyens, J.F. Ogilvie, Models, Mysteries and Magic of Molecules 2008 Springer Dordrecht, The Netherlands 219 231
47. K. Larsson Physical properties-structural and physical characteristics F.D. Gunstone, J.L. Harwood, F.B. Padley, The Lipid Handbook 1986 Chapman and Hall London 335 377
48. A.G. Lee Lipid phase-transitions and phase-diagrams. 1. Lipid phase-transitions Biochim. Biophys. Acta-Mol. Cell Res. 472 1977 237 281
49. A.G. Lee Lipid phase-transitions and phase-diagrams. 2. Mixtures involving lipids Biochim. Biophys. Acta-Mol. Cell Res. 472 1977 285 344
50. W. MacNaughtan, I.A. Farhat, C. Himawan, V.M. Starov, and A.G.F. Stapley A differential scanning calorimetry study of the crystallization kinetics of tristearin-tripalmitin mixtures J. Am. Oil Chem. Soc. 83 2006 1 9
51. A.G. Marangoni, and S.S. Narine Identifying key structural indicators of mechanical strength in networks of fat crystals Food Res. Int. 35 2002 957 969
52. A. Minato, S. Ueno, K. Smith, Y. Amemiya, and K. Sato Thermodynamic and kinetic study on phase behavior of binary mixtures of POP and PPO forming molecular compound systems J. Phys. Chem. B 101 1997 3498 3505
53. A. Minato, S. Ueno, J. Yano, K. Smith, H. Seto, Y. Amemiya, and K. Sato Thermal and structural properties of sn-1,3-dipalmitoyl-2-oleoylglycerol and sn-1,3-dioleoyl-2-palmitoylglycerol binary mixtures examined with synchrotron radiation X-ray diffraction J. Am. Oil Chem. Soc. 74 1997 1213 1220
54. W.J. Moore Physical Chemistry 4th ed. 1972 Prentice-Hall Englewood Cliffs, NJ pp. 229-278
55. J.W. Mullin Crystallization 4 ed. 2001 Butterworth-Heinemann Oxford, UK p. 600
56. S.S. Narine, and K.L. Humphrey Extending the capability of pulsed NMR instruments to measure solid fat content as a function of both time and temperature J. Am. Oil Chem. Soc. 81 2004 101 102
57. S.S. Narine, K.L. Humphrey, and L. Bouzidi Modification of the Avrami model for application to the kinetics of the melt crystallization of lipids J. Am. Oil Chem. Soc. 83 2006 913 921
58. Narine, S.S., Humphrey, K.L., Kincs, F.F., 2007. Shortenings and Methods of Making and Using Thereof. Application#: 60/953,609, United States.
59. S.S. Narine, and A.G. Marangoni Fractal nature of fat crystal networks Phys. Rev. E 59 1999 1908 1920
60. S.S. Narine, and A.G. Marangoni Relating structure of fat crystal networks to mechanical properties: a review Food Res. Int. 32 1999 227 248
61. Y. Nibu, and T. Inoue Miscibility of binary phospholipid mixtures under hydrated and non-hydrated conditions. 2. Phosphatidylethanolamines with different acyl-chain lengths Chem. Phys. Lipids 76 1995 159 169
62. R.D. O'Brien Fats and Oils: Formulating and Processing for Applications 2nd ed. 2004 CRC Press Boca Raton, FL p. 529
63. F. Puel, E. Verdurand, P. Taulelle, C. Bebon, D. Colson, J.P. Klein, and S. Veesler Crystallization mechanisms of acicular crystals J. Cryst. Growth 310 2008 110 115
64. J.B. Rossell Phase diagrams of triglyceride systems Adv. Lipid Res. 5 1967 353 408
65. P. Rousset, and M. Rappaz α-Melt-mediated crystallization of 1-palmitoyl-2-oleoyl-3-stearoyl-sn-glycerol J. Am. Oil Chem. Soc. 74 1997 693 697
66. P. Rousset, M. Rappaz, and E. Minner Polymorphism and solidification kinetics of the binary system POS-SOS J. Am. Oil Chem. Soc. 75 1998 857 864
67. K. Sato Polymorphism of pure triacylglycerols and natural fats F.B. Padley, Advances in Applied Lipid Research 1996 JAI Press Inc. London 213 268
68. K. Sato Solidification and phase transformation behaviour of food fats-a review Fett-Lipid 101 1999 467 474
69. K. Sato Crystallization behaviour of fats and lipids-a review Chem. Eng. Sci. 56 2001 2255 2265
70. K. Sato, and N. Garti Crystallization Processes in Fats and Lipid Systems 2001 Marcel Dekker New York p. 533
71. K. Sato, M. Goto, J. Yano, K. Honda, D.R. Kodali, and D.M. Small Atomic resolution structure analysis of β′ polymorph crystal of a triacylglycerol: 1,2-dipalmitoyl-3-myristoyl-sn-glycerol J. Lipid Res. 42 2001 338 345
72. K. Sato, S. Ueno, and J. Yano Molecular interactions and kinetic properties of fats Prog. Lipid Res. 38 1999 91 116
73. A. Sharples Overall Kinetics of Crystallization Introduction to Polymer Crystallization 1966 Edward Arnold London pp. 44-59
74. D.M. Small Glycerides D.J. Hanahan, The Physical Chemistry of Lipids, from Alkanes to Phospholipids 1986 Plenum Press New York 345 372
75. K.W. Smith, F.W. Cain, and G. Talbot Kinetic analysis of non-isothermal differential scanning calorimetry of 1,3-dipalmitoyl-2-oleoylglycerol J. Agric. Food Chem. 53 2005 3031 3040
76. M. Takeuchi, S. Ueno, and K. Sato 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 2002 919 926
77. C.P. Tan, and Y.B.C. Man Differential scanning calorimetric analysis of palm oil, palm oil based products and coconut oil: effects of scanning rate variation Food Chem. 76 2002 89 102
78. B.G. Tenchov Non-uniform lipid distribution in membranes Prog. Surf. Sci. 20 1985 273 340
79. R.E. Timms Phase-behavior of fats and their mixtures Prog. Lipid Res. 23 1984 1 38
80. R.E. Timms Crystallization of fats Chem. Ind. 1991 342 345
81. R.E. Timms The Confectionary Fats Handbook: Properties, Production, and Application. Chapter 2: Physical Chemistry 2003 The Oily Press Bridgewater, England pp. 9-63
82. J.F. Toro-Vazquez, M. Briceno-Montelongo, E. Dibildox-Alvarado, M. Charo-Alonso, and J. Reyes-Hernandez Crystallization kinetics of palm stearin in blends with sesame seed oil J. Am. Oil Chem. Soc. 77 2000 297 310
83. S. Ueno, A. Minato, H. Seto, Y. Amemiya, and K. Sato Synchrotron radiation X-ray diffraction study of liquid crystal formation and polymorphic crystallization of SOS (sn-1,3-distearoyl-2-oleoyl glycerol) J. Phys. Chem. B 101 1997 6847 6854
84. A. van Langevelde, K. van Malssen, E. Sonneveld, R. Peschar, and H. Schenk Crystal packing of a homologous series β′-stable triacylglycerols J. Am. Oil Chem. Soc. 76 1999 603 609
85. J.B. van Mechelen, R. Peschar, and H. Schenk Structures of mono-unsaturated triacylglycerols. I. The β-1 polymorph Acta Crystallogr. Sect. B: Struct. Sci. 62 2006 1121 1130
86. J.B. van Mechelen, R. Peschar, and H. Schenk Structures of mono-unsaturated triacylglycerols. II. The β-2 polymorph Acta Crystallogr. Sect. B: Struct. Sci. 62 2006 1131 1138
87. J.B. van Mechelen, R. Peschar, and H. Schenk Structures of mono-unsaturated triacylglycerols. II. The β-2 polymorph (vol 62, pg 1131, 2006) Acta Crystallogr. Sect. B: Struct. Sci. 63 2007 161 1161
88. T.C. van Soest, S. Dejong, and E.C. Roijers Crystal-structures and melting-points of saturated triacylglycerols in the β-3 phase J. Am. Oil Chem. Soc. 67 1990 415 423
89. P. Walstra, W. Kloek, and T. van Vliet Fat crystal networks N. Garti, K. Sato, Crystallization Processes in Fats and Lipid Systems 2001 Marcel Dekker New York 289 328
90. J. Wei Molecular symmetry, rotational entropy, and elevated melting points Ind. Eng. Chem. Res. 38 1999 5019 5027
91. C.P. Yang, and J.F. Nagle Phase-Transformations in lipids follow classical kinetics with small fractional dimensionalities Phys. Rev. A 37 1988 3993 4000
92. J. Yano, K. Sato, F. Kaneko, D.M. Small, and D.R. Kodali Structural analyses of polymorphic transitions of sn-1,3-distearoyl-2-oleoylglycerol (SOS) and sn-1,3-dioleoyl-2-stearoylglycerol (OSO): assessment on steric hindrance of unsaturated and saturated acyl chain interactions J. Lipid Res. 40 1999 140 151
93. L. Zhang, S. Ueno, S. Miura, and K. Sato 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 2007 219 227