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

Chemistry and Physics of Lipids

Volumn 157, Issue 1, 2009, Pages 21-39

  Boodhoo, Marc V ^a   Bouzidi, Laziz ^a   Narine, Suresh S ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

Binary phase behavior; Crystallization; Isomers; Microstructure; Polymorphism; Rheological properties; Symmetric and asymmetric triacylglycerols

Indexed keywords

1,2 DICAPROYL 3 STEAROYL SN GLYCEROL; 1,3 DICAPROYL 2 STEAROYL SN GLYCEROL; GLYCEROL; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; CRYSTALLIZATION; DIFFERENTIAL SCANNING CALORIMETRY; DNA POLYMORPHISM; FAT CONTENT; MATHEMATICAL MODEL; MICROSCOPY; MISCIBILITY; NUCLEAR MAGNETIC RESONANCE; PHASE TRANSITION; PRIORITY JOURNAL; TEMPERATURE SENSITIVITY; THERMOGRAPHY; X RAY DIFFRACTION;

CALORIMETRY, DIFFERENTIAL SCANNING; COMPLEX MIXTURES; FATTY ACIDS; HARDNESS; MICROSCOPY, POLARIZATION; PHASE TRANSITION; THERMODYNAMICS; TRIGLYCERIDES; X-RAY DIFFRACTION;

EID: 57249089089     PISSN: 00093084     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chemphyslip.2008.08.002     Document Type: Article

References (92)

1. Abes M., Bouzidi L., and Narine S.S. 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. Abes M., Bouzidi L., and Narine S.S. 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. Albon N., Illingworth D., and Hull R. Growth mechanism of trilaurin crystals. J. Cryst. Growth 2 (1968) 26-32
4. Bennema P. Growth and morphology of crystals: integration of theories of roughening and Hartman-Perdok theory. In: Hurle D.T.J. (Ed). Handbook of Crystal Growth (1993), North-Holland Elsevier, Amsterdam 477 (Chapter 7)
5. Bentley P.H., and McCrae W. Efficient synthesis of symmetrical 1,3-diglycerides. J. Org. Chem. 35 (1970) 2082-2083
6. Birker P., Dejong S., Roijers E.C., and Vansoest T.C. Structural investigations of β′ triacylglycerols-an X-ray-diffraction and microscopic study of twinned β′ crystals. J. Am. Oil Chem. Soc. 68 (1991) 895-906
7. Boerrigter S.X.M., Hollander F.F.A., van de Streek J., Bennema P., and Meekes H. Explanation for the needle morphology of crystals applied to a β′ triacylglycerol. Cryst. Growth Des. 2 (2002) 51-54
8. Bouzidi L., Boodhoo M., Humphrey K.L., and Narine S.S. 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. Bragg W.L., and Williams E.J. The effect of thermal agitation on atomic arrangement in alloys. Proc. R. Soc. 145 (1934) 699-730
10. Cebula D.J., McClements D.J., and Povey M.J.W. Small-angle neutron-scattering from voids in crystalline trilaurin. J. Am. Oil Chem. Soc. 67 (1990) 76-78
11. Chapman D. Polymorphism of glycerides. Chem. Rev. 62 (1962) 433-456
12. Chen Y.-P., Tang M., and Kuo J.-C. Solid-liquid equilibria for binary mixtures of N-phenylacetamide with 4-aminoacetophenone, 3-hydroxyacetophenone and 4-hydroxyacetophenone. Fluid Phase Equilibr. 232 (2005) 182-188
13. Costa M.C., Rolemberg M.P., Boros L.A.D., Krahenbuhl M.A., de Oliveira M.G., and Meirelles A.J.A. Solid-liquid equilibrium of binary fatty acid mixtures. J. Chem. Eng. Data 52 (2007) 30-36
14. Cuppen H.M., van Eerd A.R.T., and Meekes H. Needle-like morphology of aspartame. Cryst. Growth Des. 4 (2004) 989-997
15. Cuppen H.M., Beurskens G., Kozuka S., Tsukamoto K., Smits J.M.M., de Gelder R., Grimbergen R.F.P., and Meekes H. Crystal structure and growth behavior of aspartame form I-A. Cryst. Growth Des. 5 (2005) 917-923
16. Dafler J. Polymorphism behavior in fully hydrogenated mono-acid triglycerides. J. Am. Oil Chem. Soc. 54 (1977) 249-254
17. de Jong S.D., and van Soest T.C. Crystal-structures and melting points of saturated triglycerides in β-2 phase. Acta Crystallogr. B-Struct. Commun. 34 (1978) 1570-1583
18. Elisabettini P., Lognay G., Desmedt A., Culot C., Istasse N., Deffense E., and Durant F. Synthesis and physicochemical characterization of mixed diacid triglycerides that contain elaidic acid. J. Am. Oil Chem. Soc. 75 (1998) 285-291
19. Fahey D.A., Small D.M., Kodali D.R., Atkinson D., and Redgrave T.G. Structure and polymorphism of 1,2-dioleoyl-3-acyl-sn-glycerols-3-layered and 6-layered structures. Biochemistry 24 (1985) 3757-3764
20. Foubert I., Dewettink K., van de Walle D., Dijkstra A.J., and Quinn P.J. Physical properties: structural and physical characteristics. In: Gunstone F.D., Harwood J.L., and Dijkstra A.J. (Eds). The Lipid Handbook with CD-ROM (2007), CRC Press, Boca Raton, London, New York 471-534
21. Garidel P., Johann C., and Blume A. The calculation of heat capacity curves and phase diagrams based on regular solution theory. J. Therm. Anal. Calorim. 82 (2005) 447-455
22. Ghotra B.S., Dyal S.D., and Narine S.S. Lipid shortenings: a review. Food Res. Int. 35 (2002) 1015-1048
23. Gibon V., Durant F., and Deroanne C. Study of the polymorphism and intersolubility of some palmitic stearic and oleic triglycerides - PPP, PSP and POP 62 (1985) 656-657
24. Goto M., Kodali D.R., Small D.M., Honda K., Kozawa K., and Uchida T. 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
25. Gray M.S., and Lovegren N.V. Polymorphism of saturated triglycerides. 2. 1,3-dipalmito triglycerides. J. Am. Oil Chem. Soc. 55 (1978) 601-606
26. Gunstone F.D., and Padley F.B. Lipid Technologies and Applications (1997), Marcel Dekker, New York p. 848
27. Hagemann J. Thermal behavior and polymorphism of acylglycerols. In: Garti N., and Sato K. (Eds). Crystallization and Polymorphism of Fats and Fatty Acids (1988), Marcel Dekker, New York 9-98
28. Harrison W.A. Electronic Structure and the Properties of Solids: The Physics of the Chemical Bond (1980), W.H. Freeman and Company, San Francisco 476 pp.
29. Hildebrand J.H. Solubility. XII. Regular solutions. J. Am. Chem. Soc. 51 (1929) 66-80
30. Himawan C., Starov V.M., and Stapley A.G.F. Thermodynamic and kinetic aspects of fat crystallization. Adv. Colloid Interface Sci. 122 (2006) 3-33
31. Himawan C., MacNaughtan W., Farhat I.A., and Stapley A.G.F. Polymorphic occurrence and crystallization rates of tristearin/tripalmitin mixtures under non-isothermal conditions. Eur. J. Lipid Sci. Technol. 109 (2007) 49-60
32. Höhne G.W.H., Hemminger W.F., and Flammersheim H.-J. Differential Scanning Calorimetry. 2nd ed. (2003), Springer-Verlag, Berlin, Heidelberg, New York 298 pp.
33. Hollander F.F.A., Boerrigter S.X.M., van de Streek J., Grimbergen R.F.P., Meekes H., and Bennema P. The implication of the connected net topology on the morphology of β-monoacid triacylglycerol crystals. J. Phys. Chem. B 103 (1999) 8301-8309
34. Hollander F.F.A., Kaminski D., Duret D., van Enckevort W.J.P., Meekes H., and Bennema P. Growth and morphology of thin fat crystals. Food Res. Int. 35 (2002) 909-918
35. Hollander F.F.A., Boerrigter S.X.M., de Streek J.V., Bennema P., Meekes H., Yano J., and Sato K. Comparing the morphology of β-n.n.n with β′-n.n + 2.n and β′-n.n.n-2 triacylglycerol crystals. J. Phys. Chem. B 107 (2003) 5680-5689
36. Humphrey K.L., and Narine S.S. Lipid phase behavior. Fat Crystal Networks (2004), Marcel Dekker, New York pp. 83-114
37. Hvolby A. Expansion of solidifying saturated fats. J. Am. Oil Chem. Soc. 51 (1974) 50-54
38. Inoue T., Hisatsugu Y., Yamamoto R., and Suzuki M. 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
39. Jensen L.H., and Mabis A.J. Refinement of structure of β-tricaprin. Acta Cryst. 21 (1966) 770-781
40. Kellens M., Meeussen W., Gehrke R., and Reynaers H. Synchrotron radiation investigations of the polymorphic transitions of saturated monoacid triglycerides. Part 1. tripalmitin and tristearin. Chem. Phys. Lipids 58 (1991) 131-144
41. Knoester M., Vandente M., and Debruijn P. Solid-liquid equilibrium of binary-mixtures of triglycerides with palmitic and stearic chains. Chem. Phys. Lipids 9 (1972) 309-319
42. Kodali D.R., Atkinson D., Redgrave T.G., and Small D.M. Synthesis and polymorphism of 1,2-dipalmitoyl-3-acyl-sn-glycerols. J. Am. Oil Chem. Soc. 61 (1984) 1078-1084
43. Kodali D.R., Atkinson D., and Small D.M. Molecular packing in triacyl-sn-glycerols-influences of acyl chain-length and unsaturation. J. Disper. Sci. Technol. 10 (1989) 393-440
44. Kodali D.R., Atkinson D., and Small D.M. Molecular packing of 1,2-dipalmitoyl-3-decanoyl-sn-glycerol (PP10)-bilayer, trilayer, and hexalayer structures. J. Phys. Chem. 93 (1989) 4683-4691
45. Kodali D.R., Atkinson D., and Small D.M. Polymorphic behavior of 1,2-dipalmitoyl-3-lauroyl (PP12)- and 3-myristoyl (PP14)-sn-glycerols. J. Lipid Res. 31 (1990) 1853-1864
46. Koynova R., and Caffrey M. An index of lipid phase diagrams. Chem. Phys. Lipids 115 (2002) 107-219
47. Kruger G.J., Billing D.G., and Rademeyer M. Polymorphism in long-chain N-alkylammonium halides. In: Boeyens J.C.A., and Ogilvie J.F. (Eds). Models, Mysteries and Magic of Molecules (2008), Springer, Dordrecht, The Netherlands 219-231
48. Larsson K. Physical properties-structural and physical characteristics. In: Gunstone F.D., Harwood J.L., and Paley F.B. (Eds). The Lipid Handbook (1986), Chapman and Hall, London 335-377
49. Lee A.G. Lipid phase-transitions and phase-diagrams. 1. Lipid phase-transitions. Biochim. Biophys. Acta-Mol. Cell Res. 472 (1977) 237-281
50. Lee A.G. Lipid phase-transitions and phase-diagrams. 2. Mixtures involving lipids. Biochim. Biophys. Acta-Mol. Cell Res. 472 (1977) 285-344
51. List G.R., Mounts T.L., Orthoefer F., and Neff W.E. Margarine and shortening oils by interesterification of liquid and trisaturated triglycerides. J. Am. Oil Chem. Soc. 72 (1995) 379-382
52. Los J.H., van Enckevort W.J.P., Vlieg E., and Floter E. Metastable states in multicomponent liquid-solid systems. I. A kinetic crystallization model. J. Phys. Chem. B 106 (2002) 7321-7330
53. Los J.H., van Enckevort W.J.P., Vlieg E., and Floter E. Metastable states in multicomponent liquid-solid systems. I. A kinetic crystallization model (addition/correction to vol. 106B, pg 7323, 2002). J. Phys. Chem. B 106 (2002) 12651-12651
54. Los J.H., van Enckevort W.J.P., Vlieg E., Floter E., and Gandolfo F.G. Metastable states in multicomponent liquid-solid systems. II. Kinetic phase separation. J. Phys. Chem. B 106 (2002) 7331-7339
55. Lovegren N.V., and Gray M.S. Polymorphism of saturated triglycerides. 1. 1,3-Distearo triglycerides. J. Am. Oil Chem. Soc. 55 (1978) 310-316
56. Lutton E.S. Review of the polymorphism of saturated even glycerides. J. Am. Oil Chem. Soc. 27 (1950) 276-281
57. Lutton E.S. Phase behavior of triglyceride mixtures involving primarily tristearin, 2-oleyldistearin, and triolein. J. Am. Oil Chem. Soc. 32 (1955) 49-53
58. Lutton E.S. Lipid structures. J. Am. Oil Chem. Soc. 49 (1972) 1-9
59. Lutton E.S., Jackson F.L., and Quimby O.T. The polymorphism of the mixed triglycerides of palmitic and stearic acids. J. Am. Chem. Soc. 70 (1948) 2441-2445
60. MacNaughtan W., Farhat I.A., Himawan C., Starov V.M., and Stapley A.G.F. A differential scanning calorimetry study of the crystallization kinetics of tristearin-tripalmitin mixtures. J. Am. Oil Chem. Soc. 83 (2006) 1-9
61. Malkin T., and Meara M.L. An X-ray and thermal examination of the glycerides. Part IV. Symmetrical mixed triglycerides, CH(O COR′)(CH2 O COR)(2). J. Chem. Soc. (1939) 103-108
62. Malkin T., and Meara M.L. An X-ray and thermal examination of the glycerides. Part VI. Symmetrical mixed triglycerides, CH(O COR′)(CH2 OCOR)(2) (continued). J. Chem. Soc. (1939) 1141-1144
63. Marangoni A.G., and Narine S.S. Identifying key structural indicators of mechanical strength in networks of fat crystals. Food Res. Int. 35 (2002) 957-969
64. Narine S.S., and Humphrey K.L. 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
65. Narine S.S., and Marangoni A.G. Relating structure of fat crystal networks to mechanical properties: a review. Food Res. Int. 32 (1999) 227-248
66. Nibu Y., and Inoue T. 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
67. Precht D., and Frede E. Triclinic lattice-constants of saturated mono-acid triglycerides. Acta Crystallogr. B-Struct. Commun. 39 (1983) 381-388
68. Puel F., Verdurand E., Taulelle P., Bebon C., Colson D., Klein J.P., and Veesler S. Crystallization mechanisms of acicular crystals. J. Cryst. Growth 310 (2008) 110-115
69. Rossell J.B. Phase diagrams of triglyceride systems. Adv. Lipid Res. 5 (1967) 353-408
70. Rousset P., and Rappaz M. α-Melt-mediated crystallization of 1-palmitoyl-2-oleoyl-3-stearoyl-sn-glycerol. J. Am. Oil Chem. Soc. 74 (1997) 693-697
71. Rousset P., Rappaz M., and Minner E. Polymorphism and solidification kinetics of the binary system POS-SOS. J. Am. Oil Chem. Soc. 75 (1998) 857-864
72. Sato K. Polymorphism of pure triacylglycerols and natural fats. In: Padley F.B. (Ed). Advances in Applied Lipid Research (1996), JAI Press Inc., London 213-268
73. Sato K. Solidification and phase transformation behaviour of food fats-a review. Fett-Lipid 101 (1999) 467-474
74. Sato K. Crystallization behaviour of fats and lipids-a review. Chem. Eng. Sci. 56 (2001) 2255-2265
75. Sato K., and Ueno S. Polymorphism of fats and oils. In: Shahidi F. (Ed). Edible Oils and Fat Products: Chemistry, Properties, and Health Effects (2005), John Wiley & Sons, Inc., Hoboken, NJ 77-120
76. Sato K., Ueno S., and Yano J. Molecular interactions and kinetic properties of fats. Prog. Lipid Res. 38 (1999) 91-116
77. Sato K., Goto M., Yano J., Honda K., Kodali D.R., and Small D.M. 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
78. Skoda W., and van den Tempel M. Growth kinetics of triglyceride crystals. J. Cryst. Growth 1 (1967) 207-217
79. Small D.M. Glycerides. In: Hanahan D.J. (Ed). The Physical Chemistry of Lipids, from Alkanes to Phospholipids (1986), Plenum Press, New York 345-372
80. Tenchov B.G. Non-uniform lipid distribution in membranes. Prog. Surf. Sci. 20 (1985) 273-340
81. Timms R.E. Phase-behavior of fats and their mixtures. Prog. Lipid Res. 23 (1984) 1-38
82. Timms R.E. Chapter 2: Physical Chemistry. The Confectionary Fats Handbook: Properties, Production and Application (2003), The Oily Press, Bridgewater, England pp. 9-63
83. Ueno S., Minato A., Seto H., Amemiya Y., and Sato K. 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. van der Eerden J.P. Crystal growth mechanisms. In: Hurdle D. (Ed). Handbook of Crystal Growth (1993), Elsevier, North Holland, Amsterdam 307-475
85. van Langevelde A., van Malssen K., Sonneveld E., Peschar R., and Schenk H. Crystal packing of a homologous series β′-stable triacylglycerols. J. Am. Oil Chem. Soc. 76 (1999) 603-609
86. van Langevelde A., Peschar R., and Schenk H. Structure of b-trimyristin and b-tristearin from high-resolution X-ray powder diffraction data. Acta Crystallogr. Sect. B-Struct. Sci. 57 (2001) 372-377
87. van Mechelen J.B., Peschar R., and Schenk H. Structures of mono-unsaturated triacylglycerols. III. The β-2 polymorphs of trans-mono-unsaturated triacylglycerols and related fully saturated triacylglycerols. Acta Crystallogr. B-Struct. Sci. 64 (2008) 240-248
88. van Mechelen J.B., Peschar R., and Schenk H. Structures of mono-unsaturated triacylglycerols. IV. The highest melting β′-2 polymorphs of trans-mono-unsaturated triacylglycerols and related saturated TAGs and their polymorphic stability. Acta Crystallogr. B-Struct. Sci. 64 (2008) 249-259
89. van Soest T.C., Dejong S., and Roijers E.C. Crystal-structures and melting-points of saturated triacylglycerols in the β-3 phase. J. Am. Oil Chem. Soc. 67 (1990) 415-423
90. Walstra P., Kloek W., and van Vliet T. Fat crystal networks. In: Garti N., and Sato K. (Eds). Crystallization Processes in Fats and Lipid Systems (2001), Marcel Dekker, New York 289-328
91. Yano J., Sato K., Kaneko F., Small D.M., and Kodali D.R. 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
92. Zhang L., Ueno S., Miura S., and Sato K. 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