Table of Contents
ISRN Chemical Engineering
Volume 2013 (2013), Article ID 124767, 21 pages
http://dx.doi.org/10.1155/2013/124767
Review Article

The Food Additive Polyglycerol Polyricinoleate (E-476): Structure, Applications, and Production Methods

Department of Chemical Engineering, University of Murcia, Campus de Espinardo, 30100 Murcia, Spain

Received 27 September 2012; Accepted 4 December 2012

Academic Editors: M. Assael, Z. Fang, A. Gil, F. Lefebvre, J. Subrt, and J. E. Ten Elshof

Copyright © 2013 Josefa Bastida-Rodríguez. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. R. MacRae, R. K. Robinson, and M. J. Sadler, Eds., Encyclopaedia of Food Science, Food Technology, and Nutrition, vol. 8, Academic Press, New York, NY, USA, 1993.
  2. Y. H. Hui, Ed., Encyclopedia of Food Science and Technology, vol. 4, John Wiley & Sons, New York, NY, USA, 1992.
  3. P. J. Fellows, Food Processing Technology: Principles and Practices, Woodhead Publishing Limited, Cambridge, UK, 3rd edition, 2009.
  4. A. L. Branen, P. M. Davidson, S. Salminen, and J. Thorngate, Eds., Food Additives, Taylor & Francis, Boca Raton, Fla, USA, 2001.
  5. T. E. Furia, Ed., Handbook of Food Additives, vol. 2, CRC Press, New York, NY, USA, 2nd edition, 1980.
  6. J. A. Maga and A. T. Tu, Eds., Food Additive Toxicology, Taylor & Francis, London, UK, 1995.
  7. J. S. Smith, Ed., Food Additive User's Handbook, Springer, New York, NY, USA, 1991.
  8. Codex alimentarius, 2012, http://www.codexalimentarius.org.
  9. H. Moonen and H. Bas ", “Mono- and diglycerides,” in Emulsifiers in Food Technology, R. J. Whitehurst, Ed., John Wiley & Sons, New York, NY, USA, 2008. View at Google Scholar
  10. NPCS Board of Consultants & Engineers, The Complete Book on Emulsifiers With Uses, Formulae and Processes, 2007.
  11. G. L. Hasenhuettl and R. W. Hartel, Eds., Emulsifiers and Their Applications, Springer, New York, NY, USA, 2008.
  12. C. Stauffer, Emulsifiers, Eagan Press, 1999.
  13. N. Garti, “Food emulsifiers. structure-reactivity relationships, design, and applications,” in Physical Properties of Lipids, A. G. Marangoni and S. S. Narine, Eds., Taylor & Francis, London, UK, 2002. View at Google Scholar
  14. C. C. Cai, “Emulsifiers used in food applications, focusing on the meat processing industry,” Palsgaard Technical Paper, 2011. View at Google Scholar
  15. C. E. Stauffer, “Emulsifiers for the food industry,” in Bailey’a Induatrial Oil and Fat Producta, F. Shahidi, Ed., John Wiley & Sons, New York, NY, USA, 2005. View at Google Scholar
  16. M. Gómez, S. Del Real, C. M. Rosell, F. Ronda, C. A. Blanco, and P. A. Caballero, “Functionality of different emulsifiers on the performance of breadmaking and wheat bread quality,” European Food Research and Technology, vol. 219, no. 2, pp. 145–150, 2004. View at Publisher · View at Google Scholar · View at Scopus
  17. L. Stampfli and B. Nersten, “Emulsifiers in bread making,” Food Chemistry, vol. 52, pp. 353–360, 1995. View at Google Scholar
  18. Z. Kohajdová, J. Karovičová, and Š. Schmidt , “Significance of emulsifiers and hydrocolloids in bakery industry,” Acta Chimica Slovaca, vol. 2, pp. 46–461, 2009. View at Google Scholar
  19. R. T. McIntyre, “Polyglycerol esters,” Journal of the American Oil Chemists' Society, vol. 56, pp. A835–A840, 1979. View at Google Scholar
  20. M. F. Stewart and E. J. Hughes, “Polyglycerol esters as food additives,” Process Biochemistry Journal, vol. 7, pp. 27–28, 1972. View at Google Scholar
  21. N. Garti, G. F. Remon, and B. Zaidman, “Polyglycerol esters of vegetable oils,” Tenside, Surfactants, Detergents, vol. 23, no. 6, pp. 320–324, 1986. View at Google Scholar · View at Scopus
  22. N. Garti, A. Aserin, and B. Zaidman, “Polyglycerol esters: optimization and techno-economic evaluation,” Journal of the American Oil Chemists' Society, vol. 58, no. 9, pp. 878–883, 1981. View at Publisher · View at Google Scholar · View at Scopus
  23. “Polyglycerols in food applications,” Application data sheet. Solvay Chemicals International.
  24. J. Holstborg, B. V. Pedersen, N. Krog, and S. K. Olesen, “Physical properties of diglycerol esters in relation to rheology and stability of protein-stabilised emulsions,” Colloids and Surfaces B, vol. 12, no. 3–6, pp. 383–390, 1999. View at Publisher · View at Google Scholar · View at Scopus
  25. S. K. Olesen and N. Krog, “Phase behaviour of new food emulsifiers and their application,” in Oils and Fats in Food Applications: Proceedings of the Food Applications Session of the 22nd Congress of the International Society of Fats Research (ISF), Kuala Lumpur, Malaysia, 7–12 September 1997, K. G. Berger, Ed., 1997. View at Google Scholar
  26. A. Sein, J. A. Verheij, and W. G. M. Agterof, “Rheological characterization, crystallization, and gelation behavior of monoglyceride gels,” Journal of Colloid and Interface Science, vol. 249, no. 2, pp. 412–422, 2002. View at Publisher · View at Google Scholar · View at Scopus
  27. N. Krog, “Crystallization properties and lyotropic phase behavior of food emulsifiers,” in Crystallization Processes in Fats and Lipid Systems, N. Garti and K. Sato, Eds., Taylor & Francis, London, UK, 2001. View at Google Scholar
  28. P. Seiden and J. B. Martin, “Process for preparing polyglycerol,” US 3,968,169, 1976.
  29. “Polyglycerols—general overview,” Product data sheet. Solvay Chemical International.
  30. V. Norn, “Polyglycerol esters,” in Emulsifiers in Food Technology, R. J. Whitehurst, Ed., 2008. View at Google Scholar
  31. T. Ushikusa, T. Maruyama, I. Nhya, and M. Okada, “Pyrolysis behaviors and thermostability of polyglycerols and polyglycerol fatty acid esters,” Journal of the Japan Oil Chemists' Society, vol. 39, no. 5, pp. 314–320, 1990. View at Google Scholar
  32. “Polyglycerols for ester production,” Application data sheet. Solvay Chemical International.
  33. F. van de Velde, F. Weinbreck, M. W. Edelman, E. Van Der Linden, and R. H. Tromp, “Visualisation of biopolymer mixtures using confocal scanning laser microscopy (CSLM) and covalent labelling techniques,” Colloids and Surfaces B, vol. 31, no. 1–4, pp. 159–168, 2003. View at Publisher · View at Google Scholar · View at Scopus
  34. I. Kobayashi, X. Lou, S. Mukataka, and M. Nakajima, “Preparation of monodisperse water-in-oil-in-water emulsions using microfluidization and straight-through microchannel emulsification,” Journal of the American Oil Chemists' Society, vol. 82, no. 1, pp. 65–71, 2005. View at Google Scholar · View at Scopus
  35. J. Su, J. Flanagan, Y. Hemar, and H. Singh, “Synergistic effects of polyglycerol ester of polyricinoleic acid and sodium caseinate on the stabilisation of water-oil-water emulsions,” Food Hydrocolloids, vol. 20, no. 2-3, pp. 261–268, 2006. View at Publisher · View at Google Scholar · View at Scopus
  36. J. Surh, G. T. Vladisavljević, S. Mun, and D. J. McClements, “Preparation and characterization of water/oil and water/oil/water emulsions containing biopolymer-gelled water droplets,” Journal of Agricultural and Food Chemistry, vol. 55, no. 1, pp. 175–184, 2007. View at Publisher · View at Google Scholar · View at Scopus
  37. A. Benichou, A. Aserin, and N. Garti, “Polyols, high pressure, and refractive indices equalization for improved stability of W/O emulsions for food applications,” Journal of Dispersion Science and Technology, vol. 22, no. 2-3, pp. 269–280, 2001. View at Publisher · View at Google Scholar · View at Scopus
  38. S. Mun, Y. Choi, S. J. Rho, C. G. Kang, C. H. Park, and Y. R. Kim, “Preparation and characterization of water/oil/water emulsions stabilized by polyglycerol polyricinoleate and whey protein isolate,” Journal of Food Science, vol. 75, no. 2, pp. E116–E125, 2010. View at Publisher · View at Google Scholar · View at Scopus
  39. D. Saǧlam, P. Venema, R. de Vries, L. M. C. Sagis, and E. van der Linden, “Preparation of high protein micro-particles using two-step emulsification,” Food Hydrocolloids, vol. 25, no. 5, pp. 1139–1148, 2011. View at Publisher · View at Google Scholar · View at Scopus
  40. R. Wilson, B. J. van Schie, and D. Howes, “Overview of the preparation, use and biological studies on polyglycerol polyricinoleate (PGPR),” Food and Chemical Toxicology, vol. 36, no. 9-10, pp. 711–718, 1998. View at Publisher · View at Google Scholar · View at Scopus
  41. E. Flack, “Margarines and spreads,” in Food Emulsifiers and Their Applications, G. L. Hasenhuettl and R. W. Hartel, Eds., Springer, New York, NY, USA, 1997. View at Google Scholar
  42. S. M. Clegg, A. K. Moore, and S. A. Jones, “Low-fat margarine spreads as affected by aqueous phase hydrocolloids,” Journal of Food Science, vol. 61, no. 5, pp. 1073–1079, 1996. View at Google Scholar · View at Scopus
  43. B. Schantz and H. Rohm, “Influence of lecithin-PGPR blends on the rheological properties of chocolate,” Lebensm-wiss u-Technol, vol. 38, no. 1, pp. 41–45, 2005. View at Publisher · View at Google Scholar · View at Scopus
  44. H. F. Banford, K. J. Gardiner, G. R. Howat, and A. F. Thomson, “The use of polyglycerol polyricinoleate in chocolate,” Confectionery Production, vol. 36, pp. 359–365, 1970. View at Google Scholar
  45. P. Lonchampt and R. W. Hartel, “Fat bloom in chocolate and compound coatings,” European Journal of Lipid Science and Technology, vol. 106, pp. 241–274, 2004. View at Google Scholar
  46. R. Peschar, M. M. Pop, D. J. A. de Ridder, J. B. van Mechelen, R. A. J. Driessen, and H. Schenk, “Crystal structures of 1,3-distearoyl-2-oleoylglycerol and cocoa butter in the β(V) phase reveal the driving force behind the occurrence of fat bloom on chocolate,” Journal of Physical Chemistry B, vol. 108, no. 40, pp. 15450–15453, 2004. View at Publisher · View at Google Scholar · View at Scopus
  47. H. Schenk and R. Peschar, “Understanding the structure of chocolate,” Radiation Physics and Chemistry, vol. 71, pp. 829–835, 2004. View at Google Scholar
  48. R. Wilson and M. Smith, “A three-generation reproduction study on polyglycerol polyricinoleate (PGPR) in wistar rats,” Food and Chemical Toxicology, vol. 36, no. 9-10, pp. 739–741, 1998. View at Publisher · View at Google Scholar · View at Scopus
  49. R. Wilson and M. Smith, “Human studies on polyglycerol polyricinoleate (PGPR),” Food and Chemical Toxicology, vol. 36, no. 9-10, pp. 743–745, 1998. View at Publisher · View at Google Scholar · View at Scopus
  50. R. Wilson, B. H. Doell, W. Groger, J. Hope, and J. B. M. Gellatly, “The physiology of liver enlargement,” in Metabolic Aspects of Food Safety, F. J. C. Roe, Ed., 1970. View at Google Scholar
  51. D. Howes, R. Wilson, and C. T. James, “The fate of ingested glyceran esters of condensed castor oil fatty acids [polyglycerol polyricinoleate (PGPR)] in the rat,” Food and Chemical Toxicology, vol. 36, no. 9-10, pp. 719–738, 1998. View at Publisher · View at Google Scholar · View at Scopus
  52. J. Philp McL, “Evaluation of the safety of foods,” Proceedings of the Nutrition Society, vol. 40, pp. 47–56, 1981. View at Google Scholar
  53. JECFA, “17th Report on the Joint FAO/WHO Expert Committee on Food Additives,” 1973, http://www.fao.org/.
  54. “Report from the Commission on Dietary Food Additive Intake in the European Union,” Commission of the European Communities, Brussels, Belgium, 2001.
  55. Directive No 95/2/EC of the European Parliament and of the Council of 20 February 1995 on food additives other than colours and sweeteners.
  56. Commission Directive 2008/84/EC of the European Parliament and of the Council of 27 August 2008 laying down specific purity criteria on food additives other than colours and sweeteners.
  57. P. Denecke, G. Börner, and V. V. Allmen, “Method of preparing polyglycerol polyricinoleic fatty acid esters,” GB2073232A, 1981.
  58. S. N. Modak and J. G. Kane, “Studies in estolides. I. Kinetics of estolide formation and decomposition,” Journal of the American Oil Chemists' Society, vol. 42, pp. 428–232, 1965. View at Google Scholar
  59. K. T. Achaya, “Chemical derivatives of castor oil,” Journal of the American Oil Chemists' Society, vol. 48, no. 11, pp. 758–763, 1971. View at Google Scholar · View at Scopus
  60. R. Tenore, “Process for the direct manufacture of polyglycerol polyricinoleate,” WO 2007/027447 A1, 2007. View at Google Scholar
  61. A. Manresa, A. Bódalo, J. L. Gómez et al., “Method for obtaining polyglycerol polyricinoleate,” WO 2088/031908 A1, 2008. View at Google Scholar
  62. A. Bódalo, J. Bastida, M. F. Máximo, M. C. Montiel, and M. D. Murcia, “Enzymatic biosynthesis of ricinoleic acid estolides,” Biochemical Engineering Journal, vol. 26, pp. 155–158, 2005. View at Google Scholar
  63. A. Bódalo, J. Bastida, M. F. Máximo, M. C. Montiel, M. Gómez, and M. D. Murcia, “Production of ricinoleic acid estolide with free and immobilised lipase from Candida rugosa,” Biochemical Engineering Journal, vol. 39, pp. 450–456, 2008. View at Google Scholar
  64. A. Bódalo, J. Bastida, M. F. Máximo, M. C. Montiel, M. D. Murcia, and S. Ortega, “Influence of the operating conditions on lipase-catalysed synthesis of ricinoleic acid estolides in solvent-free systems,” Biochemical Engineering Journal, vol. 44, no. 2-3, pp. 214–219, 2009. View at Publisher · View at Google Scholar · View at Scopus
  65. A. Bódalo, J. Bastida, M. F. Máximo, M. C. Montiel, M. Gómez, and S. Ortega, “Screening and selection of lipases for the enzymatic production of polyglycerol polyricinoleate,” Biochemical Engineering Journal, vol. 46, pp. 217–222, 2009. View at Google Scholar
  66. J. L. Gómez, J. Bastida, M. F. Máximo, M. C. Montiel, M. D. Murcia, and S. Ortega, “Solvent-free polyglycerol polyricinoleate synthesis mediated by lipase from Rhizopus arrhizus,” Biochemical Engineering Journal, vol. 54, pp. 111–116, 2011. View at Google Scholar
  67. N. N. Gandhi, “Applications of lipase,” Journal of the American Oil Chemists' Society, vol. 74, pp. 621–634, 1997. View at Google Scholar
  68. D. G. Hayes and R. Kleiman, “Lipase-catalyzed synthesis and properties of estolides and their esters,” Journal of the American Oil Chemists' Society, vol. 72, no. 11, pp. 1309–1316, 1995. View at Publisher · View at Google Scholar · View at Scopus
  69. D. G. Hayes, “The catalytic activity of lipases toward hydroxyl fatty acids. A review,” Journal of the American Oil Chemists' Society, vol. 73, pp. 543–549, 1996. View at Google Scholar
  70. F. Ergan, M. Trani, and G. André, “Production of glycerides from glycerol and fatty acid by immobilized lipases in non-aqueous media,” Biotechnology and Bioengineering, vol. 35, no. 2, pp. 195–200, 1990. View at Google Scholar · View at Scopus
  71. D. Charlemagne and M. D. Legoy, “Enzymatic synthesis of polyglycerol-fatty acid esters in solvent-free system,” Journal of the American Oil Chemists' Society, vol. 72, pp. 61–65, 1995. View at Google Scholar
  72. G. W. V. Cave, C. L. Raston, and J. L. Scott, “Recent advances in solventless organic reactions: towards benign synthesis with remarkable versatility,” Chemical Communications, no. 21, pp. 2159–2169, 2001. View at Google Scholar · View at Scopus
  73. G. Hills, “Industrial use of lipases to product fatty acid esters,” European Journal of Lipid Science and Technology, vol. 105, pp. 601–607, 2003. View at Google Scholar
  74. P. T. Anastas and J. C. Warner, Green Chemistry: Theory and Practice, Oxford University Press, New York, NY, USA, 1998.
  75. C. Yamaguchi, M. Akita, S. Asaoka, and F. Osada, “Enzymatic manufacture of castor oil fatty acid estolides,” JP 8916591, 1988. View at Google Scholar
  76. C. Yamaguchi, A. Tooyama, S. Asaoka, and F. Osada, “Manufacture of glycerin-free estolides from castor oil with lipase,” JP 9013387, 1989. View at Google Scholar
  77. C. Yamaguchi et al., “Production of estolide,” JP 5211878, 1993. View at Google Scholar
  78. Y. Yoshida et al., “Production of estolide from ricinoleic acid,” JP 5304966, 1993. View at Google Scholar
  79. Y. Yoshida, M. Kawase, C. Yamaguchi, and T. Yamane, “Enzymatic synthesis of estolides by a bioreactor,” Journal of the American Oil Chemists' Society, vol. 74, no. 3, pp. 261–267, 1997. View at Google Scholar · View at Scopus
  80. Y. Yoshida, M. Kawase, C. Yamaguchi, and T. Yamane, “Synthesis of estolides with immobilized lipase,” Yukagaku, vol. 44, pp. 328–333, 1995. View at Google Scholar
  81. A. Bódalo, E. Gómez, J. L. Gómez, J. Bastida, M. F. Máximo, and F. Díaz, “A comparison of different methods of β-galactosidase immobilization,” Process Biochemistry Journal, vol. 26, pp. 349–353, 1991. View at Google Scholar
  82. J. L. Gómez, A. Bódalo, E. Gómez, J. Bastida, A. M. Hidalgo, and M. Gómez, “Immobilisation of peroxidase on glass beads: an improved alternative for phenol removal,” Enzyme and Microbial Technology, vol. 39, pp. 2016–2022, 2006. View at Google Scholar
  83. E. F. Hartree, “Protein determination and improved modification of the Lowry’s method which gives a linear photometric response,” Analytical Biochemistry, vol. 42, pp. 422–427, 1973. View at Google Scholar
  84. ASTM D974-06, “Standard test method for acid and base number by color indicator titration”.
  85. J. C. Santos, G. F. M. Nunes, A. B. R. Moreira, V. H. Perez, and H. F. de Castro, “Characterization of Candida rugosa lipase immobilized on poly(N-methylolacrylamide) and its application in butyl butyrate synthesis,” Chemical Engineering and Technology, vol. 30, no. 9, pp. 1255–1261, 2007. View at Publisher · View at Google Scholar · View at Scopus
  86. L. Guo, Z. Zhang, Y. Zhu, J. Li, and Z. Xie, “Synthesis of polysiloxane-polyester copolymer by lipase-catalyzed polycondensation,” Journal of Applied Polymer Science, vol. 108, no. 3, pp. 1901–1907, 2008. View at Publisher · View at Google Scholar · View at Scopus
  87. H. T. Dang, O. Obiri, and D. G. Hayes, “Feed batch addition of saccharide during saccharide-fatty acid esterification catalyzed by immobilized lipase: time course, water activity, and kinetic model,” Journal of the American Oil Chemists' Society, vol. 82, no. 7, pp. 487–493, 2005. View at Publisher · View at Google Scholar · View at Scopus
  88. M. Goldberg, D. Thomas, and M. D. Legoy, “The control of lipase-catalysed transesterification and esterification reaction rates. Effects of substrate polarity, water activity and water molecules on enzyme activity,” European Journal of Biochemistry, vol. 190, no. 3, pp. 603–609, 1990. View at Google Scholar · View at Scopus
  89. A. R. M. Yahya, W. A. Anderson, and M. Moo-Young, “Ester synthesis in lipase catalysed reactions,” Enzyme and Microbial Technology, vol. 23, pp. 438–450, 1998. View at Google Scholar
  90. A. M. Klibanov, “Enzymatic catalysis in anhydrous organic solvents,” Trends in Biochemical Sciences, vol. 14, no. 4, pp. 141–144, 1989. View at Google Scholar · View at Scopus
  91. “Sigma Aldrich catalog,” En, http://www.sigmaaldrich.com/.
  92. Y. Yesiloglu, “Utilization of bentonite as a support material for immobilisation of Candida rugosa lipase,” Process Biochemistry Journal, vol. 40, pp. 2155–2159, 2005. View at Google Scholar
  93. Committee on Food Chemicals Codex, Food and Nutrition Board, and Institute of Medicine, Food Chemicals Codex, 5th edition, 2004.
  94. S. Ortega Requena, Síntesis biocatalítica de polirricinoleato de poliglicerol [Ph.D. thesis], University of Murcia, Murcia, Spain, 2012.