Solubility and Stability of β-Cyclodextrin–Terpineol Inclusion Complex as Affected by Water
Tóm tắt
In the present work, inclusion complexes of α-terpineol (Terp) and β-cyclodextrin (BCD) were prepared by the coprecipitation method. Phase solubility studies were performed and thermodynamic parameters involved in the complex formation were calculated. The solubility of Terp increased linearly as the concentration of BCD was increased, confirming the 1:1 stoichiometry of the complex. The stability constants decreased along with increasing temperature. The negative value of the enthalpy and of the Gibbs free energy demonstrated that the process is exothermic and spontaneous. Since complexation gives more ordered systems, the negative value obtained for the entropy change evidenced the encapsulation of Terp. Terp was completely encapsulated in BCD at the preparation conditions and studied molar ratios, as confirmed in the freeze-dried samples by differential scanning calorimeter. The presence of Terp greatly modified the BCD water sorption curves, and the amount of adsorbed water was lower for the complexes. The limited water solubility of Terp could be overcome by the formation of BCD inclusion complexes, and the complexes were stable at different storage conditions (relative humidities 11–97% and 25 °C). The obtained phase solubility data are useful for food or pharmaceutical products formulation involving cyclodextrins and stability predictions.
Tài liệu tham khảo
M.E. Brewster, T. Loftsson, Adv. Drug Deliv. Rev. 59, 645–666 (2007)
A. Hedges, Am Chem Soc 98, 2035–2044 (1998)
M.L. Calabrò, S. Tommasini, P. Donato, D. Raneri, R. Stancanelli, P. Ficarra, J. Pharm. Biomed. Anal. 35, 365–377 (2004)
C. Alvariza, R. Usero, F. Mendicuti, Spectrochim Acta A 67, 420–429 (2007)
C. Lucas-Abellán, I. Fortea, J.M. López-Nicolás, E. Núñez-Delicado, Food Chem. 104, 39–44 (2007)
N.E. Polyakov, T. Leshina, T.A. Konovalova, E.O. Hand, L.D. Kispert, Free Radic. Biol. Med. 36, 872–880 (2004)
L. Szente, J. Szejtli, Trends Food Sci. Technol. 15, 137–142 (2004)
V.T. Karathanos, I. Mourtzinos, K. Yannakopoulou, N.K. Andrikopoulos, Food Chem. 101, 652–658 (2007)
Z. Lu, B. Cheng, Y. Hu, Y. Zhang, G. Zou, Food Chem. 113, 17–20 (2009)
A. Adams, J.C.R. Demyttenaere, N. De Kimpe, Food Chem. 80, 525–534 (2003)
S.P. Bhatia, D. McGinty, C.S. Letizia, A.M. Api, Food Chem. Toxicol. 46, 128–130 (2008)
D. Pitarokili, M. Couladis, N. Petsikos-Panayotarou, O. Tzakou, J. Agric. Food Chem. 50, 6688 (2002)
R. Tisserand, T. Balacs, Essential Oil Safety: A Guide for Health Care Professionals (New York, Churchill Livingstone, 1995)
S.B. Hassan, H. Gali-Muhtasib, H. Göransson, R. Larsson, Anticancer Res. 30, 1911–1919 (2010)
M. Arias, M.S. García-Falcón, L. García-Río, J.C. Mejuto, R. Rial-Otero, J. Simal-Gándara, J. Food Eng. 78(1), 69–73 (2007)
I. Fichan, C. Larroche, J.B. Gros, J. Chem. Eng. Data 44(56–62), 109–114 (1999)
B. Bhandari, B. D’Arcy, G. Young, Int. J. Food Sci. Technol. 36, 453–461 (2001)
T. Higuchi, K. Connors, Adv Anal Chem Instrum 4, 117–212 (1965)
T. Loftsson, M.E. Brewster, J. Pharm. Sci. 85, 1017–1025 (1996)
S. Tommasini, D. Raneri, R. Ficarra, M.L. Calabrò, R. Stancanelli, P. Ficarra, J. Pharm. Biomed. Anal. 35, 379–387 (2004)
M.J. Choi, A. Soottitantawat, O. Nuchuchua, S.G. Min, U. Ruktanonchai, Food Res. Int. 42, 148–156 (2009)
M. Regiert, J Incl Phenomenon Macrocycl Chem 57, 471–474 (2007)
L. Greenspan, J. Res. Natl Bur. Stand. 81A, 89–96 (1977)
M.J. O’Neil (ed.), Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals, 12th edn. (Merck, Whitehouse Station, 2006). 9103
M.V. Rekharsky, Y. Inoue, Chem. Rev. 98, 1875–1917 (1998)
T. Hoshino, K. Uekama, J. Pitha, Int. J. Pharm. 98, 239–242 (1993)
I. Mourtzinos, N. Kalogeropoulos, S.E. Papadakis, K. Konstantinou, V.T. Karathanos, J. Food Sci. 73(1), 89–94 (2008)
A. Cooper, D.D. MacNicol, J Chem Soc Perkin Trans 2, 761–763 (1978)
R.O. Williams, V. Mahaguna, M. Sriwongjanya, Eur. J. Pharm. Biopharm. 46, 355–360 (1998)
T. Pralhad, K. Rajendrakumar, J. Pharm. Biomed. Anal. 34, 333–339 (2004)
C. dos Santos, M.F. Mazzobre, B. Elizalde, M.P. Buera, Alimentos Cienc. Ingeniería Alimentos 16(2), 71–73 (2007)
G. Astray, C. Gonzalez-Barreiro, J.C. Mejuto, R. Rial-Otero, J. Simal-Gándara, Food Hydrocolloids 23, 1631–1640 (2009)
M.F. Mazzobre, B. Elizalde, C. dos Santos, P. Ponce Cevallos, M.P. Buera, Nanoencapsulation of Food Ingredients in Cyclodextrins: Effect of Water Interactions and Ligand Structure, in Functional Food Product Development. Part I: New Technologies For Functional Food Manufacture, ed. by J. Smith, E. Charter (Wiley, Blackwell, 2010), pp. 25–38
P.A. Ponce Cevallos, M.P. Buera, B.E. Elizalde, J. Food Eng. 99, 70–75 (2010)
G. Astray, J.C. Mejuto, J. Morales, R. Rial-Otero, J. Simal-Gándara, Food Res. Int. 43, 1212–1218 (2010)