Solubilities of Biologically Active Phenolic Compounds: Measurements and Modeling

被引:90
作者
Queimada, Antonio J. [1 ]
Mota, Fatima L. [1 ]
Pinho, Simao P. [2 ]
Macedo, Eugenia A. [1 ]
机构
[1] Univ Porto, Fac Engn, Dept Engn Quim, LSRE, P-4200465 Oporto, Portugal
[2] Inst Politecn Braganca, LSRE, P-5301857 Braganca, Portugal
关键词
EQUATION-OF-STATE; UNIFAC GROUP-CONTRIBUTION; LIQUID-EQUILIBRIA; HEAT-CAPACITY; GALLIC ACID; WATER; ANTIOXIDANT; TEMPERATURE; PREDICTION; ETHANOL;
D O I
10.1021/jp808683y
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Aqueous solubilities of natural phenolic compounds from different families (hydroxyphenyl, polyphenol, hydroxybenzoic, and phenylpropenoic) were experimentally obtained. Measurements were performed on tyrosol and ellagic, protocatechuic, syringic, and o-coumaric acids, at five different temperatures (from 288.2 to 323.2 K), using the standard shake-flask method, followed by compositional analysis using UV spectrophotometry. To verify the accuracy of the spectrophotometric method, some data points were measured by gravimetry, and in general, the values obtained with the two methods are in good agreement (deviations lower than 11%). To adequately understand the solubilization process, melting properties of the pure phenolics were obtained by differential scanning calorimetry (DSC), and apparent acid dissociation constants were measured by potentiometry titration. The aqueous solubilities followed the expected general exponential trend. The melting temperatures did not follow the same solubility tendency, and for tyrosol and ellagic acid, not only the size and extent of hydrogen bonding, but also the energy associated with their crystal structures, determine the solubility. For these binary systems, acid dissociation is not important. Approaches for modeling the measured data were evaluated. These included an excess Gibbs energy equation, the modified UNIQUAC model, and the cubic-plus-association (CPA) equation of state. Particularly for the CPA approach, a new methodology that explicitly takes into account the number and nature of the associating sites and the prediction of the pure-component parameters from molecular structure is proposed. The results indicate that these are appropriate tools for representing the water solubilities of these molecules.
引用
收藏
页码:3469 / 3476
页数:8
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共 44 条
  • [11] Statistical associating fluid theory: A successful model for the calculation of thermodynamic and phase equilibrium properties of complex fluid mixtures
    Economou, IG
    [J]. INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH, 2002, 41 (05) : 953 - 962
  • [12] Antioxidant and antigenotoxic effects of plant cell wall hydroxycinnamic acids in cultured HT-29 cells
    Ferguson, LR
    Zhu, ST
    Harris, PJ
    [J]. MOLECULAR NUTRITION & FOOD RESEARCH, 2005, 49 (06) : 585 - 593
  • [13] A new development in the application of the group contribution associating equation of state to model solid solubilities of phenolic compounds in SC-CO2
    Fornari, T
    Chafer, A
    Stateva, RP
    Reglero, G
    [J]. INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH, 2005, 44 (21) : 8147 - 8156
  • [14] Use of the DIPPR database for development of quantitative structure-property relationship correlations: Heat capacity of solid organic compounds
    Goodman, BT
    Wilding, WV
    Oscarson, JL
    Rowley, RL
    [J]. JOURNAL OF CHEMICAL AND ENGINEERING DATA, 2004, 49 (01) : 24 - 31
  • [15] VAPOR-LIQUID-EQUILIBRIA BY UNIFAC GROUP CONTRIBUTION .5. REVISION AND EXTENSION
    HANSEN, HK
    RASMUSSEN, P
    FREDENSLUND, A
    SCHILLER, M
    GMEHLING, J
    [J]. INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH, 1991, 30 (10) : 2352 - 2355
  • [16] Antiproliferative and apoptotic effects of selective phenolic acids on T47D human breast cancer cells: potential mechanisms of action
    Kampa, M
    Alexaki, VI
    Notas, G
    Nifli, AP
    Nistikaki, A
    Hatzoglou, A
    Bakogeorgou, E
    Kouimtzoglou, E
    Blekas, G
    Boskou, D
    Gravanis, A
    Castanas, E
    [J]. BREAST CANCER RESEARCH, 2004, 6 (02) : R63 - R74
  • [17] REACTION OF PARA-HYDROXYCINNAMIC ACID-DERIVATIVES WITH NITRITE AND ITS RELEVANCE TO NITROSAMINE FORMATION
    KIKUGAWA, K
    HAKAMADA, T
    HASUNUMA, M
    KURECHI, T
    [J]. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1983, 31 (04) : 780 - 785
  • [18] Estimation of the heat capacity of organic liquids as a function of temperature by a three-level group contribution method
    Kolska, Zdenka
    Kukal, Jaromir
    Zabransk, Milan
    Ruzicka, Vlastimil
    [J]. INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH, 2008, 47 (06) : 2075 - 2085
  • [19] Ten years with the CPA (Cubic-Plus-Association) equation of state. Part 1. Pure compounds and self-associating systems
    Kontogeorgis, Georgios M.
    Michelsen, Michael L.
    Folas, Georgios K.
    Derawi, Samer
    von Solms, Nicolas
    Stenby, Erling H.
    [J]. INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH, 2006, 45 (14) : 4855 - 4868
  • [20] Ten years with the CPA (Cubic-Plus-Association) equation of state. Part 2. Cross-associating and multicomponent systems
    Kontogeorgis, Georgios M.
    Michelsen, Michael L.
    Folas, Georgios K.
    Derawi, Samer
    von Solms, Nicolas
    Stenby, Erling H.
    [J]. INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH, 2006, 45 (14) : 4869 - 4878