Journal of Thermal Analysis and Calorimetry

, Volume 122, Issue 1, pp 55–64 | Cite as

Thermal analysis and simulation model of natural lithocholic acid

  • A. Rudzki
  • M. D. Ossowska-Chruściel
  • M. Ordon
  • W. Zając
  • J. Chruściel
Article
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Accepted:

Abstract

Thermal behaviour of pure lithocholic acid was studied in a broad temperature range, from −20 to 200 °C, using several complementary methods. The temperatures of phase transition were determined, as well as decomposition temperature. Spectroscopic differences between the stable phase and the glass state were shown and explained as resulting from different networks of hydrogen bonds. The influence of the cooling rate on the rate of the glass formation was determined. Quantum chemical calculations were performed in order to support the above conclusion.

Keywords

Lithocholic acid Thermal behaviour Phase transitions Glass state Thermal stability Intermolecular interactions 
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References

  1. 1.
    Arora SK, Germain G, Declercq JP. The crystal and molecular structure of lithocholic acid. Acta Crystallogr. 1976;B32:415–9.CrossRefGoogle Scholar
  2. 2.
    Hofmann AF, Mysels KJ. Bile acid solubility and precipitation in vitro and in vivo: the role of conjugation, pH, and Ca2+ ions. J Lipid Res. 1992;33:617–26.Google Scholar
  3. 3.
    Steiner C, von Eckardstein A, Rentsch KM. Quantification of the 15 major human bile acids and their precursor 7-hydroxy-4-cholesten-3-one in serum by liquid chromatography–tandem mass spectrometry. J Chromatogr B. 2010;878:2870–80.CrossRefGoogle Scholar
  4. 4.
    He S, Liang WW, Tanner C, Cheng K-L, Fang J, Wu S-T. Liquid crystal based sensors for the detection of cholic acid. Anal Methods. 2013;5:4126–30.CrossRefGoogle Scholar
  5. 5.
    Pyka A, Dołowy M. Application of structural descriptors for the evaluation of some physicochemical properties of selected bile acids. Acta Pol Pharm. 2004;61:407–13.Google Scholar
  6. 6.
    Ishizawa M, Matsunawa M, Adachi R, Uno S, Ikeda K, Masuno H, Shimizu M, Iwasaki K-I, Yamada S, Makishima M. Lithocholic acid derivatives act as selective vitamin D receptor modulators without inducing hypercalcemia. J Lipid Res. 2008;49:763–72.CrossRefGoogle Scholar
  7. 7.
    Roleira FMF, Tavares da Silva EJ, Carvalho RA, Marques MPM. Lithocholic acid derivative as a model for artificial receptors: a Raman study. Lett Drug Des Discov. 2010;7:610–7.CrossRefGoogle Scholar
  8. 8.
    Tamhane K. Formation of lyotropic liquid crystals through the self-assembly of bile acid building blocks. Thesis; 2009.Google Scholar
  9. 9.
    Shaikh VAE, Maldar NN, Lonikar SV. Synthesis and mesomorphic behaviour of lithocholic acid derivatives. Bull Mater Sci. 2003;26:559–63.CrossRefGoogle Scholar
  10. 10.
    Ossowska-Chruściel MD, Zalewski S, Rudzki A, Filiks A. The phase behaviour of 4-n-pentylphenyl-4′-n-heptyloxythiobenzoate. Phase Transit. 2006;79:679–90.CrossRefGoogle Scholar
  11. 11.
    Gross KC, Seybold PG, Hadad CM. Comparison of different atomic charge schemes for predicting pK a variations in substituted anilines and phenols. Int J Quantum Chem. 2002;90:445–58.CrossRefGoogle Scholar
  12. 12.
    Menczel JD. The rigid amorphous fraction in semicrystalline macromolecules. J Therm Anal Calorim. 2011;106:7–24.CrossRefGoogle Scholar
  13. 13.
    Danch A. The glass transition, finite size effect. J Therm Anal Calorim. 2006;84:663–8.CrossRefGoogle Scholar
  14. 14.
    Louar W, Meniai AH, Grolier JPE. Thermal analysis of the influence of water content on glass transitions. J Therm Anal Calorim. 2008;98:605–10.CrossRefGoogle Scholar
  15. 15.
    Jeffrey GA. An introduction to hydrogen bonding. New York: Oxford University Press; 1997.Google Scholar
  16. 16.
    Marechal Y. IR spectra of carboxylic acids in the gas phase: a quantitative reinvestigation. J Chem Phys. 1987;87:6344–53.CrossRefGoogle Scholar
  17. 17.
    Flakus HT, Hachuła B. Effects of “excessive” exciton interactions in polarized IR spectra of the hydrogen bond in 2-butynoic acid crystals. Proton transfer induced by dynamical co-operative interactions involving hydrogen bonds. Chem Phys. 2008;345:49–64.CrossRefGoogle Scholar
  18. 18.
    Flakus HT, Jabłońska M, Kusz J. An anomalous linear dichroic effect in the polarized IR spectra of 2-furancarboxylic acid crystals: proton transfer induced by co-operative interactions involving hydrogen bonds. Vib Spectrosc. 2009;49:174–82.CrossRefGoogle Scholar
  19. 19.
    University of Karlsruhe and Forschungszentrum Karlsruhe GmbH, 1989–2007, TURBOMOLE GmbH package, V6.5 and V6.6.Google Scholar
  20. 20.
    Ossowska-Chruściel MD, Juszyńska-Gałązka E, Zając W, Rudzki A, Chruściel J. Mesomorphic properties of resorcinol, 2014. J Mol Struct. 2015;1082:103–13.CrossRefGoogle Scholar
  21. 21.
    Frisch MJ, Trucks GW, Schlegel HB, et al. Gaussian 09, Revision D.01. Wallingford, CT: Gaussian, Inc.; 2013.Google Scholar

Copyright information

© Akadémiai Kiadó, Budapest, Hungary 2015

Authors and Affiliations

  • A. Rudzki
    • 1
  • M. D. Ossowska-Chruściel
    • 1
  • M. Ordon
    • 1
    • 2
  • W. Zając
    • 3
  • J. Chruściel
    • 1
  1. 1.Institute of ChemistrySiedlce University of Natural Sciences and HumanitiesSiedlcePoland
  2. 2.Laboratory of Neutron PhysicsJoint Institute for Nuclear ResearchDubnaRussian Federation
  3. 3.Institute of Nuclear PhysicsPolish Academy of SciencesKrakówPoland

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