Skip to main content
SpringerLink
Log in

Molecular inclusion of butylated hydroxyanisole (BHA) into alpha and beta cyclodextrins

  • Original Article
  • Published:
Journal of Inclusion Phenomena and Macrocyclic Chemistry Aims and scope Submit manuscript

Abstract

BHA (butylated hydroxyanisole) was complexed with α- and β-cyclodextrins with the objective of characterizing the thermal stability. From phase solubility diagrams, the association constants for the complexes of α-CD:BHA and β-CD:BHA were found as 49.3 and 585 L mol−1, respectively. To increase the thermal stability of BHA, its molecular encapsulation in α-CD and β-CD, was tested using molar ratios of 1:1 and 1:2 (BHA:CD) and the complex preparation techniques of kneading and physical mixture. The products of complexation were characterized by differential scanning calorimetry and thermogravimetry, indicating the formation of a BHA:β-CD complex and showing that the release of the complexed BHA occurs in the temperature range of 280–350 °C, well above the temperature at which BHA sublimates. Dissolution tests have shown that the BHA: β-CD complex produced by kneading has high efficiency of dissolution and partition coefficient experiments demonstrated that the presence of β-CD leads to higher concentration of BHA in the organic phase.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9
Fig. 10
Fig. 11
Fig. 12
Fig. 13

Similar content being viewed by others

References

  1. National Toxicology Program, Eleventh Report on Carcinogens.: Butylated hydroxyanisole (BHA) CAS no. 25013-16-5. http://ntp.niehs.nih.gov/ntp/roc/eleventh/profiles/s027bha.pdf (2009). Accessed 27 Feb 2009

  2. Williams, G.M., Iatropoulos, M.J., Whysner, J.: Safety assessment of butylated hydroxyanisole and butylated hydroxytoluene as antioxidant food additives. Food Chem. Toxicol. 37(9–10), 1027–1038 (1999)

    CAS  Google Scholar 

  3. Ramalho, V., Jorge, N.: Antioxidantes utilizados em óleos, gorduras e alimentos gordurosos. Quim. Nova 29(4), 755–760 (2006)

    Article  CAS  Google Scholar 

  4. Szejtli, J., Szente, L.: Cyclodextrins as food ingredients. Food Sci. Technol. 15, 137–142 (2004)

    Article  Google Scholar 

  5. Vora, J., Boroujerdi, M.: Enhanced aqueous solubility of phenolic antioxidants using modified β-cyclodextrins. Drug Dev. Ind. Pharm. 21, 495–502 (1995)

    Article  CAS  Google Scholar 

  6. Higuchi, T., Connors, K.A.: Phase Solubility Techniques (Advances in Analytical Chemistry and Instrumentation), pp. 117–212. Wiley Interscience, New York (1965)

    Google Scholar 

  7. Khan, K.A., Rhodes, C.T.: The concept of dissolution efficiency. J. Pharm. Pharmacol. Wallingford 27, 48–49 (1975)

    CAS  Google Scholar 

  8. Bekers, O., Uijtendaal, E.V., Beijnen, J.H., Bult, A., Underberg, W.J.M.: Cyclodextrins in the pharmaceutical field. Drug Dev. Ind. Pharm. 17, 1503–1549 (1991)

    Article  CAS  Google Scholar 

  9. Zia, V., Rajewski, R.A., Stella, V.J.: Effect of cyclodextrin charge on complexation of neutral and charged substrates: comparison of sulfobutyl ether-β-cyclodextrin to hydroxypropyl β-cyclodextrin. Pharm. Res. 18(5), 667–673 (2001)

    Article  CAS  Google Scholar 

  10. Archontaki, H., Vertzoni, M., Athanassiou-Malaki, M.: Study on the inclusion complexes of bromazepam with β and β-hydroxypropyl-cyclodextrins. J. Pharm. Biomed. Anal. 28, 761–769 (2002)

    Article  CAS  Google Scholar 

  11. Yilmaz, V.T., Karadag, A., Içbudak, H.: Thermal decomposition of β-cyclodextrin inclusion complexes of ferrocene and their derivatives. Thermochim. Acta 261, 107–118 (1995)

    Article  CAS  Google Scholar 

  12. Rama, A.C.R., Veiga, F., Figueiredo, I.V., Souza, A., Caramona, M.: Complexos de inclusão de indometacina com hidroxipropil-β-ciclodextrina. Estudos de dissolução e coeficiente de partição. Braz. J. Pharm. Sci. 42(1), 59–68 (2006)

    CAS  Google Scholar 

  13. Frijlink, H.W., Schoonen, A.J.M., Lerk, C.F.: The effects of cyclodextrins on drug absorption I: in vitro observations. Int. J. Pharm. Amst. 49, 91–102 (1989)

    Article  CAS  Google Scholar 

  14. Nakajima, T., Sunagawa, M., Hirohashi, T.: Studies of cyclodextrin inclusion complexes. II. Application of the partition coefficient method. Chem. Pharm. Bull. Tokyo 32(2), 401–408 (1984)

    CAS  Google Scholar 

  15. Uekama, K., Uemura, Y., Irie, T., Otagiri, M.: Analysis of interfacial transfer and absorption behaviour of drugs following dissolution from β-cyclodextrin complexes. Chem. Pharm. Bull. Tokyo 31(10), 3637–3643 (1983)

    CAS  Google Scholar 

Download references

Acknowledgments

We are grateful to the supporting institutions: CAPES (Coordenação de Aperfeiçoamento de Pessoal de Nível Superior) and UEM (Universidade Estadual de Maringá).

Author information

Authors and Affiliations

  1. Departamento de Engenharia Química, Universidade Estadual de Maringá, Av. Colombo 5790, Maringá, PR, CEP 87020-900, Brazil

    Carlos Eduardo Barão, Gisella Maria Zanin & Flavio Faria de Moraes

Authors
  1. Carlos Eduardo Barão
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Gisella Maria Zanin
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Flavio Faria de Moraes
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Carlos Eduardo Barão.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Barão, C.E., Zanin, G.M. & de Moraes, F.F. Molecular inclusion of butylated hydroxyanisole (BHA) into alpha and beta cyclodextrins. J Incl Phenom Macrocycl Chem 71, 179–187 (2011). https://doi.org/10.1007/s10847-011-9925-6

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10847-011-9925-6

Keywords

Search

Navigation