Tracking of enantioselective solubility of rac-norgestrel in the presence of cyclodextrin by a CD spectroscopic method

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6 Citations (Scopus)

Abstract

Dissolution of Hydrophobic rac-norgestrel in aqueous γ-cyclodextrin (γ-CyD) and hydroxypropyl-γ-cyclodextrin (HP-γ-CyD) solutions was investigated, and enantioselective dissolution was observed. (-)-Norgestrel, the eutomer molecule, was dissolved to a greater extent using each of the CyDs, although the effect was more significant in the case of HP-γ-CyD. A circular dichroism (CD) spectroscopic method based on measurement of the anisotropy factor was applied for the determination of the enantiomer ratio. The concentration and the enantiomer ratio of norgestrel were determined indirectly in octanol after extraction. Optical rotation dispersion (ORD) measurements could confirm that neither the free CyDs nor their inclusion complexes could get into the organic phase during transport to octanol. Only the norgestrel molecules were able to get into the organic phase, although the enantiomer ratio remained the same as was obtained in the aqueous CyD solution.

Original languageEnglish
Pages (from-to)121-126
Number of pages6
JournalChirality
Volume18
Issue number2
DOIs
Publication statusPublished - Feb 7 2006

Keywords

  • Circular dichroism
  • Enantioselective dissolution
  • HP-γ-cyclodextrin
  • Inclusion complexes
  • Norgestrel
  • Phase-solubility study
  • γ-cyclodextrin

ASJC Scopus subject areas

  • Analytical Chemistry
  • Catalysis
  • Pharmacology
  • Drug Discovery
  • Spectroscopy
  • Organic Chemistry

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