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Tracking of enantioselective solubility of rac ‐norgestrel in the presence of cyclodextrin by a CD spectroscopic method
Author(s) -
Szegvári Dávid,
Zelkó Romána,
Horváth Péter,
Gergely András
Publication year - 2005
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.20224
Subject(s) - chemistry , enantiomer , cyclodextrin , chirality (physics) , solubility , circular dichroism , dissolution , aqueous solution , chromatography , molecule , enantioselective synthesis , inclusion compound , crystallography , stereochemistry , organic chemistry , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , quark , catalysis
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. © 2005 Wiley‐Liss, Inc. Chirality 18:121–126, 2006.