The solubility and availability of progesterone 149
Figure 6. The inclusion method of β-cyclodextrin and progesterone.
stretching band at 2939.95 cmϪ1, peak 2, and a
C–H asymmetrical stretching band at 2854.13 cmϪ1,
peak 3. The absorption peaks 4 and 5 around
1698.28, 1662.34, and 1617.02 cmϪ1 are known to
be characteristic of carbonyl stretching vibration
(C-20 and C-3 position) and CϭC (C-4 position),
respectively. The absorption peaks around 1355
cmϪ1, peak 7, are characteristic of methyl groups.
The IR spectrum of β-CD (Figure 5b) displayed
a broad-stretching intense peak, 1, around 3396.99
cmϪ1 characteristic of a molecular hydrogen
bond, and an asymmetrical stretching C–H band
at 2924.52 cmϪ1, peak 2. Further, the bend C–H
bands peaks 5, 6, and 7 were at 1419, 1368.25, and
1338.25 cmϪ1, respectively.The C–O–C asymmetri-
cal stretching peak and α-1, four-band framework
vibration at 1031.73 and 854.311 cmϪ1, peaks 8
and 9, respectively, are displayed. Peaks 10, 11, and
12 at 754.031, 703.89 and 577.576 cmϪ1, respec-
tively, were characteristics for the stretching C–C
bands, two ring vibrations and framework vibration,
respectively.
The IR spectrum of the 1:1 inclusion complex
(Figure 5c) showed that the C–O–C asymmetrical
stretching peak and α-1, four-band framework
vibration at 1031.73 and 854.311 cmϪ1, from
peaks 10 to peak 12, were present, which indicated
that the structure of β-CD was not broken. More-
over, the stretching bands of the carbonyl group in
PR had disappeared. These spectral changes can be
explained by the dissociation of the intermolecular
hydrogen bonds of PR through inclusion complex-
ation (Uekama et al. 1982; Cerchiara et al. 2003).
Based on the DSC and IR spectrum, the ketone
groups of PR were completely included into the
hydrophobic cavity of β-CD (Figure 6) through ring
A (a) or D ring (b) in PR.
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Declaration of interest: The authors report no
declarations of interest.The authors alone are respon-
sible for the content and writing of the paper.