Hostname: page-component-7479d7b7d-qlrfm Total loading time: 0 Render date: 2024-07-13T02:32:22.906Z Has data issue: false hasContentIssue false
  • English
  • Français

Thermotropic behavior of sodium cholesteryl carbonate

Published online by Cambridge University Press:  31 January 2011

Rabkwan Chuealee ,
Timothy S. Wiedmann  and
Teerapol Srichana
Rabkwan Chuealee
Affiliation:
Department of Pharmaceutical Technology, Faculty of Pharmaceutical Sciences, Prince of Songkla University, Hat Yai, Songkla 90112, Thailand
Timothy S. Wiedmann
Affiliation:
University of Minnesota, Department of Pharmaceutics, Minneapolis, Minnesota 55455
Teerapol Srichana*
Affiliation:
Department of Pharmaceutical Technology, Faculty of Pharmaceutical Sciences, Prince of Songkla University, Hat Yai, Songkla 90112, Thailand
*
a) Address all correspondence to this author. e-mail: teerapol.s@psu.ac.th
Get access

Abstract

Sodium cholesteryl carbonate ester (SCC) was synthesized, and its phase behavior was studied. The chemical structure was assessed by solid-state infrared spectroscopy based on vibration analysis. The wave number at 1705 and 1276 cm−1 corresponds to a carbonyl carbonate and O–C–O stretching of SCC, respectively. Molecular structure of SCC was further investigated with 1H and 13C NMR spectroscopy. The chemical shift, for the carbonyl carbonate resonance appeared at 155.5 ppm. A molecular mass of SCC was at m/z of 452. Differential scanning calorimetry (DSC), video-enhanced microscopy (VEM) together with polarized light microscopy, and small-angle x-ray scattering (SAXS) were used to characterize the phase behavior as a function of temperature of SCC. Liquid crystalline phase was formed with SCC. Based on the thermal properties and x-ray diffraction, it appears that SCC forms a structure analogous to the type II monolayer structure observed with cholesterol esters.

Keywords

Chemical synthesisNuclear magnetic resonance (NMR)X-ray diffraction (XRD)
Type
Articles
Information
Journal of Materials Research , Volume 24 , Issue 1 , January 2009 , pp. 156 - 163
Copyright
Copyright © Materials Research Society 2009

Access options

Get access to the full version of this content by using one of the access options below. (Log in options will check for institutional or personal access. Content may require purchase if you do not have access.)

References

REFERENCES

1.Tyle, P.: Liquid crystals and their applications in drug deliveryControlled Release of Drugs: Polymers and Aggregate Systems VCH Publisher, Inc New York 1988 25Google Scholar
2.Muller-Goymann, C.C.: Physicochemical characterization of colloidal drug delivery systems such as reverse micelles, vesicles, liquid crystals and nanoparticles for topical administration. Eur. J. Pharm. Biopharm 58, 343 2004CrossRefGoogle ScholarPubMed
3.Fairhurst, C.E., Fuller, S., Gray, J., Holmes, M.C., Tiddy, G.J.T.: Liquid Crystals Handbook Vol. 3, Wiley-VCH Verlag GmbH & Co KGaA, Germany 1998 341Google Scholar
4.Madhusudana, N.V.: Recent advances in thermotropic liquid crystals in special section: Soft condensed matter. Curr. Sci 80, 81018 2001Google Scholar
5.Hwang, J.J., Iyer, S.N., Li, L.S., Claussen, R., Harrington, D.A., Stupp, S.I.: Self-assembling biomaterials: Liquid crystal phases of cholesteryl oligo(l-lactic acid) and their interactions with cells. Proc. Natl. Acad. Sci. USA 99, 159662 2002CrossRefGoogle ScholarPubMed
6.Small, D.M.: Lipid Research Handbook: The Physical Chemistry of Lipids From Alkanes to Phospholipids Vol. 4, Plenum Press NY 1986 1Google Scholar
7.Lin, Y.Y., Chen, K.S., Lin, S.Y.: Thermophysical properties of cholesteryl oleyl carbonate determined with microscopic FTIR/DSC system. J. Chinese Chem. Soc. (Taipei) 42, 5865 1995Google Scholar
8.Lin, Y.Y., Tseng, H.Y., Li, M.J.: Phase studies and thermal stability of binary systems of cholesteric liquid crystals. Appl. Phys. A 70, 663 2000CrossRefGoogle Scholar
9.Ginsburg, G.S., Atkinson, D., Small, D.M.: Physical properties of cholesterol esters. Prog. Lipid Res 23, 135 1984CrossRefGoogle Scholar
10.Suh, I-H., Ko, T.S., Park, Y.J., Yoon, Y.K., Saenger, W.: Structure of cholesterol n-hexyl carbonate. Acta Crystallogr. C 44, 2163 1988Google Scholar
11.Croll, D.H., Sripada, P.K., Hamilton, J.A.: Temperature-dependent molecular motions and phase behavior of cholesteryl ester analogues. Lip. Res 28, 1444 1987CrossRefGoogle ScholarPubMed