Analogs of natural lipids. II. Polymorphic behavior of the tris- Homo acyl derivatives of cyclopentane-1,2,3-triols

• Published in: Chemistry and physics of lipids Vol. 18; no. 2; pp. 154 - 169
• Main Authors: Greenwald, S.M., Hancock, A.J., Sable, H.Z., D'esposito, L., Koenig, J.L.
• Format: Journal Article
• Language: English
• Published: Elsevier Ireland Ltd 1977
• ISSN: 0009-3084; 1873-2941
• DOI: 10.1016/0009-3084(77)90003-2

The polymorphic behavior of the three series of tris- homoacyl (C 14:0, C 16:0 and C 18:0) cyclopentane-1,2,3-triol analogs of the natural saturated triglycerides has been studied using differential thermal analysis, Fourier transform infrared spectroscopy, and X-ray diffraction. It was found that the triglyceride analogs derived from the 1,2,3/0 and 1,2/3 cyclopentanetriols exhibit different polymorphic behavior than that of the natural triglycerides. The analogs derived from 1,3/2 cyclopentanetriol, however, were found to parallel the polymorphic behavior of the natural triglycerides quite closely. This polymorphic behavior is discussed in terms of the different configurations which the chains assume in each of the triglyceride analogs.