X-Ray Crystal Structures and Organogelator Properties of (R)-9-Hydroxystearic Acid

Molecules

Patrizia Nitti¹  Ennio Zangrando¹  Rita De Zorzi¹  Fioretta Asaro¹  Sara Drioli¹  Gabriele Micheletti²  Carla Boga²  Nicola Demitri³  Lara Gigli³ 

[1]Department of Chemical and Pharmaceutical Sciences, University of Trieste, via L. Giorgieri 1, 34127 Trieste, Italy

[2]Department of Industrial Chemistry “Toso Montanari”, University of Bologna, viale del Risorgimento 4, 40136 Bologna, Italy

[3]Elettra–Sincrotrone Trieste, S.S. 14 Km 163.5 in Area Science Park, Basovizza, 34149 Trieste, Italy

关键词: organogel;    chirality;    self-assembly;    hydrogen bond;    polymorphs;    X-ray diffraction;    rheology;   

DOI  :  10.3390/molecules24152854

来源: DOAJ

【 摘 要 】

(R)-9-hydroxystearic acid, (R)-9-HSA, is a chiral nonracemic hydroxyacid of natural origin possessing interesting properties as an antiproliferative agent against different cancer types. Considering its potential application for medical and pharmaceutical purposes, the structures and rheological properties of (R)-9-HSA were investigated. Oscillatory rheology measurements reveal that (R)-9-HSA gels only paraffin oil, with less efficiency and thermal stability than its positional isomer (R)-12-HSA. Conversely, (R)-9-HSA affords crystals from methanol, acetonitrile, and carbon tetrachloride. The single crystal structures obtained both at 293 K and 100 K show non-centrosymmetric twisted carboxylic acid dimers linked at the midchain OHs into long, unidirectional chains of hydrogen bonds, owing to head-tail ordering of the molecules. Synchrotron X-ray powder diffraction experiments, performed on the solids obtained from different solvents, show the occurrence of polymorphism in paraffin oil and through thermal treatment of the solid from methanol.

【 授权许可】

Unknown