(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.

Asaro, F., Boga, C., Demitri, N., De Zorzi, R., Drioli, S., Gigli, L., et al. (2019). X-Ray Crystal Structures and Organogelator Properties of (R)-9-Hydroxystearic Acid. MOLECULES, 24(15), 1-18 [10.3390/molecules24152854].

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

Boga, Carla
Membro del Collaboration Group
;
Micheletti, Gabriele
Membro del Collaboration Group
;
2019

Abstract

(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.
2019
Asaro, F., Boga, C., Demitri, N., De Zorzi, R., Drioli, S., Gigli, L., et al. (2019). X-Ray Crystal Structures and Organogelator Properties of (R)-9-Hydroxystearic Acid. MOLECULES, 24(15), 1-18 [10.3390/molecules24152854].
Asaro, Fioretta; Boga, Carla; Demitri, Nicola; De Zorzi, Rita; Drioli, Sara; Gigli, Lara; Micheletti, Gabriele; Nitti, Patrizia; Zangrando, Ennio...espandi
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11585/698036
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