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

Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry
Fioretta AsaroEnnio Zangrando

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.

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Citations

Nov 5, 2020·International Journal of Molecular Sciences·Fioretta AsaroSabrina Semeraro

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Methods Mentioned

BETA
X-ray
rheology
circular dichroism
thermal treatment
PCR

Software Mentioned

EXPO2014
TOPAS
rSpace
SHELXL
XDS
Academic
Coelho

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