(<i>R</i>)-10-Hydroxystearic Acid: Crystals vs. Organogel
The chiral (<i>R</i>)-10-hydroxystearic acid ((<i>R</i>)-10-HSA) is a positional homologue of both (<i>R</i>)-12-HSA and (<i>R</i>)-9-HSA with the OH group in an intermediate position. While (<i>R</i>)-12-HSA is one of the best-known low-mo...
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doaj-347240f5ddab4e659f1d48a1d2fe16f92020-11-25T03:36:38ZengMDPI AGInternational Journal of Molecular Sciences1661-65961422-00672020-10-01218124812410.3390/ijms21218124(<i>R</i>)-10-Hydroxystearic Acid: Crystals vs. OrganogelFioretta Asaro0Carla Boga1Rita De Zorzi2Silvano Geremia3Lara Gigli4Patrizia Nitti5Sabrina Semeraro6Department of Chemical and Pharmaceutical Sciences, University of Trieste, via L. Giorgieri 1, 34127 Trieste, ItalyDepartment of Industrial Chemistry “Toso Montanari”, University of Bologna, Viale del Risorgimento 4, 40136 Bologna, ItalyDepartment of Chemical and Pharmaceutical Sciences, University of Trieste, via L. Giorgieri 1, 34127 Trieste, ItalyDepartment of Chemical and Pharmaceutical Sciences, University of Trieste, via L. Giorgieri 1, 34127 Trieste, ItalyElettra–Sincrotrone Trieste, S.S. 14 Km 163.5 in Area Science Park, Basovizza, 34149 Trieste, ItalyDepartment of Chemical and Pharmaceutical Sciences, University of Trieste, via L. Giorgieri 1, 34127 Trieste, ItalyDepartment of Chemical and Pharmaceutical Sciences, University of Trieste, via L. Giorgieri 1, 34127 Trieste, ItalyThe chiral (<i>R</i>)-10-hydroxystearic acid ((<i>R</i>)-10-HSA) is a positional homologue of both (<i>R</i>)-12-HSA and (<i>R</i>)-9-HSA with the OH group in an intermediate position. While (<i>R</i>)-12-HSA is one of the best-known low-molecular-weight organogelators, (<i>R</i>)-9-HSA is not, but it forms crystals in several solvents. With the aim to gain information on the structural role of hydrogen-bonding interactions of the carbinol OH groups, we investigated the behavior of (<i>R</i>)-10-HSA in various solvents. This isomer displays an intermediate behavior between (<i>R</i>)-9 and (<i>R</i>)-12-HSA, producing a stable gel exclusively in paraffin oil, while it crystallizes in other organic solvents. Here, we report the X-ray structure of a single crystal of (<i>R</i>)-10-HSA as well as some structural information on its polymorphism, obtained through X-ray Powder Diffraction (XRPD) and Infrared Spectroscopy (IR). This case study provides new elements to elucidate the structural determinants of the microscopic architectures that lead to the formation of organogels of stearic acid derivatives.https://www.mdpi.com/1422-0067/21/21/8124crystal structureIR spectroscopyorganogel(<i>R</i>)-hydroxystearic acidpolymorphismX-ray diffraction |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Fioretta Asaro Carla Boga Rita De Zorzi Silvano Geremia Lara Gigli Patrizia Nitti Sabrina Semeraro |
spellingShingle |
Fioretta Asaro Carla Boga Rita De Zorzi Silvano Geremia Lara Gigli Patrizia Nitti Sabrina Semeraro (<i>R</i>)-10-Hydroxystearic Acid: Crystals vs. Organogel International Journal of Molecular Sciences crystal structure IR spectroscopy organogel (<i>R</i>)-hydroxystearic acid polymorphism X-ray diffraction |
author_facet |
Fioretta Asaro Carla Boga Rita De Zorzi Silvano Geremia Lara Gigli Patrizia Nitti Sabrina Semeraro |
author_sort |
Fioretta Asaro |
title |
(<i>R</i>)-10-Hydroxystearic Acid: Crystals vs. Organogel |
title_short |
(<i>R</i>)-10-Hydroxystearic Acid: Crystals vs. Organogel |
title_full |
(<i>R</i>)-10-Hydroxystearic Acid: Crystals vs. Organogel |
title_fullStr |
(<i>R</i>)-10-Hydroxystearic Acid: Crystals vs. Organogel |
title_full_unstemmed |
(<i>R</i>)-10-Hydroxystearic Acid: Crystals vs. Organogel |
title_sort |
(<i>r</i>)-10-hydroxystearic acid: crystals vs. organogel |
publisher |
MDPI AG |
series |
International Journal of Molecular Sciences |
issn |
1661-6596 1422-0067 |
publishDate |
2020-10-01 |
description |
The chiral (<i>R</i>)-10-hydroxystearic acid ((<i>R</i>)-10-HSA) is a positional homologue of both (<i>R</i>)-12-HSA and (<i>R</i>)-9-HSA with the OH group in an intermediate position. While (<i>R</i>)-12-HSA is one of the best-known low-molecular-weight organogelators, (<i>R</i>)-9-HSA is not, but it forms crystals in several solvents. With the aim to gain information on the structural role of hydrogen-bonding interactions of the carbinol OH groups, we investigated the behavior of (<i>R</i>)-10-HSA in various solvents. This isomer displays an intermediate behavior between (<i>R</i>)-9 and (<i>R</i>)-12-HSA, producing a stable gel exclusively in paraffin oil, while it crystallizes in other organic solvents. Here, we report the X-ray structure of a single crystal of (<i>R</i>)-10-HSA as well as some structural information on its polymorphism, obtained through X-ray Powder Diffraction (XRPD) and Infrared Spectroscopy (IR). This case study provides new elements to elucidate the structural determinants of the microscopic architectures that lead to the formation of organogels of stearic acid derivatives. |
topic |
crystal structure IR spectroscopy organogel (<i>R</i>)-hydroxystearic acid polymorphism X-ray diffraction |
url |
https://www.mdpi.com/1422-0067/21/21/8124 |
work_keys_str_mv |
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