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(+)-Methyl 3β-acetoxy-13-carboxy-19-hydroxy-11-oxo-C-norolean-18-en-30-oate γ-lactone
The title compound, C(33)H(46)O(7), is an unusual oxydation product of the therapeutic agent glycyrrhetinic acid that has, in comparison to the latter, a distinctly altered triterpene structure with one five- and four six-membered carbocycles complemented by a γ-lactone ring with a spiro-junction an...
Autores principales: | , , , |
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Formato: | Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2010
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2983216/ https://www.ncbi.nlm.nih.gov/pubmed/21587575 http://dx.doi.org/10.1107/S1600536810036901 |
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author | Gaware, Rawindra Czollner, Laszlo Jordis, Ulrich Mereiter, Kurt |
author_facet | Gaware, Rawindra Czollner, Laszlo Jordis, Ulrich Mereiter, Kurt |
author_sort | Gaware, Rawindra |
collection | PubMed |
description | The title compound, C(33)H(46)O(7), is an unusual oxydation product of the therapeutic agent glycyrrhetinic acid that has, in comparison to the latter, a distinctly altered triterpene structure with one five- and four six-membered carbocycles complemented by a γ-lactone ring with a spiro-junction and a ring double bond. The junction between the five-membered ring C, a cyclopentanone ring, and the six-membered ring D, previously in question, was found to be cis, confirming earlier structure assignments based solely on chemical transformations. In the solid state, the compound exhibits five intra- and four intermolecular C—H⋯O interactions with H⋯O distances less than or equal to 2.70 Å and C—H⋯O greater than 100°. |
format | Text |
id | pubmed-2983216 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2010 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-29832162010-12-30 (+)-Methyl 3β-acetoxy-13-carboxy-19-hydroxy-11-oxo-C-norolean-18-en-30-oate γ-lactone Gaware, Rawindra Czollner, Laszlo Jordis, Ulrich Mereiter, Kurt Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(33)H(46)O(7), is an unusual oxydation product of the therapeutic agent glycyrrhetinic acid that has, in comparison to the latter, a distinctly altered triterpene structure with one five- and four six-membered carbocycles complemented by a γ-lactone ring with a spiro-junction and a ring double bond. The junction between the five-membered ring C, a cyclopentanone ring, and the six-membered ring D, previously in question, was found to be cis, confirming earlier structure assignments based solely on chemical transformations. In the solid state, the compound exhibits five intra- and four intermolecular C—H⋯O interactions with H⋯O distances less than or equal to 2.70 Å and C—H⋯O greater than 100°. International Union of Crystallography 2010-09-18 /pmc/articles/PMC2983216/ /pubmed/21587575 http://dx.doi.org/10.1107/S1600536810036901 Text en © Gaware et al. 2010 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited. |
spellingShingle | Organic Papers Gaware, Rawindra Czollner, Laszlo Jordis, Ulrich Mereiter, Kurt (+)-Methyl 3β-acetoxy-13-carboxy-19-hydroxy-11-oxo-C-norolean-18-en-30-oate γ-lactone |
title | (+)-Methyl 3β-acetoxy-13-carboxy-19-hydroxy-11-oxo-C-norolean-18-en-30-oate γ-lactone |
title_full | (+)-Methyl 3β-acetoxy-13-carboxy-19-hydroxy-11-oxo-C-norolean-18-en-30-oate γ-lactone |
title_fullStr | (+)-Methyl 3β-acetoxy-13-carboxy-19-hydroxy-11-oxo-C-norolean-18-en-30-oate γ-lactone |
title_full_unstemmed | (+)-Methyl 3β-acetoxy-13-carboxy-19-hydroxy-11-oxo-C-norolean-18-en-30-oate γ-lactone |
title_short | (+)-Methyl 3β-acetoxy-13-carboxy-19-hydroxy-11-oxo-C-norolean-18-en-30-oate γ-lactone |
title_sort | (+)-methyl 3β-acetoxy-13-carboxy-19-hydroxy-11-oxo-c-norolean-18-en-30-oate γ-lactone |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2983216/ https://www.ncbi.nlm.nih.gov/pubmed/21587575 http://dx.doi.org/10.1107/S1600536810036901 |
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