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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...

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Detalles Bibliográficos
Autores principales: Gaware, Rawindra, Czollner, Laszlo, Jordis, Ulrich, Mereiter, Kurt
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2010
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°.
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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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AT jordisulrich methyl3bacetoxy13carboxy19hydroxy11oxocnorolean18en30oateglactone
AT mereiterkurt methyl3bacetoxy13carboxy19hydroxy11oxocnorolean18en30oateglactone