(αR,4R,4aR,6aS,7R,8S,10R,11S)-Methyl α-acet­oxy-4-(3-furan­yl)-10-hy­droxy-4a,7,9,9-tetra­methyl-2,13-dioxo-1,4,4a,5,6,6a,7,8,9,10,11,12-dodeca­hydro-7,11-methano-2H-cyclo­octa­[f][2]benzopyran-8-acetate (6-O-acetyl­swietenolide) from the seeds of Swietenia macrophylla

The mol­ecule of O-acetyl­swietenolide, C(29)H(36)O(9), isolated from the seeds of Swietenia macrophylla, features four six-membered rings connected together in the shape of a bowl; one of the inner rings adopts a twisted chair conformation owing to the C=C double bond. The furyl substitutent is con...

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Detalles Bibliográficos
Autores principales: Goh, Bey Hing, Abdul Kadir, Habsah, Abdul Malek, Sri Nurestri, Ng, Seik Weng
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2010
Materias:
Organic Papers
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3009069/
https://www.ncbi.nlm.nih.gov/pubmed/21588997
http://dx.doi.org/10.1107/S1600536810039942
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author Goh, Bey Hing
Abdul Kadir, Habsah
Abdul Malek, Sri Nurestri
Ng, Seik Weng
author_facet Goh, Bey Hing
Abdul Kadir, Habsah
Abdul Malek, Sri Nurestri
Ng, Seik Weng
author_sort Goh, Bey Hing
collection PubMed
description The mol­ecule of O-acetyl­swietenolide, C(29)H(36)O(9), isolated from the seeds of Swietenia macrophylla, features four six-membered rings connected together in the shape of a bowl; one of the inner rings adopts a twisted chair conformation owing to the C=C double bond. The furyl substitutent is connected to an outer ring, and it points away from the bowl cavity. The hy­droxy group is connected to a carbonyl O atom of an adjacent mol­ecule by an O—H⋯O hydrogen bond, generating a chain running along the b axis.
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spelling pubmed-30090692010-12-30 (αR,4R,4aR,6aS,7R,8S,10R,11S)-Methyl α-acet­oxy-4-(3-furan­yl)-10-hy­droxy-4a,7,9,9-tetra­methyl-2,13-dioxo-1,4,4a,5,6,6a,7,8,9,10,11,12-dodeca­hydro-7,11-methano-2H-cyclo­octa­[f][2]benzopyran-8-acetate (6-O-acetyl­swietenolide) from the seeds of Swietenia macrophylla Goh, Bey Hing Abdul Kadir, Habsah Abdul Malek, Sri Nurestri Ng, Seik Weng Acta Crystallogr Sect E Struct Rep Online Organic Papers The mol­ecule of O-acetyl­swietenolide, C(29)H(36)O(9), isolated from the seeds of Swietenia macrophylla, features four six-membered rings connected together in the shape of a bowl; one of the inner rings adopts a twisted chair conformation owing to the C=C double bond. The furyl substitutent is connected to an outer ring, and it points away from the bowl cavity. The hy­droxy group is connected to a carbonyl O atom of an adjacent mol­ecule by an O—H⋯O hydrogen bond, generating a chain running along the b axis. International Union of Crystallography 2010-10-13 /pmc/articles/PMC3009069/ /pubmed/21588997 http://dx.doi.org/10.1107/S1600536810039942 Text en © Goh 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
Goh, Bey Hing
Abdul Kadir, Habsah
Abdul Malek, Sri Nurestri
Ng, Seik Weng
(αR,4R,4aR,6aS,7R,8S,10R,11S)-Methyl α-acet­oxy-4-(3-furan­yl)-10-hy­droxy-4a,7,9,9-tetra­methyl-2,13-dioxo-1,4,4a,5,6,6a,7,8,9,10,11,12-dodeca­hydro-7,11-methano-2H-cyclo­octa­[f][2]benzopyran-8-acetate (6-O-acetyl­swietenolide) from the seeds of Swietenia macrophylla
title (αR,4R,4aR,6aS,7R,8S,10R,11S)-Methyl α-acet­oxy-4-(3-furan­yl)-10-hy­droxy-4a,7,9,9-tetra­methyl-2,13-dioxo-1,4,4a,5,6,6a,7,8,9,10,11,12-dodeca­hydro-7,11-methano-2H-cyclo­octa­[f][2]benzopyran-8-acetate (6-O-acetyl­swietenolide) from the seeds of Swietenia macrophylla
title_full (αR,4R,4aR,6aS,7R,8S,10R,11S)-Methyl α-acet­oxy-4-(3-furan­yl)-10-hy­droxy-4a,7,9,9-tetra­methyl-2,13-dioxo-1,4,4a,5,6,6a,7,8,9,10,11,12-dodeca­hydro-7,11-methano-2H-cyclo­octa­[f][2]benzopyran-8-acetate (6-O-acetyl­swietenolide) from the seeds of Swietenia macrophylla
title_fullStr (αR,4R,4aR,6aS,7R,8S,10R,11S)-Methyl α-acet­oxy-4-(3-furan­yl)-10-hy­droxy-4a,7,9,9-tetra­methyl-2,13-dioxo-1,4,4a,5,6,6a,7,8,9,10,11,12-dodeca­hydro-7,11-methano-2H-cyclo­octa­[f][2]benzopyran-8-acetate (6-O-acetyl­swietenolide) from the seeds of Swietenia macrophylla
title_full_unstemmed (αR,4R,4aR,6aS,7R,8S,10R,11S)-Methyl α-acet­oxy-4-(3-furan­yl)-10-hy­droxy-4a,7,9,9-tetra­methyl-2,13-dioxo-1,4,4a,5,6,6a,7,8,9,10,11,12-dodeca­hydro-7,11-methano-2H-cyclo­octa­[f][2]benzopyran-8-acetate (6-O-acetyl­swietenolide) from the seeds of Swietenia macrophylla
title_short (αR,4R,4aR,6aS,7R,8S,10R,11S)-Methyl α-acet­oxy-4-(3-furan­yl)-10-hy­droxy-4a,7,9,9-tetra­methyl-2,13-dioxo-1,4,4a,5,6,6a,7,8,9,10,11,12-dodeca­hydro-7,11-methano-2H-cyclo­octa­[f][2]benzopyran-8-acetate (6-O-acetyl­swietenolide) from the seeds of Swietenia macrophylla
title_sort (αr,4r,4ar,6as,7r,8s,10r,11s)-methyl α-acet­oxy-4-(3-furan­yl)-10-hy­droxy-4a,7,9,9-tetra­methyl-2,13-dioxo-1,4,4a,5,6,6a,7,8,9,10,11,12-dodeca­hydro-7,11-methano-2h-cyclo­octa­[f][2]benzopyran-8-acetate (6-o-acetyl­swietenolide) from the seeds of swietenia macrophylla
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3009069/
https://www.ncbi.nlm.nih.gov/pubmed/21588997
http://dx.doi.org/10.1107/S1600536810039942
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