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Xyloccensin E

The title compound (also known as phragmalin triacetate), C(35)H(42)O(14), is a phragmalin-type limonoid extracted from X. rumphii. The mol­ecule consists of eight rings with the orthoacetate group bridged at positions 1, 8 and 9. The two five-carbocyclic rings (A (1) and A (2)) and the dioxolane ri...

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Autores principales: Sarigaputi, Chanin, Teerawatananond, Thapong, Pengpreecha, Somchai, Muangsin, Nongnuj, Pudhom, Khanitha
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2010
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2979606/
https://www.ncbi.nlm.nih.gov/pubmed/21579436
http://dx.doi.org/10.1107/S1600536810016582
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author Sarigaputi, Chanin
Teerawatananond, Thapong
Pengpreecha, Somchai
Muangsin, Nongnuj
Pudhom, Khanitha
author_facet Sarigaputi, Chanin
Teerawatananond, Thapong
Pengpreecha, Somchai
Muangsin, Nongnuj
Pudhom, Khanitha
author_sort Sarigaputi, Chanin
collection PubMed
description The title compound (also known as phragmalin triacetate), C(35)H(42)O(14), is a phragmalin-type limonoid extracted from X. rumphii. The mol­ecule consists of eight rings with the orthoacetate group bridged at positions 1, 8 and 9. The two five-carbocyclic rings (A (1) and A (2)) and the dioxolane ring (G) adopt a distorted envelope conformation. The 1,3-dioxane ring (E) exists in a chair conformation. The six-carbocyclic rings (B and C) exhibit a twisted-boat conformation. The lactone ring has a half-chair conformation and the furan ring is planar (r.m.s. deviation = 0.002 Å). Rings A (1)/B, A (2)/B, B/C, C/D and C/G are all cis-fused. The two acet­oxy groups attached to ring B and the furan ring attached to the lactone ring are in equatorial positions. The porous crystal packing exhibits voids of 688 Å(3) and weak inter­molecular C—H⋯O inter­actions. The absolute configuration was assigned on the basis of literature data.
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spelling pubmed-29796062010-12-30 Xyloccensin E Sarigaputi, Chanin Teerawatananond, Thapong Pengpreecha, Somchai Muangsin, Nongnuj Pudhom, Khanitha Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound (also known as phragmalin triacetate), C(35)H(42)O(14), is a phragmalin-type limonoid extracted from X. rumphii. The mol­ecule consists of eight rings with the orthoacetate group bridged at positions 1, 8 and 9. The two five-carbocyclic rings (A (1) and A (2)) and the dioxolane ring (G) adopt a distorted envelope conformation. The 1,3-dioxane ring (E) exists in a chair conformation. The six-carbocyclic rings (B and C) exhibit a twisted-boat conformation. The lactone ring has a half-chair conformation and the furan ring is planar (r.m.s. deviation = 0.002 Å). Rings A (1)/B, A (2)/B, B/C, C/D and C/G are all cis-fused. The two acet­oxy groups attached to ring B and the furan ring attached to the lactone ring are in equatorial positions. The porous crystal packing exhibits voids of 688 Å(3) and weak inter­molecular C—H⋯O inter­actions. The absolute configuration was assigned on the basis of literature data. International Union of Crystallography 2010-05-15 /pmc/articles/PMC2979606/ /pubmed/21579436 http://dx.doi.org/10.1107/S1600536810016582 Text en © Sarigaputi 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
Sarigaputi, Chanin
Teerawatananond, Thapong
Pengpreecha, Somchai
Muangsin, Nongnuj
Pudhom, Khanitha
Xyloccensin E
title Xyloccensin E
title_full Xyloccensin E
title_fullStr Xyloccensin E
title_full_unstemmed Xyloccensin E
title_short Xyloccensin E
title_sort xyloccensin e
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2979606/
https://www.ncbi.nlm.nih.gov/pubmed/21579436
http://dx.doi.org/10.1107/S1600536810016582
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AT pudhomkhanitha xyloccensine