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Redetermination and absolute configuration of 7α-hydroxyroyleanone
The title compound [systematic name: 7α,12-dihydroxy-8,12-abietadiene,11,14-dione or (4bS,8aS,10R)-3,10-dihydroxy-2-isopropyl-4b,8,8-trimethyl-1,4,4b,5,6,7,8,8a,9,10-decahydrophenanthrene-1,4-dione], C(20)H(28)O(4), is an abietane diterpenoid, which was isolated from the roots of Premna obtusif...
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Formato: | Texto |
Lenguaje: | English |
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International Union of Crystallography
2010
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3006754/ https://www.ncbi.nlm.nih.gov/pubmed/21587809 http://dx.doi.org/10.1107/S1600536810020544 |
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author | Razak, Ibrahim Abdul Salae, Abdul Wahab Chantrapromma, Suchada Karalai, Chatchanok Fun, Hoong-Kun |
author_facet | Razak, Ibrahim Abdul Salae, Abdul Wahab Chantrapromma, Suchada Karalai, Chatchanok Fun, Hoong-Kun |
author_sort | Razak, Ibrahim Abdul |
collection | PubMed |
description | The title compound [systematic name: 7α,12-dihydroxy-8,12-abietadiene,11,14-dione or (4bS,8aS,10R)-3,10-dihydroxy-2-isopropyl-4b,8,8-trimethyl-1,4,4b,5,6,7,8,8a,9,10-decahydrophenanthrene-1,4-dione], C(20)H(28)O(4), is an abietane diterpenoid, which was isolated from the roots of Premna obtusifolia (Verbenaceae). Its crystal structure has been reported previously [Chen et al. (2000 ▶). Jiegou Huaxue, 19, 122–125], but the absolute configuration could not be determined using data collected with Mo radiation. This redetermination using Cu radiation shows the the absolute configurations of the stereogenic centres at positions 4b, 8a and 10 to be S, S and R, respectively. Two intramolecular O—H⋯O hydrogen bonds [one generating an S(5) ring and one generating an S(6) ring] and a number of short C—H⋯O contacts occur. In the crystal, molecules are linked into infinite chains propagating in [100] by O—H⋯O hydrogen bonds and weak C—H⋯O interactions. |
format | Text |
id | pubmed-3006754 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2010 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-30067542010-12-30 Redetermination and absolute configuration of 7α-hydroxyroyleanone Razak, Ibrahim Abdul Salae, Abdul Wahab Chantrapromma, Suchada Karalai, Chatchanok Fun, Hoong-Kun Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound [systematic name: 7α,12-dihydroxy-8,12-abietadiene,11,14-dione or (4bS,8aS,10R)-3,10-dihydroxy-2-isopropyl-4b,8,8-trimethyl-1,4,4b,5,6,7,8,8a,9,10-decahydrophenanthrene-1,4-dione], C(20)H(28)O(4), is an abietane diterpenoid, which was isolated from the roots of Premna obtusifolia (Verbenaceae). Its crystal structure has been reported previously [Chen et al. (2000 ▶). Jiegou Huaxue, 19, 122–125], but the absolute configuration could not be determined using data collected with Mo radiation. This redetermination using Cu radiation shows the the absolute configurations of the stereogenic centres at positions 4b, 8a and 10 to be S, S and R, respectively. Two intramolecular O—H⋯O hydrogen bonds [one generating an S(5) ring and one generating an S(6) ring] and a number of short C—H⋯O contacts occur. In the crystal, molecules are linked into infinite chains propagating in [100] by O—H⋯O hydrogen bonds and weak C—H⋯O interactions. International Union of Crystallography 2010-06-05 /pmc/articles/PMC3006754/ /pubmed/21587809 http://dx.doi.org/10.1107/S1600536810020544 Text en © Razak 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 Razak, Ibrahim Abdul Salae, Abdul Wahab Chantrapromma, Suchada Karalai, Chatchanok Fun, Hoong-Kun Redetermination and absolute configuration of 7α-hydroxyroyleanone |
title | Redetermination and absolute configuration of 7α-hydroxyroyleanone |
title_full | Redetermination and absolute configuration of 7α-hydroxyroyleanone |
title_fullStr | Redetermination and absolute configuration of 7α-hydroxyroyleanone |
title_full_unstemmed | Redetermination and absolute configuration of 7α-hydroxyroyleanone |
title_short | Redetermination and absolute configuration of 7α-hydroxyroyleanone |
title_sort | redetermination and absolute configuration of 7α-hydroxyroyleanone |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3006754/ https://www.ncbi.nlm.nih.gov/pubmed/21587809 http://dx.doi.org/10.1107/S1600536810020544 |
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