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[1R-(1α,2α,4α,5β,6α,7α)]-4-Benzoyloxymethyl-5,6-dihydroxy-3,8-dioxatricyclo[5.1.0.0(2,4)]octan-5-yl acetate (3-deacetylcrotepoxide) from Kaempferia rotunda Val.
The title compound, C(16)H(16)O(7), isolated from Kaempferia rotunda rhizomes, features a six-membered cyclohexane ring that adopts a twisted-boat conformation owing to the presence of two adjacent epoxide attachments that lock in four of the six axial positions. The CH(3)CO(2)– and HO– substituent...
| Autores principales: | , , , |
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| Formato: | Texto |
| Lenguaje: | English |
| Publicado: |
International Union of Crystallography
2010
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| Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3009124/ https://www.ncbi.nlm.nih.gov/pubmed/21589115 http://dx.doi.org/10.1107/S1600536810042686 |
| _version_ | 1782194612507508736 |
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| author | Sirat, Hasnah Mohd Feng, Yau Sui Awang, Khalijah Ng, Seik Weng |
| author_facet | Sirat, Hasnah Mohd Feng, Yau Sui Awang, Khalijah Ng, Seik Weng |
| author_sort | Sirat, Hasnah Mohd |
| collection | PubMed |
| description | The title compound, C(16)H(16)O(7), isolated from Kaempferia rotunda rhizomes, features a six-membered cyclohexane ring that adopts a twisted-boat conformation owing to the presence of two adjacent epoxide attachments that lock in four of the six axial positions. The CH(3)CO(2)– and HO– substituents occupy equatorial positions. However, the bond angles at the ring carbon connected to the C(6)H(5)CO(2)CH(2)– substituent deviate signifcantly from the idealized tetrahedral angles as the carbon atom is part of an epoxide ring. In the crystal, the molecules are linked into chains by O—H⋯O hydrogen bonds. |
| format | Text |
| id | pubmed-3009124 |
| institution | National Center for Biotechnology Information |
| language | English |
| publishDate | 2010 |
| publisher | International Union of Crystallography |
| record_format | MEDLINE/PubMed |
| spelling | pubmed-30091242010-12-30 [1R-(1α,2α,4α,5β,6α,7α)]-4-Benzoyloxymethyl-5,6-dihydroxy-3,8-dioxatricyclo[5.1.0.0(2,4)]octan-5-yl acetate (3-deacetylcrotepoxide) from Kaempferia rotunda Val. Sirat, Hasnah Mohd Feng, Yau Sui Awang, Khalijah Ng, Seik Weng Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(16)H(16)O(7), isolated from Kaempferia rotunda rhizomes, features a six-membered cyclohexane ring that adopts a twisted-boat conformation owing to the presence of two adjacent epoxide attachments that lock in four of the six axial positions. The CH(3)CO(2)– and HO– substituents occupy equatorial positions. However, the bond angles at the ring carbon connected to the C(6)H(5)CO(2)CH(2)– substituent deviate signifcantly from the idealized tetrahedral angles as the carbon atom is part of an epoxide ring. In the crystal, the molecules are linked into chains by O—H⋯O hydrogen bonds. International Union of Crystallography 2010-10-30 /pmc/articles/PMC3009124/ /pubmed/21589115 http://dx.doi.org/10.1107/S1600536810042686 Text en © Sirat 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 Sirat, Hasnah Mohd Feng, Yau Sui Awang, Khalijah Ng, Seik Weng [1R-(1α,2α,4α,5β,6α,7α)]-4-Benzoyloxymethyl-5,6-dihydroxy-3,8-dioxatricyclo[5.1.0.0(2,4)]octan-5-yl acetate (3-deacetylcrotepoxide) from Kaempferia rotunda Val. |
| title | [1R-(1α,2α,4α,5β,6α,7α)]-4-Benzoyloxymethyl-5,6-dihydroxy-3,8-dioxatricyclo[5.1.0.0(2,4)]octan-5-yl acetate (3-deacetylcrotepoxide) from Kaempferia rotunda Val. |
| title_full | [1R-(1α,2α,4α,5β,6α,7α)]-4-Benzoyloxymethyl-5,6-dihydroxy-3,8-dioxatricyclo[5.1.0.0(2,4)]octan-5-yl acetate (3-deacetylcrotepoxide) from Kaempferia rotunda Val. |
| title_fullStr | [1R-(1α,2α,4α,5β,6α,7α)]-4-Benzoyloxymethyl-5,6-dihydroxy-3,8-dioxatricyclo[5.1.0.0(2,4)]octan-5-yl acetate (3-deacetylcrotepoxide) from Kaempferia rotunda Val. |
| title_full_unstemmed | [1R-(1α,2α,4α,5β,6α,7α)]-4-Benzoyloxymethyl-5,6-dihydroxy-3,8-dioxatricyclo[5.1.0.0(2,4)]octan-5-yl acetate (3-deacetylcrotepoxide) from Kaempferia rotunda Val. |
| title_short | [1R-(1α,2α,4α,5β,6α,7α)]-4-Benzoyloxymethyl-5,6-dihydroxy-3,8-dioxatricyclo[5.1.0.0(2,4)]octan-5-yl acetate (3-deacetylcrotepoxide) from Kaempferia rotunda Val. |
| title_sort | [1r-(1α,2α,4α,5β,6α,7α)]-4-benzoyloxymethyl-5,6-dihydroxy-3,8-dioxatricyclo[5.1.0.0(2,4)]octan-5-yl acetate (3-deacetylcrotepoxide) from kaempferia rotunda val. |
| topic | Organic Papers |
| url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3009124/ https://www.ncbi.nlm.nih.gov/pubmed/21589115 http://dx.doi.org/10.1107/S1600536810042686 |
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