[1R-(1 alpha,2 alpha,4 alpha,5 beta,6 alpha,7 alpha)]-4-Benzoyloxymethyl-5,6-dihydroxy-3,8-ioxatricyclo[5.1.0.0(2,4)]octan-5-yl acetate (3-deacetylcrotepoxide) from Kaempferia rotunda Val.
The title compound, C16H16O7, 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 CH3CO2- and HO- substituents occupy eq...
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International Union of Crystallography
2010
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author | Mohd. Sirat, Hasnah Feng, Y. S. Awang, Khalijah Ng, Seik Weng |
author_facet | Mohd. Sirat, Hasnah Feng, Y. S. Awang, Khalijah Ng, Seik Weng |
author_sort | Mohd. Sirat, Hasnah |
collection | ePrints |
description | The title compound, C16H16O7, 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 CH3CO2- and HO- substituents occupy equatorial positions. However, the bond angles at the ring carbon connected to the C6H5CO2CH2- 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-HO hydrogen bonds. |
first_indexed | 2024-03-05T18:41:44Z |
format | Article |
id | utm.eprints-27080 |
institution | Universiti Teknologi Malaysia - ePrints |
last_indexed | 2024-03-05T18:41:44Z |
publishDate | 2010 |
publisher | International Union of Crystallography |
record_format | dspace |
spelling | utm.eprints-270802017-05-05T02:21:41Z http://eprints.utm.my/27080/ [1R-(1 alpha,2 alpha,4 alpha,5 beta,6 alpha,7 alpha)]-4-Benzoyloxymethyl-5,6-dihydroxy-3,8-ioxatricyclo[5.1.0.0(2,4)]octan-5-yl acetate (3-deacetylcrotepoxide) from Kaempferia rotunda Val. Mohd. Sirat, Hasnah Feng, Y. S. Awang, Khalijah Ng, Seik Weng Q Science The title compound, C16H16O7, 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 CH3CO2- and HO- substituents occupy equatorial positions. However, the bond angles at the ring carbon connected to the C6H5CO2CH2- 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-HO hydrogen bonds. International Union of Crystallography 2010 Article PeerReviewed Mohd. Sirat, Hasnah and Feng, Y. S. and Awang, Khalijah and Ng, Seik Weng (2010) [1R-(1 alpha,2 alpha,4 alpha,5 beta,6 alpha,7 alpha)]-4-Benzoyloxymethyl-5,6-dihydroxy-3,8-ioxatricyclo[5.1.0.0(2,4)]octan-5-yl acetate (3-deacetylcrotepoxide) from Kaempferia rotunda Val. Acta Crystallographica Section E-Structure Reports Online, 66 . O2945-U1324. ISSN 1600-5368 http://dx.doi.org/10.1107/S1600536810042686 DOI:10.1107/S1600536810042686 |
spellingShingle | Q Science Mohd. Sirat, Hasnah Feng, Y. S. Awang, Khalijah Ng, Seik Weng [1R-(1 alpha,2 alpha,4 alpha,5 beta,6 alpha,7 alpha)]-4-Benzoyloxymethyl-5,6-dihydroxy-3,8-ioxatricyclo[5.1.0.0(2,4)]octan-5-yl acetate (3-deacetylcrotepoxide) from Kaempferia rotunda Val. |
title | [1R-(1 alpha,2 alpha,4 alpha,5 beta,6 alpha,7 alpha)]-4-Benzoyloxymethyl-5,6-dihydroxy-3,8-ioxatricyclo[5.1.0.0(2,4)]octan-5-yl acetate (3-deacetylcrotepoxide) from Kaempferia rotunda Val. |
title_full | [1R-(1 alpha,2 alpha,4 alpha,5 beta,6 alpha,7 alpha)]-4-Benzoyloxymethyl-5,6-dihydroxy-3,8-ioxatricyclo[5.1.0.0(2,4)]octan-5-yl acetate (3-deacetylcrotepoxide) from Kaempferia rotunda Val. |
title_fullStr | [1R-(1 alpha,2 alpha,4 alpha,5 beta,6 alpha,7 alpha)]-4-Benzoyloxymethyl-5,6-dihydroxy-3,8-ioxatricyclo[5.1.0.0(2,4)]octan-5-yl acetate (3-deacetylcrotepoxide) from Kaempferia rotunda Val. |
title_full_unstemmed | [1R-(1 alpha,2 alpha,4 alpha,5 beta,6 alpha,7 alpha)]-4-Benzoyloxymethyl-5,6-dihydroxy-3,8-ioxatricyclo[5.1.0.0(2,4)]octan-5-yl acetate (3-deacetylcrotepoxide) from Kaempferia rotunda Val. |
title_short | [1R-(1 alpha,2 alpha,4 alpha,5 beta,6 alpha,7 alpha)]-4-Benzoyloxymethyl-5,6-dihydroxy-3,8-ioxatricyclo[5.1.0.0(2,4)]octan-5-yl acetate (3-deacetylcrotepoxide) from Kaempferia rotunda Val. |
title_sort | 1r 1 alpha 2 alpha 4 alpha 5 beta 6 alpha 7 alpha 4 benzoyloxymethyl 5 6 dihydroxy 3 8 ioxatricyclo 5 1 0 0 2 4 octan 5 yl acetate 3 deacetylcrotepoxide from kaempferia rotunda val |
topic | Q Science |
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