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[1R-(1 alpha,2 alpha,4 alpha,5 beta,6 alpha,7 alpha)]-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, 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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Main Authors: Sirat, H.M., Feng, Y.S., Awang, K., Ng, S.W.
Format: Article
Published: International Union of Crystallography 2010
Subjects:
Q Science (General)
Online Access:http://eprints.um.edu.my/12041/
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spelling my.um.eprints.120412019-01-30T09:14:45Z http://eprints.um.edu.my/12041/ [1R-(1 alpha,2 alpha,4 alpha,5 beta,6 alpha,7 alpha)]-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, H.M. Feng, Y.S. Awang, K. Ng, S.W. Q Science (General) 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-H center dot center dot center dot O hydrogen bonds. International Union of Crystallography 2010 Article PeerReviewed Sirat, H.M. and Feng, Y.S. and Awang, K. and Ng, S.W. (2010) [1R-(1 alpha,2 alpha,4 alpha,5 beta,6 alpha,7 alpha)]-4-Benzoyloxymethyl-5,6-dihydroxy-3,8-dioxatricyclo[5.1.0.0(2,4 )]octan-5-yl acetate (3-deacetylcrotepoxide) from Kaempferia rotunda Val. Acta Crystallographica Section E: Structure Reports Online, 66 (11). O2945-U1324. ISSN 1600-5368
institution Universiti Malaya
building UM Library
collection Institutional Repository
continent Asia
country Malaysia
content_provider Universiti Malaya
content_source UM Research Repository
url_provider http://eprints.um.edu.my/
topic Q Science (General)
spellingShingle Q Science (General)
Sirat, H.M.
Feng, Y.S.
Awang, K.
Ng, S.W.
[1R-(1 alpha,2 alpha,4 alpha,5 beta,6 alpha,7 alpha)]-4-Benzoyloxymethyl-5,6-dihydroxy-3,8-dioxatricyclo[5.1.0.0(2,4 )]octan-5-yl acetate (3-deacetylcrotepoxide) from Kaempferia rotunda Val
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-H center dot center dot center dot O hydrogen bonds.
format Article
author Sirat, H.M.
Feng, Y.S.
Awang, K.
Ng, S.W.
author_facet Sirat, H.M.
Feng, Y.S.
Awang, K.
Ng, S.W.
author_sort Sirat, H.M.
title [1R-(1 alpha,2 alpha,4 alpha,5 beta,6 alpha,7 alpha)]-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-(1 alpha,2 alpha,4 alpha,5 beta,6 alpha,7 alpha)]-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-(1 alpha,2 alpha,4 alpha,5 beta,6 alpha,7 alpha)]-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-(1 alpha,2 alpha,4 alpha,5 beta,6 alpha,7 alpha)]-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-(1 alpha,2 alpha,4 alpha,5 beta,6 alpha,7 alpha)]-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-(1 alpha,2 alpha,4 alpha,5 beta,6 alpha,7 alpha)]-4-benzoyloxymethyl-5,6-dihydroxy-3,8-dioxatricyclo[5.1.0.0(2,4 )]octan-5-yl acetate (3-deacetylcrotepoxide) from kaempferia rotunda val
publisher International Union of Crystallography
publishDate 2010
url http://eprints.um.edu.my/12041/
_version_ 1643689205256159232
score 13.18916

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