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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...

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Detalles Bibliográficos
Autores principales: Sirat, Hasnah Mohd, Feng, Yau Sui, Awang, Khalijah, Ng, Seik Weng
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2010
Materias:
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
Descripción
Sumario: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.