[1R-(1α,2α,4α,5β,6α,7α)]-4-Benzoyl-oxymethyl-5,6-dihy-droxy-3,8-dioxa-tricyclo-[5.1.0.0]octan-5-yl acetate (3-deacetyl-crotepoxide) from Kaempferia rotunda Val.

ABSTRACT: The title compound, C(16)H(16)O(7), isolated from Kaempferia rotunda rhizomes, features a six-membered cyclo-hexane 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 tetra-hedral 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.

SUBMITTER: Sirat HM 

PROVIDER: S-EPMC3009124 | biostudies-literature | 2010 Oct

REPOSITORIES: biostudies-literature