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Title: 6,6´-Dimethoxygossypolone

item ZELAYA, CARLOS - University Of New Orleans
item STEVENS, EDWIN - University Of New Orleans
item Dowd, Michael

Submitted to: Acta Crystallographica Section C: Crystal Structure Communications
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 9/13/2010
Publication Date: 9/24/2010
Citation: Zelaya, C.A., Stevens, E.D., Dowd, M.K. 2010. 6,6´-Dimethoxygossypolone. Acta Crystallographica Section C: Crystal Structure Communications. C66:o517-o520.

Interpretive Summary: Low temperature x-ray diffraction was used to study the structure of 6,6´-dimethoxy-gossypolone, which is synthesized by mild oxidation from 6,6´-dimethoxygossypol, a natural product of some cotton plants. The x-ray diffraction data indicate that the rings of this compound exhibit some unusual conformations. The results will be of interest to scientists working to develop products based on gossypol unusual ability to form inclusion complexes.

Technical Abstract: 6,6'-Dimethoxygossypolone [7,7'-dihydroxy-5,5'-diisopropyl-6,6'-dimethoxy-3,3'-dimethyl-(2,2'-binaphtho-1,4-quinone)-8,8'-dicarboxaldehyde], C32-H30-O10, has monoclinic (P21/c) symmetry. There are two molecules within the asymmetric unit. Of the four independent quinoid rings, three display flattened boat conformations and one displays a flattened chair/half-chair conformation. The angle between the planes of the bridged naphthoquinone rings is fairly acute, with values of 68 and 69°. The structure has intramolecular but no intermolecular O—H hydrogen bonding.