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United States Department of Agriculture

Agricultural Research Service

Title: The Gossypol-Cyclododecanone (1/2) Inclusion Complex

Authors
item Dowd, Michael
item Stevens, Edwin - DEPT.CHEM.,UNO,N.O.

Submitted to: Acta Crystallographica Section C: Crystal Structure Communications
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: May 19, 2003
Publication Date: June 30, 2003
Citation: Dowd, M.K., Stevens, E.D. 2003. The gossypol-cyclododecanone (1/2) inclusion complex. Acta Crystallographica Section C: Crystal Structure Communications. 59(7):0397-0399

Interpretive Summary: Low temperature x-ray diffraction was used to study the structure of a new form of gossypol, a natural product of the cotton plant. The x-ray diffraction patterns indicated that each gossypol molecule was complexed with two molecules of cyclododecanone. The results will be of interest to scientists working to develop products based on gossypol's unusual ability to form inclusion complexes.

Technical Abstract: Gossypol and cyclododecanone crystallize at room temperature as an inclusion complex in a 1-to-2 molar ratio. Although gossypol is known to form complexes with many small molecular weight organic compounds, this complex is unusual in that there is limited intermolecular hydrogen bonding within the structure. Each cyclododecanone molecule accepts a hydrogen bond from a gossypol molecular, but there are no gossypol-to-gossypol hydrogen bond interactions. The gossypol molecules interact via van der Waals effects to form a lattice structure, and the cyclodecanone molecules lie in channels formed within this lattice. In terms of the number of non-hydrogen guest atoms, this is the largest gossypol inclusion complex reported to date.

Last Modified: 11/20/2014
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