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United States Department of Agriculture

Agricultural Research Service

Title: The Inclusion Complex of (-)-Gossypol with 2,4-Pentanedione

Authors
item Dowd, Michael
item Stevens, Edwin - UNIV OF NEW ORLEAN

Submitted to: Meeting Abstract
Publication Type: Abstract Only
Publication Acceptance Date: March 11, 2004
Publication Date: May 9, 2004
Citation: Dowd, M.K., Stevens, E.D. 2004. The inclusion complex of (-)-gossypol with 2,4-pentanedione (abstract}. American Oil Chemists' Society. p.123

Technical Abstract: An inclusion complex was formed between (-)-gossypol and 2,4-pentanedione by vapor diffusion of petroleum ether into a solution of (-)-gossypol and 2,4-pentanedione. The solvate contains a one-to-two molar ratio of gossypol and 2,4-pentanedione. The structure is tetragonal with a P41212 space group and has unit cell dimensions of a = b = 10.9966(7) A and c = 60.213(4) A. Both solvent molecules are in the enol-keto form. Two distinct solvent sites are formed within the structure. The first solvent site, containing two symmetry related solvent molecules, is formed between pairs of gossypol naphthalene rings. Each solvent molecule is hydrogen bonded to one of the surrounding gossypol molecules. The four molecules form a wedged-shaped assembly that is repeated throughout the cell. The point of each "wedge" fits into the hollow of the next "wedge" to form a stacked column, with adjacent columns aligned parallel to form layers. Neighboring layers are shifted by 90 degrees to account for the four-fold symmetric of the space group. The second solvent site is located in isolated pockets that form between the layers. These solvent molecules are hydrogen bonded to gossypol molecules from the adjacent layers. This compound is the first example of a gossypol tetragonal crystal form and is the first example of a chiral gossypol solvate that does not lose solvent when removed from the mother liquor.

Last Modified: 10/23/2014
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