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United States Department of Agriculture

Agricultural Research Service

Research Project: Value-Added Products from Cottonseed

Location: Commodity Utilization Research

Title: Di(phenylpropylamino)gossypol: a derivative of the dimeric natural product gossypol

Authors
item Zelaya, Carlos -
item Stevens, Edwin -
item Dowd, Michael

Submitted to: Acta Crystallographica Section C: Crystal Structure Communications
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: March 5, 2013
Publication Date: April 1, 2013
Citation: Zelaya, C.A., Stevens, E.D., Dowd, M.K. 2013. Di(phenylpropylamino)gossypol: a derivative of the dimeric natural product gossypol. Acta Crystallographica Section C: Crystal Structure Communications. 69(4):439-443.

Interpretive Summary: Di(phenylpropylamino)gossypol was synthesized by mixing 3-phenylpropylamine and gossypol in ethanol and heating to 50 °C for a few hours. Room and low temperature -ray diffraction was used to study the structure of the derivative. The diffraction data indicate that the compound crystallizes without solvent, which is unusual for many gossypol compounds. The results will be of interest to scientists working to develop products based on gossypol unusual ability to form inclusion complexes with many types of molecules.

Technical Abstract: Di(phenylpropylamino)gossypol [2,2'-bis(1,6-dihydroxy,-5-isopropyl,-8-methineaminopropylbenzene-3-methyl)-naphthylene-7-one, C48H52N2O6] is formed by reaction of the dimeric natural product gossypol with 3-phenyl-1-propylamine. When crystallized from diethyl ether, the compound has monoclinic (P21/c) symmetry with a single molecule in the asymmetric unit. The two 3-phenylpropyl moieties have different conformations. One of these groups is considerably disordered at room temperature but is less disordered at 120 K. The enantiomeric molecules form centrosymmetric dimers that align to form columns. Hydrophobic interactions between neighboring naphthalene rings and intermolecular hydrogen bonds support the dimers and columns. The compound crystallizes without the inclusion of solvent, which appears to occur because of the size and flexibility of its phenylpropyl pendent groups.

Last Modified: 8/21/2014
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