Abstract
The title compound, C34H38O8 (systematic name: 5,5'-diisopropyl-2,2',3,3'-tetra-meth-oxy-7,7'-dimethyl-2H,2'H-8,8'-bi-[naphtho-[1,8-bc]furan]-4,4'-diol), has been obtained from a gossypol solution in a mixture of dimethyl sulfate and methanol. The mol-ecule is situated on a twofold rotation axis, so the asymmetric unit contains one half-mol-ecule. In the mol-ecule, the hy-droxy groups are involved in intra-molecular O-H⋯O hydrogen bonds, and the two naphthyl fragments are inclined each to other by 83.8 (1)°. In the crystal, weak C-H⋯O and C-H⋯π inter-actions consolidate the packing, which exhibits channels with an approximate diameter of 6 Å extending along the c-axis direction. These channels are filled with highly disordered solvent mol-ecules, so their estimated scattering contribution was subtracted from the observed diffraction data using the SQUEEZE option in PLATON [Spek, A. L. (2015). Acta Cryst. C71, 9-18].
Highlights
The title compound, C34H38O8, has been obtained from a gossypol solution in a mixture of dimethyl sulfate and methanol
There are some reports that gossypol exists in a pure lactol form (Reyes et al, 1986) or as a dynamic equilibrium mixture of the aldehyde and lactol forms in some highly polar solvents (Kamaev et al, 1979)
In the structure described here, the title compound exists in the lactol form
Summary
Gossypol [systematic name: 2,20 -bis(8-formyl-1,6,7-trihydroxyl-5-isopropyl-3-methylnaphthalene)] is an unique terpenoid found in Gossypium (cotton) and related species. The compound has a wide range of biological actions, including anti-HIV, anticancer, and antifertility effects (Liang et al, 1995; Dorsett et al, 1975; Coutinho, 2002; Royer et al, 1995). Gossypol is a surprisingly versatile host compound that forms inclusion complexes with a great variety of organic substances such as ketones, ethers, esters, organic and mineral acids, water, various benzyl compounds and chlorinated and brominated compounds. Many derivatives have been reported, including ethers, acetates and Schiff bases with aldehydes (Talipov et al., 2004; 2009; Tilyabaev et al, 2009; Kenar, 2006). As first reported by Morris & Adams (1937), treatment with an alkali of a gossypol solution in a mixture of dimethyl sulfate and methanol, yields a white gossypol tetramethyl ether, the title compound. Symmetry codes: (i) x; y; z þ 2; (ii) x; y; z þ 12
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