The identification and crystal structure of a hydropericardium-producing factor: 1,2,3,7,8,9-hexachlorodibenzo-p-dioxin

The three-dimensional structure of 3,3′,4,4′-tetrachlorobiphenyl, a dioxin-like polychlorinated biphenyl (PCB)

“…This compound is a metabolite of PCB 77 (Doi et al, 2006;Koga et al, 1989) and has a strong affinity to both human estrogen sulfotransferase (Shevtsov et al, 2003) and thyroxine (McKinney et al, 1987). 3,3′,5,5′-tetrachloro-4,4′-dihydroxybiphenyl, like chlorinated dioxins Cantrell et al, 1989;Cantrell et al, 1969;Koester et al, 1988), is essentially coplanar in the solid state, and thus adopts a conformation that is significantly different from that of PCB 77. The tendency of this dihydroxylated PCB derivative to adopt a more planar conformation in the solid state is due to the stabilizing intermolecular interactions resulting, in part, from a stacking arrangement of the benzene rings (McKinney and Singh, 1988).…”

Hexafluorophosphate Salts of Cyclopentadienyliron(II) Complexes of Dibenzodioxin and 1-Methyldibenzodioxin

“…Displacement ellipsoids are plotted at the 50% probability level. 2,3,7,8,9-hexachlorodibenzodioxin [175.7°;Cantrell, Webb & Mabis, 1969], while dibenzodioxin (Senma, Taira, Taga & Osaki, 1973;Singh & McKinney, 1978), 2,7-dichlorodibenzodioxin , 2,3,7,8-tetrachlorodibenzodioxin (Boer, van Remoortere, North & Neuman, 1972), octachlorodibenzodioxin and octafluorodibenzodioxin (Rainville, Zingaro & Meyers, 1980) are planar. The above data seem to indicate that FeCp complexation and the introduction of substituents into the dibenzodioxin ring may result in deviation of the molecule from planarity.…”

Metabolism of dibenzo[1,4]dioxan by a Pseudomonas species

“…Interest in chlorinated dibenzo [1,4]dioxans arose with the identification by X-ray diffraction of 1,2,3,7,8,9-hexachlorodibenzo-[1,4]dioxan as the 'chick oedema factor' that caused the deaths of millions of broiler chickens in 1957 (Cantrell et al, 1969). It is now known that conditions utilized in the synthesis of certain chlorinated fungicides and herbicides, such as pentachlorophenol, 2,4,5-trichlorophenol and 2,4,5-trichlorophenoxyacetic acid can result in the formation of chlorinated dibenzo [1 ,4]dioxans.…”