Research Article: (3S)-14,16-Dihy­droxy-3-methyl-3,4,5,6,9,10,11,12-octa­hydro-1H-2-benzoxacyclo­tetra­decine-1,7(8H)-dione (zearalanone) monohydrate

Date Published: May 01, 2012

Publisher: International Union of Crystallography

Author(s): Sarah Drzymala, Werner Kraus, Franziska Emmerling, Matthias Koch.


The absolute configuration of the title compound, C18H24O5·H2O, was not been determined by anomalous-dispersion effects, but has been assigned by reference to an unchanging chiral centre in the synthetic procedure. Intra­molecular O—H⋯O hydrogen bonds stabilize the mol­ecular conformation. In the crystal, O—H⋯O hydrogen bonds link the main mol­ecules and the water mol­ecules, forming an infinite three-dimensional network.

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For the preparation of zearalanone from natural zearalenone, see: Urry et al. (1966 ▶). For the crystal structures of zearalenone and its derivatives, see: Panneerselvam et al. (1996 ▶); Gelo-Pujić et al. (1994 ▶); Zhao et al. (2008 ▶). For the estrogenic and anabolic effects of zearalenone and its derivatives, see: Mirocha et al. (1968 ▶). For the exploitation of zearalanone as an inter­nal standard, see: Berthiller et al. (2005 ▶); Maragou et al. (2008 ▶); Ren et al. (2007 ▶); Shin et al. (2009 ▶).