Research Article: (3S,11Z)-14,16-Dihy­droxy-3-methyl-3,4,5,6,9,10-hexa­hydro-1H-2-benz­oxacyclo­tetra­decine-1,7(8H)-dione (cis-zearalenone): a redetermination

Date Published: March 01, 2012

Publisher: International Union of Crystallography

Author(s): Robert Köppen, Juliane Riedel, Franziska Emmerling, Matthias Koch.


The title compound, also known as cis-zearalenone (cis-ZEN), C18H22O5, has already been reported elsewhere [Griffin et al. (1981 ▶). ACA Ser.29, 35], but no atomic coordinates are publicly available. The mol­ecule is of inter­est with respect to its toxicity. In the crystal, intra­molecular O—H⋯O hydrogen bonds stabilize the mol­ecular conformation, while inter­molecular O—H⋯O hydrogen bonds link the mol­ecules to form infinite chains along the [110] and [1-10] directions. The absolute configuration has been assigned by reference to an unchanging chiral centre in the synthetic procedure.

Partial Text

For the crystal structures of trans-zearalenone (trans-ZEN) and zearalenol, see: Gelo-Pujić et al. (1994 ▶) and Zhao et al. (2008 ▶). For more detailed information about trans-ZEN and its metabolites, see: Urry et al. (1966 ▶) and Zinedine et al. (2007 ▶).