Zearalenone
Title: Zearalenone
CAS Registry Number: 17924-92-4
CAS Name: (3S,11E)-3,4,5,6,9,10-Hexahydro-14,16-dihydroxy-3-methyl-1H-2-benzoxacyclotetradecin-1,7(8H)-dione
Additional Names: 6-(10-hydroxy-6-oxo-trans-1-undecenyl)-b-resorcylic acid lactone; Compd F-2; FES
Molecular Formula: C18H22O5
Molecular Weight: 318.36
Percent Composition: C 67.91%, H 6.97%, O 25.13%
Literature References: Estrogenic mycotoxin produced by Fusarium fungi commonly found in grains. One of a group of compounds known as resorcylic acid lactones. Isoln from the mycelia of Gibberella zeae (Fusarium graminearum): M. Stob et al., Nature 196, 1318 (1962); F. N. Andrews, M. Stob, US 3196019 (1965 to Purdue Res. Found.). Structure: W. H. Urry et al., Tetrahedron Lett. 1966, 3109. Synthesis of dl-form: D. Taub et al., Chem. Commun. 1967, 225; NL 6812148; N. N. Girotra, N. L. Wendler, US 3551455 (1968, 1970 both to Merck & Co.); Vlattas et al., J. Org. Chem. 33, 4176 (1968); T. Takahashi et al., Tetrahedron Lett. 22, 1363 (1981). Total synthesis and abs config: D. Taub et al., Tetrahedron 24, 2443 (1968). Physicochemical data: A. E. Pohland et al., Pure Appl. Chem. 54, 2219 (1982). Natural occurrence in agricultural products: T. Tanaka et al., J. Agric. Food Chem. 36, 979 (1988). GC determn in cereals: K. Schwadorf, H.-M. Müller, J. Chromatogr. 595, 259 (1992).
Properties: Crystals, mp 164-165°. [a]25546 -170.5° (c = 1.0 in CH3OH). uv max (CH3OH): 236, 274, 316 nm (e 29700; 13909; 6020). Sol in aq alkali, ether, benzene, alcohols. Practically insol in water.
Melting point: mp 164-165°
Optical Rotation: [a]25546 -170.5° (c = 1.0 in CH3OH)
Absorption maximum: uv max (CH3OH): 236, 274, 316 nm (e 29700; 13909; 6020)
 
Derivative Type: dl-Form
Properties: Crystals, mp 187-189°.
Melting point: mp 187-189°

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