10121. Zeranol

Nomenclature

CAS number: 26538-44-3
(3S,7R)-3,4,5,6,7,8,9,10,11,12-Decahydro-7,14,16-trihydroxy-3-methyl-1H-2-benzoxacyclotetradecin-1-one; 6-(6,10-dihydroxyundecyl)-β-resorcylic acid μ-lactone; α-zearalanol; MK-188; P-1496; Ralgro (Mallinckrodt Vet.); Ralabol (Mallinckrodt Vet.); Ralone (Mallinckrodt Vet.).
C18H26O5; mol wt 322.40.
C 67.06%, H 8.13%, O 24.81%.

Description and references

Animal growth promotant prepd from zearalenone, q.v.: E. B. Hodge et al., US 3239345 (1966 to Commercial Solvents). Stereoselective prepn and abs config: G. Snatzke et al., Helv. Chim. Acta 69, 734 (1986). TLC determn in plasma and tissues: M. B. Medina, N. Nagdy, J. Chromatogr. 614, 315 (1993). Growth regulating and repartitioning effects in cattle: P. G. Lemieux et al., J. Anim. Sci. 68, 1702 (1990). Review: R. S. Baldwin et al., Regul. Toxicol. Pharmacol. 3, 9-25 (1983).

Chemical structure

Properties

Crystals from isopropanol/water, mp 182-183°; [α]D +46.3° (c = 1.0 in methanol). LD50 in mice (mg/kg): 4400 i.p.; >40000 orally (Baldwin).

Therapeutic Category (Veterinary)

Anabolic.