Zeranol

Chemical properties

Off-White to Tan

Originator

Ralone,I.C.I. ,Italy ,1975

The Uses of Zeranol

α-Zearalanol is a minor analogue of the zearalenone family of resorcinyl macrocyclic lactones, produced by several species of Fusarium. Like the other zearalenones, α-zearalanol exhibits estrogenic activity in animals. The potency of α-zearalanol, generically known as zeranol, lead to its commercial development as a growth promotant in livestock.

The Uses of Zeranol

Animal growth promotant. Anabolic. Controlled substance

What are the applications of Application

α-Zearalanol is an estrogen receptor agonist

Definition

ChEBI: Alpha-Zearalanol is a macrolide.

Manufacturing Process

A spore sand culture containing Gibberella zeae (Gordon) NRR L-2830 was aseptically placed in a sterile tube containing 15 ml of Czapek's-Dox solution and a small amount of agar. This medium was then incubated for about 168 hours at approximately 25°C. At the end of the incubation period, the medium was washed with 5 ml of sterile deionized water and transferred to a sterile tube containing 45 ml of Czapek's-Dox solution. The contents of the tube were then incubated for about 96 hours at about 25°C after which the material was available for use in inoculation of a fermentation medium.
To a 2-liter flask were added 300 g of finely divided corn. The flask and its contents were then sterilized and after sterilization 150 ml of sterile deionized water were added. To the mixture in the flask were then added 45 ml of the inoculum prepared by the process and the material was thoroughly mixed. The mixed material was then incubated for about 20 days at 25°C in a dark room in a water-saturated atmosphere. The following illustrates the recovery of the anabolic substance from the fermentation medium.
A 300 g portion of fermented material was placed in 500 ml of deionized water and slurried. The slurry was then heated for about 15 minutes at 75°C, 300 g of filter aid were then added and the material was filtered. The solid filtered material containing the anabolic substance was then air dried, and 333 g of the dried cake were then extracted with 500 ml of ethanol. This procedure was repeated three more times. The ethanol extract was then dried under vacuum to give 6.84 g of solid material. This solid material was then dissolved in 20 ml of chloroform and extracted with 30 ml of an aqueous solution containing 5% by weight of sodium carbonate having an adjusted pH of about 11.2. The extraction process was repeated seven more times. The pH of the sodium carbonate extract was then adjusted to 6.2 with hydrochloric acid, to yield an anabolic substance containing precipitate. The precipitate and the aqueous sodium carbonate extract were then each in turn extracted with 75 ml of ethyl ether. This procedure was repeated three more times to yield a light yellow ethereal solution, which was then dried to yield 116 mg of solid anabolic substance. This material was then subjected to multiple transfer countercurrent distribution using 100 tubes and a solvent system consisting of two parts chloroform and two parts methanol and one part water as the upper phase, all parts by volume. The solid material obtained from the multiple transfer counter-current distribution was then tested for physiological activity according to the well-known mouse-uterine test. The fermentation estrogenic substance produced has the formula:
Tetrahydro F.E.S. was produced by dissolving 0.5 g F.E.S. in 200 ml of ethanol. The F.E.S. was reduced by contacting the solution with hydrogen for 3 hours at 30°C and 1,000 psi using 2 g of Raney nickel as a catalyst. After filtering and concentrating the reaction mixture, the product was washed with 2 to 3 ml of 2-nitropropane and crystallized. It was found to have a melting point from 143°C to 160°C.

brand name

Ralabol (Pitman-Moore); Ralgro (Pitman-Moore).

Therapeutic Function

Estrogen

General Description

White fluffy powder.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Zeranol is an alcohol. Flammable and/or toxic gases are generated by the combination of alcohols with alkali metals, nitrides, and strong reducing agents. They react with oxoacids and carboxylic acids to form esters plus water. Oxidizing agents convert them to aldehydes or ketones. Alcohols exhibit both weak acid and weak base behavior. They may initiate the polymerization of isocyanates and epoxides.

Health Hazard

ACUTE/CHRONIC HAZARDS: When heated to decomposition Zeranol emits acrid smoke and irritating fumes.

Fire Hazard

Flash point data for Zeranol are not available; however, Zeranol is probably combustible.

Safety Profile

An experimental teratogen. Experimental reproductive effects. Mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.