ZEARALENONE

PRODUCT IDENTIFICATION

CAS NO.

17924-92-4

ZEARALENONE 

EINECS NO.

241-864-0

FORMULA C18H22O5

MOL WT. 318.36

H.S. CODE

2932.20.2000

TOXICITY

 
SYNONYMS

Zearalenone; Zenone; trans-Zearalenone;

(-)-Zearalenone; (10S)-Zearalenone; (S)-(-)-Zearalenone; (S)-Zearalenone; 6-(10-Hydroxy-6-oxo-trans-1-undecenyl)-beta-resorcylic acid lactone; trans-14,16-Dihydroxy-3-methyl-7-oxobenzoxacyclotetradec-11-en-1-one; trans-6-(10-Hydroxy-6-oxo-1-undecenyl)resorcylic acid mu-lactone; Other RN: 18695-28-8

SMILES

c12c(cc(cc2O)O)C=CCCCC(=O)CCC[C@@H](OC1=O)C 

CLASSIFICATION

Non-steroidal estrogen

EXTRA NOTES

One of a group of compounds known under the general designation of resorcylic acid lactones. Cis, trans, dextro and levo forms have been isolated from the fungus Gibberella zeae (formerly Fusarium graminearum). They have estrogenic activity, cause toxicity in livestock as feed contaminant, and have been used as anabolic or estrogen substitutes.

PHYSICAL AND CHEMICAL PROPERTIES

PHYSICAL STATE white powder
MELTING POINT 164 ~ 165 C
BOILING POINT  
SPECIFIC GRAVITY  
SOLUBILITY IN WATER < 0.1 (g/100ml at 20 C)
SOLVENT SOLUBILITY

Slightly soluble in hexane. Soluble in benzene, acetonitrile, dichloromethane, methanol, acetone.

pH  
VAPOR DENSITY  

AUTOIGNITION

 

NFPA RATINGS

 

REFRACTIVE INDEX

 

FLASH POINT  
STABILITY Stable under ordinary conditions.

EXTERNAL LINKS & GENERAL DESCRIPTION

Wikipedia Linking

Google Scholar Search

Drug Information Portal (U.S. National Library of Medicine) - Zearalenone

PubChem Compound Summary - Zearalenone

IPCS INCHEM -  Zearalenone

Drug Bank -  Zearalenone

KEGG (Kyoto Encyclopedia of Genes and Genomes) -  Zearalenone

http://www.ebi.ac.uk/ -  Zearalenone

http://www.ncbi.nlm.nih.gov/ -  Zearalenone

http://www.sigmaaldrich.com/
Biochem/physiol Actions: Zearalenone, a fungal mycotoxin produced by Fusarium, binds the estrogen receptor (ER) and is uterotropic in the newborn rat. It is a common contaminant in cereal grain used for animal and human food, and exerts an estrogenic activity that modulates/disrupts endocrine function in animals and possibly humans.

http://www.ansci.cornell.edu/
Mycotoxins produced by Fusarium spp. are of two general types: 1) the nonestrogenic trichothecenes, including DON, nivalenol, T-2 toxin, and diacetoxyscripenol, and 2) the mycoestrogens, including Zearalenone (ZEN) and zearalenol . Zearalenone and zearalenol are both estrogenic resorcylic acid lactone compounds produced by the fungi Fusarium spp. (Diekman and Green, 1992) Despite their structural dissimilarity to the steriodal estrogens, ZEN and several of its derivatives possess estrogenic activity. ZEN undergoes a folding such that hydroxyl or potential hydroxyl groups become appropriately orientated to facilitate binding to tissue receptors that normally bind estrogens. Similar binding affinities for ZEN have been determined for the estrogen receptor in sheep and calf uterus.(Diekman and Green, 1992)

Local:
Zeranol is a non-steroidal estrogenic growth stimulant that is used in veterinary medicine and has been used for human. The use for growth promotion in food animals was banned in the EU. An anabolic-estrogenic agent promote cell growth and division, resulting in growth of muscle tissue and sometimes bone size and strength. Testosterone and androgen are examples. Zeranol is also called zearalenol as it is a reduction product of zearalenone, an estrogenic mycotoxin product. Oestradiol-17beta, testosterone, progesterone, and trebolne are also used as growth stimulants for food animals.

Non-steroidal estrogen analog

CAS RN

Equol 531-95-3
2-sec-Butylphenol 89-72-5
Diethylstilbestrol 56-53-1
Bisphenol A 80-05-7
Dienestrol 84-17-3
Coumestrol 479-13-0
Allenolic acid 553-39-9
Chlorotrianisene 569-57-3
4-Octylphenol 1806-26-4
Hexestrol 5635-50-7
Zearalenone 17924-92-4
Zeranol 26538-44-3
SALES SPECIFICATION

APPEARANCE

white powder
ASSAY

98.0% min

MELTING POINT

159 ~ 162 C

TRANSPORTATION
PACKING
 
HAZARD CLASS 8 (Packing Group: III)
UN NO. 1759
SAFETY INFORMATION

HAZARD OVERVIEW

OSHA Hazards:Target Organ Effect, Irritant, Teratogen, Reproductive hazard. Target Organs: Reproductive system.

GHS

 

SIGNAL WORD Danger

PICTOGRAMS

HAZARD STATEMENTS

H314-H361

P STATEMENTS

P280-P305 + P351 + P338-P310

EC DIRECTIVES

 

HAZARD CODES

RISK PHRASES

34

SAFETY PHRASES

26-36/37/39-45

PRICE INFORMATION