3718 (S,E)-Zearalenone cis-Zearalenone is a metabolite of Fusarium species. 17924-92-4 5375083 C18H22O5 White crystalline solid. 164 - 165°C Oral, dermal, inhalation, and parenteral (contaminated drugs). (A3101) Zearalenone's genotoxicity results from it's ability to cause DNA fragmentation, chromosome aberrations, and DNA adduct formation. It exerts cytotoxic effects by enhancing lipid peroxidation, increasing oxidative stress, and inducing apoptosis. Zearalenone also has significant estrogenic activity, causing severe reproductive problems in animals. In humans, Zearalenone has been shown to cause an earlier onset of puberty in children, endometrial adenocarcinomas, hyperplasia and breast cancer in women. Mycotoxins are often able to enter the liver and kidney by human organic anion transporters (hOATs) and human organic cation transporters (hOCTs). They can also inhibit uptake of anions and cations by these transporters, interefering with the secretion of endogenous metabolites, drugs, and xenobiotics including themselves. This results in increased cellular accumulation of toxic compounds causing nephro- and hepatotoxicity. (A2960, A3014) Zearalenone is rapidly absorbed after oral administration. In humans, most of the zearalenone absorbed is not metabolized. The main metabolites include alpha- and beta-zeralenol, and the glucuronide conjugates of both the parent compound and its metabolites. Zearalenone and its metabolites are excreted mainly in the bile. (A741, L1912) LD50: >2000 mg/kg (Oral, Mouse) (L1912) LD50: >500 mg/kg (Intraperitoneal, Mouse) (L1912) 3, not classifiable as to its carcinogenicity to humans. (L135) Zearalenone (ZEA), also known as RAL and F-2 mycotoxin, is a potent estrogenic metabolite produced by some Giberella species. Several Fusarium species also produce zearalenone as their primary toxin. It can be found worldwide in a number of cereal crops, such as maize, barley, oats, wheat, rice, and sorghum, and also in bread. (L1947) Zearalenone is a reproductive toxin and has been shown to cause infertility, abortion or other breeding problems in livestock. In humans it can cause earlier onset of puberty in children, endometrial adenocarcinomas, hyperplasia, and breast cancer in women. Zearalenone is also immunotoxic, genotoxic, and can cause kidney and liver damage. (L1947, A2960) 2009-12-22T23:09:04Z 2014-12-24T20:26:19Z http://en.wikipedia.org/wiki/Zearalenone C09981 true Dehydrogenase/reductase SDR family member 9 (Q9BPW9) (A2897) [H]\C1=C([H])/C2=CC(O)=CC(O)=C2C(=O)OC(C)CCCC(=O)CCC1 C18H22O5 InChI=1/C18H22O5/c1-12-6-5-9-14(19)8-4-2-3-7-13-10-15(20)11-16(21)17(13)18(22)23-12/h3,7,10-12,20-21H,2,4-6,8-9H2,1H3/b7-3+ InChIKey=MBMQEIFVQACCCH-XVNBXDOJNA-N 318.3643 318.146723814 Exogenous Solid HMDB31752 4524664