36455-71-7

Basic information

• Product Name: cis-Zearalenol
• CAS NO: 36455-71-7
• Mol File: 36455-71-7.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: cis-Zearalenol(CAS DataBase Reference)
• NIST Chemistry Reference: cis-Zearalenol(36455-71-7)
• EPA Substance Registry System: cis-Zearalenol(36455-71-7)

Safety Data

• Hazardous Substances Data: 36455-71-7(Hazardous Substances Data)

Upstream product

• 194795-92-1 7α,β-trans-zearalenol 
• 36455-70-6 cis-Zearalenone 
• 17924-92-4 zearalenone 
• 36455-72-8 α-zearalenol 

Relevant articles and documents

In vitro phase i metabolism of cis -zearalenone

The present study investigates the in vitro phase I metabolism of cis-zearalenone (cis-ZEN) in rat liver microsomes and human liver microsomes. cis-ZEN is an often ignored isomer of the trans-configured Fusarium mycotoxin zearalenone (trans-ZEN). Upon the influence of (UV-) light, trans-ZEN isomerizes to cis-ZEN. Therefore, cis-ZEN is also present in food and feed. The aim of our study was to evaluate the in vitro phase I metabolism of cis-ZEN in comparison to that of trans-ZEN. As a result, an extensive metabolization of cis-ZEN is observed for rat and human liver microsomes as analyzed by HPLC-MS/MS and high-resolution MS. Kinetic investigations based on the substrate depletion approach showed no significant difference in rate constants and half-lives for cis- and trans-ZEN in rat microsomes. In contrast, cis-ZEN was depleted about 1.4-fold faster than trans-ZEN in human microsomes. The metabolite pattern of cis-ZEN revealed a total of 10 phase I metabolites. Its reduction products, α- and β-cis-zearalenol (α- and β-cis-ZEL), were found as metabolites in both species, with α-cis-ZEL being a major metabolite in rat liver microsomes. Both compounds were identified by co-chromatography with synthesized authentic standards. A further major metabolite in rat microsomes was monohydroxylated cis-ZEN. In human microsomes, monohydroxylated cis-ZEN is the single dominant peak of the metabolite profile. Our study discloses three metabolic pathways for cis-ZEN: reduction of the keto-group, monohydroxylation, and a combination of both. Because these routes have been reported for trans-ZEN, we conclude that the phase I metabolism of cis-ZEN is essentially similar to that of its trans isomer. As trans-ZEN is prone to metabolic activation, leading to the formation of more estrogenic metabolites, the novel metabolites of cis-ZEN reported in this study, in particular α-cis-ZEL, might also show higher estrogenicity.