71030-11-0

Basic information

• Product Name: BETA-ZEARALENOL
• Synonyms: BETA-ZEARALENOL;2,4-DIHYDROXY-6-[6BETA,10-DIHYDROXY-TRANS-1-UNDECENYL]BENZOIC ACID MICRO-LACTONE;B-zearalenol;(3S,7S,11E)-3,4,5,6,7,8,9,10-Octahydro-7,14,16-trihydroxy-3-methyl-1H-2-benzoxacyclotetradecin-1-one;1H-2-Benzoxacyclotetradecin-1-one, 3,4,5,6,7,8,9,10-octahydro-7,14,16-trihydroxy-3-methyl-, (3S-(3R*,7R*,11E))-;1H-2-Benzoxacyclotetradecin-1-one, 3,4,5,6,7,8,9,10-octahydro-7,14,16-trihydroxy-3-methyl-, (3S,7S,11E)-;(3S,7S,11E)-;(-)-beta-Zearalenol, beta-Trans-Zearalenol
• CAS NO: 71030-11-0
• Molecular Formula: C18H24O5
• Molecular Weight: 320.38
• EINECS: 200-835-2
• Product Categories: Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;Bioactive Small Molecules;Building Blocks;Carbonyl Compounds;Cell Biology;Chemical Synthesis;Lactones;Organic Building Blocks;Z
• Mol File: 71030-11-0.mol
• Article Data: 8

Chemical Properties

• Melting Point: 137-139°C
• Boiling Point: 599°C at 760 mmHg
• Flash Point: 2℃
• Appearance: /
• Density: 1.174g/cm³
• Vapor Pressure: 3.4E-15mmHg at 25°C
• Refractive Index: 1.548
• Storage Temp.: −20°C
• BRN: 3653579
• CAS DataBase Reference: BETA-ZEARALENOL(CAS DataBase Reference)
• NIST Chemistry Reference: BETA-ZEARALENOL(71030-11-0)
• EPA Substance Registry System: BETA-ZEARALENOL(71030-11-0)

Safety Data

• Hazard Codes: Xn,N,F
• Statements: 20/21/22-40-52/53-68/20/21/22-50-36-22-11
• Safety Statements: 36/37-61-36-16
• RIDADR: UN 3077 9 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 71030-11-0(Hazardous Substances Data)

Usage

Description

β-Zearalenol is a hepatic metabolite of zearalenone , a mycotoxin produced by fungi in food and animal feeds. It is a less potent agonist of estrogen receptors than the parent compound. However, β-zearalenol has pronounced effects on uterotropic activity and sperm acrosome reaction.

Chemical Properties

White Solid

Uses

Different sources of media describe the Uses of 71030-11-0 differently. You can refer to the following data:
1. Reactant involved in biological studies including:? ;Synthesis of amino glycoside nucleotides1? ;Enzymatic synthesis of glucuronides of zearalenone2? ;Derivatization of Zearalenone3,4,5
2. β-Zearalenol is a mycotoxin produced by several species of Fusarium. β-Zearalenol exhibits pronounced estrogenic activity, like other zearalenones. Contamination of grains by Fusarium species, notably maize, gives rise to high levels of zearalenol and is regarded as an important food quality issue for both human and animal health.
3. The more active Zearalenone (Z270500) metabolite.

InChI:InChI=1/C18H24O5/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/h3,7,10-12,14,19-21H,2,4-6,8-9H2,1H3/b7-3+/t12-,14-/m0/s1

Upstream product

• 445380-25-6 (6E,8S,9S)-1-benzyloxy-8,9-dihydroxydec-6-en-5-one 
• 311805-52-4 (1'E,2RS,4S,5S)-4-(7'-benzyloxy-3'-oxohept-1'-en-1'-yl)-5-methyl-1,3-dioxa-2-thiolane 2-oxide 
• 445380-24-5 (1'E,4R,5S)-4-(7'-benzyloxy-3'-oxohept-1'-en-1'-yl)-2,2,5-trimethyl-1,3-dioxolane 
• 311805-71-7 diethyl (6-benzyloxy-2-oxo-1-hexyl)phosphonate 
• 445380-32-5 4,6-bis[(2-methoxyethoxy)methyloxy]-2-[(1'E,6'S,10'S)-6',10'-dihydroxyundec-1'-en-1'-yl]benzoic acid 
• 445380-31-4 methyl 4,6-bis[(2-methoxyethoxy)methyloxy]-2-[(1'E,6'S,10'S)-6',10'-dihydroxyundec-1'-en-1'-yl]benzoate 
• 445380-30-3 methyl 4,6-bis[(2-methoxyethoxy)methyloxy]-2-[(1'E,6'S,10'S)-6',10'-bis(tert-butyldimethylsilyloxy)undec-1'-en-1'-yl]benzoate 
• 17924-92-4 zearalenone 
• 1604028-37-6 (2R,6S)-6-(tert-butyldimethylsilyloxy)heptane-1,2-diol 
• 393109-13-2 (S)-tert-butyl(hept-6-en-2-yloxy)dimethylsilane 
• 1204755-29-2 4,6-dimethoxy-2-vinyl-benzoic acid 
• 17846-90-1 methyl 2-formyl-4,6-dimethoxybenzoate 
• 6110-37-8 methyl 2,4-dimethoxy-6-methylbenzoate 
• 3187-58-4 methyl orsellinate 

Downstream Products

• 5975-86-0 4-methoxy-β-zearalenol 
• 42422-68-4 taleranol 
• 38055-76-4 7β-cis-zearalenol 

Relevant articles and documents

Enantioselective total synthesis of β-zearalenol from (s)-propylene oxide

The total synthesis of 14-membered resorcylic acid macrolide, β-zearalenol, was accomplished starting from commercially available enantiomerically pure propylene oxide and methyl 2,4-dihydroxy-6-methylbenzoate using Grignard reaction, asymmetric dihydroxy

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.

The use of π-allyltricarbonyliron lactone complexes in the synthesis of the resorcylic macrolides α- and β-zearalenol

A highly stereoselective synthesis of the natural products α- and β-zearalenol 1 and 2 has been achieved using π-allyltricarbonyliron lactone complexes to control the 1,5-stereochemical relationship of the oxygen functionalities found in these resorcylic macrolides.