36455-72-8

Basic information

• Product Name: ALPHA-ZEARALENOL
• Synonyms: ZEARALENOL;ALPHA-ZEARALENOL;2,4-DIHYDROXY-6-[6ALPHA,10-DIHYDROXY-TRANS-1-UNDECENYL]BENZOIC ACID MICRO-LACTONE;2,4-Dihydroxy-6-(6α,10-dihydroxy-trans-1-undecenyl)benzoic acid μ-lactone;A-ZEARALENOL;(3S,7R,11E)-3,4,5,6,7,8,9,10-Octahydro-7,14,16-trihydroxy-3-methyl-1H-2-benzoxacyclotetradecin-1-one;trans-α-Zearalenol;1H-2-Benzoxacyclotetradecin-1-one, 3,4,5,6,7,8,9,10-octahydro-7,14,16-trihydroxy-3-methyl-, (3S-(3R*,7S*,11E))-
• CAS NO: 36455-72-8
• Molecular Formula: C18H24O5
• Molecular Weight: 320.38
• EINECS: 200-835-2
• Product Categories: Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals
• Mol File: 36455-72-8.mol

Chemical Properties

• Melting Point: 158-161°C
• Boiling Point: 599°Cat760mmHg
• Flash Point: 2℃
• Appearance: /
• Density: 1.174g/cm³
• Vapor Pressure: 3.4E-15mmHg at 25°C
• Refractive Index: 1.548
• Storage Temp.: 2-8°C
• Solubility: ≤20mg/ml in ethanol;30mg/ml in DMSO;30mg/ml in dimethyl formamide
• PKA: 7.61±0.60(Predicted)
• CAS DataBase Reference: ALPHA-ZEARALENOL(CAS DataBase Reference)
• NIST Chemistry Reference: ALPHA-ZEARALENOL(36455-72-8)
• EPA Substance Registry System: ALPHA-ZEARALENOL(36455-72-8)

Safety Data

• Hazard Codes: Xn,T,F
• Statements: 20/21/22-40-52/53-68/20/21/22-36-11-62-48/20-63-46-45
• Safety Statements: 36/37-61-16-45-53
• RIDADR: UN 1648 3 / PGII
• WGK Germany: 3
• F: 8
• Hazardous Substances Data: 36455-72-8(Hazardous Substances Data)

Usage

Uses

Used in Analytical Chemistry:
ALPHA-ZEARALENOL is used as an analytical reference standard for the determination of the analyte in traditional medicinal herbs, human and animal urine by various chromatography techniques. This application aids in identifying and quantifying the presence of this mycotoxin in samples, ensuring food safety and quality.
Used in Food Quality and Safety:
ALPHA-ZEARALENOL is a critical factor in assessing the quality and safety of grains, especially maize, which is susceptible to contamination by Fusarium species. Monitoring and controlling the levels of zearalenol in the food supply is essential to minimize potential health risks associated with its consumption.
Used in Research and Development:
As a mycotoxin with significant estrogenic activity, ALPHA-ZEARALENOL is used in research and development to study its effects on uterotropic activity, sperm motility, and preimplantation embryonic development. Understanding these effects can contribute to the development of strategies to mitigate the impact of mycotoxins on human and animal health.
Used in Environmental and Agricultural Studies:
ALPHA-ZEARALENOL is also used in environmental and agricultural studies to investigate the prevalence of Fusarium species in various ecosystems and their impact on crop quality. This information can help in developing effective pest management strategies and improving agricultural practices to reduce the risk of mycotoxin contamination in the food supply.

Biochem/physiol Actions

α-Zearalenol (α-ZOL) is a catabolite of zearalenone, synthesized majorly in granulosa cells, intestine and liver in pigs. It has estrogenic functionality. α-ZOL inhibits sperm motility in horse possibly by eliciting genotoxic effect. α-ZOL displays higher affinity towards estrogenic receptors.

in vitro

the binding characteristic of α-zea was less potent with estrogen receptors than the parent compound [2]. α-zearalenol showed pronounced effects on uterotropic activity [3]. α-zea inhibited normal sperm motility, but stimulated hyperactive motility in the remaining motile cells and simultaneously induced the acrosome reaction [4].

references

[1]. zinedine a, soriano j m, molto j c, et al. review on the toxicity, occurrence, metabolism, detoxification, regulations and intake of zearalenone: an oestrogenic mycotoxin[j]. food and chemical toxicology, 2007, 45(1): 1-18.[2]. kiang d t, kennedy b j, pathre s v, et al. binding characteristics of zearalenone analogs to estrogen receptors[j]. cancer research, 1978, 38(11 part 1): 3611-3615.[3]. mirocha c j, pathre s v, behrens j, et al. uterotropic activity of cis and trans isomers of zearalenone and zearalenol[j]. applied and environmental microbiology, 1978, 35(5): 986-987.[4]. filannino a, stout t a e, gadella b m, et al. dose-response effects of estrogenic mycotoxins (zearalenone, alpha-and beta-zearalenol) on motility, hyperactivation and the acrosome reaction of stallion sperm[j]. reproductive biology and endocrinology, 2011, 9(1): 134.

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

• 17924-92-4 zearalenone 
• 445380-26-7 methyl 4,6-bis[(2-methoxyethoxy)methyloxy]-2-[(1'E,6'R,10'S)-6',10'-bis(tert-butyldimethylsilyloxy)undec-1'-en-1'-yl]benzoate 
• 445380-27-8 methyl 4,6-bis[(2-methoxyethoxy)methyloxy]-2-[(1'E,6'R,10'S)-6',10'-dihydroxyundec-1'-en-1'-yl]benzoate 
• 445380-28-9 4,6-bis[(2-methoxyethoxy)methyloxy]-2-[(1'E,6'R,10'S)-6',10'-dihydroxyundec-1'-en-1'-yl]benzoic acid 
• 311805-54-6 (5R,9S)-5,9-bis(tert-butyldimethylsilyloxy)decan-1-ol 
• 311805-75-1 (5S,9S)-5,9-bis(tert-butyldimethylsilyloxy)decanal 
• 311805-71-7 diethyl (6-benzyloxy-2-oxo-1-hexyl)phosphonate 
• 445380-24-5 (1'E,4R,5S)-4-(7'-benzyloxy-3'-oxohept-1'-en-1'-yl)-2,2,5-trimethyl-1,3-dioxolane 
• 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 
• 445380-25-6 (6E,8S,9S)-1-benzyloxy-8,9-dihydroxydec-6-en-5-one 
• 445380-29-0 2,4-bis[(2-methoxyethoxy)methyl]-α-zearalenol 
• 144402-24-4 zearalenol 7α,β-O-chloroacetyl ester 

Downstream Products

• 5975-86-0 4-methoxy-α-zearalenol 
• 26538-44-3 zeranol 
• 36455-71-7 Z-7α-zearalenol 

Relevant articles and documents

Synthesis and cytotoxic activities of semisynthetic zearalenone analogues

Zearalenone is a β-resorcylic acid macrolide with various biological activities. Herein we report the synthesis and cytotoxic activities of 34 zearalenone analogues against human oral epidermoid carcinoma (KB) and human breast adenocarcinoma (MCF-7) cells as well as noncancerous Vero cells. Some zearalenone analogues showed moderately enhanced cytotoxic activities against the two cancer cell lines. We have discovered the potential lead compounds with diminished or no cytotoxicity to Vero cells. Preliminary structure–activity relationship studies revealed that the double bond at the 1′ and 2′ positions of zearalenone core was crucial for cytotoxic activities on both cell lines. In addition, for zearalenol analogues, the unprotected hydroxyl group at C-2 and an alkoxy substituent at C-4 played key roles on cytotoxic effects of both cell lines.

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.

Preparative enzymatic synthesis of glucuronides of zearalenone and five of its metabolites

The resorcylic acid lactones zearalenone (1), α-zearalenol (2), β-zearalenol (3), α-zearalanol (zeranol) (4), β-zearalanol (taleranol) (5), and zearalanone (6) were converted to their glucuronides on a preparative scale in good yields. Reactions were conducted with bovine uridine 5′-diphosphoglucuronyl transferase (UDPGT) as catalyst and uridine 5′-diphosphoglucuronic acid (UDPGA) as cofactor. The glucuronides were isolated by column chromatography and characterized by NMR spectroscopy and mass spectrometry. Although the principal products were 4-O-glucuronides (i.e., linkage through a phenolic hydroxyl), significant quantities of the 6′-O-glucuronides (i.e., linkage through the aliphatic hydroxyl) of alcohols 2, 4, and 5 were also isolated. In the case of 3, the 2-O-glucuronide was isolated as the minor product. Overall isolated yields of glucuronides, performed on a 20-50 mg scale, were typically ca. 80% based on the resorcylic acid lactone starting material. LC-UV-MS2 analysis of purified specimens revealed MS2 fragmentations useful for defining the point of attachment of the glucuronide moiety to the zearalenone nucleus.

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.

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

A highly stereoselective synthesis of α- and β-zearalenol 1 and 2 is accomplished utilising π-allyltricarbonyliron lactone complexes 5 and 6 to establish the 1,5-stereochemical relationship of oxygen functionalities present in the natural products. The Royal Society of Chemistry 2000.

Enzymatic kinetic separation of stereoisomeric macrocyclic lactone derivatives, 7α,β-O-acyl trans-zearalenols and 7α,β-O-acyl zearanols

Diastereomeric mixtures of resorcyclic acid macrocyclic lactones, 7α,β-O-acyl zearalenols (1,2 and 3,4 full name: trans-3,4,5,6,9,10-octahydro-14,16-dihydroxy-7-acyloxy-3-methyl 1H-2-benzoxacyclotetradecin-1-ones (3S,7S or 3S,7R)), and 7α,β-acyl zearanols

Microbial Transformation of Zearalenone. 2. Reduction, Hydroxylation, and Methylation Products

Microbial transformations have been employed as a means of preparing analogues of the resorcylic acid lactone zearalenone.Microbial transformation products were initially identified by thin-layer chromatography of fermentation extracts and then prepared by large-scale incubations.Each metabolite was subjected to structural elucidation employing carbon-13 and proton NMR, mass spectrometry, and infrared analysis.Metabolites were identified as α- and β-zearalenol, α- and β-zearalanol, zearalanone, 8'(S)-hydroxyzearalenone, 2,4-dimethoxyzearalenone, and 2-methoxyzearalenone.Binding affinities to rat uterine estrogen receptors were carried out.Only those metabolites having a free 4-phenolic group were capable of binding to the estrogen receptor.However, 8'-hydroxyzearalenone, even with a 4-phenolic hydroxyl, did not bind to the receptor.It is possible that hydrogen bonding of the aliphatic hydroxyl groups to the C-6' carbonyl of zearalenone or equilibrium between the hydroxy ketone and its tautomeric hemiketal may lead to distortion of the conformation of the molecule resulting in loss of binding to the receptor.