36455-72-8 Usage
Description
ALPHA-ZEARALENOL, a mycotoxin produced by various species of Fusarium, is a significant concern for both human and animal health due to its contamination of grains, particularly maize. It exhibits potent estrogenic activity, being three times more active than zearalenone, and is a major hepatic metabolite of zearalenone, a mycotoxin found in food and animal feeds. ALPHA-ZEARALENOL is an off-white solid with pronounced effects on uterotropic activity, sperm motility, and preimplantation embryonic development.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 36455-72-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,6,4,5 and 5 respectively; the second part has 2 digits, 7 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 36455-72:
(7*3)+(6*6)+(5*4)+(4*5)+(3*5)+(2*7)+(1*2)=128
128 % 10 = 8
So 36455-72-8 is a valid CAS Registry Number.
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
36455-72-8Relevant articles and documents
Synthesis and cytotoxic activities of semisynthetic zearalenone analogues
Tadpetch, Kwanruthai,Kaewmee, Benyapa,Chantakaew, Kittisak,Kantee, Kawalee,Rukachaisirikul, Vatcharin,Phongpaichit, Souwalak
supporting information, p. 3612 - 3616 (2016/07/21)
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.
Preparative enzymatic synthesis of glucuronides of zearalenone and five of its metabolites
Stevenson, David E.,Hansen, Richard P.,Loader, Jared I.,Jensen, Dwayne J.,Cooney, Janine M.,Wilkins, Alistair L.,Miles, Christopher O.
experimental part, p. 4032 - 4038 (2010/03/31)
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
Ley, Steven V.,Burckhardt, Svenja
, p. 3028 - 3030 (2007/10/03)
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.
