17924-92-4 Usage
Description
Zearalenone, also known as F-2 toxin, is a resorcylic acid lactone produced by Fusarium species of fungi. It is a potent estrogenic mycotoxin and an estrogen receptor activator. Zearalenone is a white microcrystalline solid or powder and is a macrolide with a fourteen-membered lactone fused to 1,3-dihydroxybenzene. It acts as a non-steroidal estrogen, binding to estrogen receptors and causing uterotropic effects. Zearalenone is commonly found in contaminated grains, particularly maize, and poses a significant food quality and health issue for both humans and animals.
Uses
Used in Research Applications:
Zearalenone is used as a research tool in the study of estrogenic effects and endocrine disruption. It helps researchers understand the mechanisms of estrogen receptor binding and the impact of phytoestrogens on various biological processes.
Used in Food Safety and Quality Control:
Zearalenone is used as an indicator of mycotoxin contamination in grains, particularly maize. Monitoring and controlling zearalenone levels in food products is essential to ensure food safety and quality for both human and animal consumption.
Used in Animal Health and Nutrition:
Zearalenone is used as a marker for assessing the risk of reproductive problems and hepatic tumors in animals due to its estrogenic effects. It helps in the development of strategies to mitigate the impact of mycotoxin contamination on animal health and nutrition.
Used in Environmental and Agricultural Studies:
Zearalenone is used in studies related to the impact of Fusarium species on crop health and the environment. Understanding the factors that contribute to the production of zearalenone by Fusarium fungi can help in developing strategies for managing mycotoxin contamination in agricultural practices.
Air & Water Reactions
Zearalenone may be sensitive to prolonged exposure to air. Insoluble in water.
Reactivity Profile
Zearalenone is an ester. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides. Zearalenone may be incompatible with alkalis.
Fire Hazard
Flash point data for Zearalenone are not available. Zearalenone is probably combustible.
Biochem/physiol Actions
Zearalenone, a fungal mycotoxin produced by Fusarium, binds the estrogen receptor (ER) and is uterotropic in the newborn rat. It is a common contaminant in cereal grain used for animal and human food, and exerts an estrogenic activity that modulates/disrupts endocrine function in animals and possibly humans.
Metabolic pathway
When zearalenone is subjected to microbial
transformation by a fungus, Gliocladium roseum, it is
converted to a 1 : 1 mixture of 1-(3,5-dihydroxyphenyl)-
10 0 -hydroxy-1-undecen-6'-one and 1-(3,5-
dihydroxyphenyl)-6'-hydroxy-1-undecen-10'-one.
Check Digit Verification of cas no
The CAS Registry Mumber 17924-92-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,7,9,2 and 4 respectively; the second part has 2 digits, 9 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 17924-92:
(7*1)+(6*7)+(5*9)+(4*2)+(3*4)+(2*9)+(1*2)=134
134 % 10 = 4
So 17924-92-4 is a valid CAS Registry Number.
InChI: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-
17924-92-4Relevant articles and documents
A Short and Efficient Approach for the Total Synthesis of (S)-Zearalenone and (R)-De-O-methyllasiodiplodin by Using Stille and RCM Protocols
Kumar Dey, Sujit,Ataur Rahman, Mohammad,Alkhazim Alghamdi, Ahmad,Reddy, Basi V. Subba,Yadav, Jhillu S.
, p. 1684 - 1692 (2016/04/05)
A concise, flexible, and linear approach has been devised for the total synthesis of the resorcinylic acid lactones (S)-zearalenone (2) and (R)-de-O-methyllasiodiplodin (4) by using a Stille cross-coupling strategy. The other key steps of the synthesis include a ring-closing metathesis (RCM), a chemoselective reduction of an α,β-unsaturated ketone, and a transesterification reaction.
A concise total synthesis of (S)-zearalenone and zeranol
Yadav,Murthy, P. Vishnu
, p. 2117 - 2124 (2011/08/05)
A convergent total synthesis of the naturally occurring, 14-membered macrolides (S)-zearalenone and zeranol has been achieved through application of the Diels-Alder reaction, Jacobsen kinetic resolution, Mitsunobu coupling, ring-closing metathesis, and hy
Solid-phase synthesis of macrocyclic systems by a cyclorelease strategy: Application of the stille coupling to a synthesis of (S)-zearalenone
Nicolaou,Winssinger, Nicolas,Pastor, Joaquin,Murphy, Fiona
, p. 2534 - 2537 (2007/10/03)
No heteroatom required! In many solid-phase syntheses, after the release from the polymer support a heteroatom (e.g. O, S, N) remains in the substrate as a residue of a linking protecting group. With polymer-bound tin reagents cleavage and cyclization of
