17924-92-4 Usage
Chemical Properties
Crystalline Solid
Uses
Different sources of media describe the Uses of 17924-92-4 differently. You can refer to the following data:
1. Zearalenone is a resorcylic acid lactone produced by a number of Fusarium sp.. Zearalenone acts as a non-steroidal estrogen, binding to estrogen receptor and is uterotropic. Zearalenone induces reproductive problems in animals and, in some animal models, is thought to be a primary initiator of hepatic tumours. In vivo, zearalenone undergoes metabolic reduction to the more estrogenic zearalenol. Contamination of grains, notably maize, by Fusarium species gives rise to high levels of zearalenone and is regarded as an important food quality issue for both humans and animal health.
2. A phytoestrogenic mycotoxin and ER activator
3. Estrogenic mycotoxin produced by Fusarium fungi commonly found in grains. One of a group of compounds known as resorcylic acid lactones
Definition
ChEBI: A macrolide comprising a fourteen-membered lactone fused to 1,3-dihydroxybenzene; a potent estrogenic metabolite produced by some Giberella species.
General Description
White microcrystals or white powder.
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
experimental part, 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
