17924-92-4

Usage

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.

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-

Upstream product

• 10497-40-2 2,4-Dimethoxy-zearalenone 
• 132297-27-9 (S)-2,4-bis<(2-methoxyethoxy)methyl>zearalenone 
• 132260-57-2 4,6-bis<<(2-methoxyethoxy)methyl>oxy>-2-iodobenzoic acid 
• 130625-81-9 Methyl 2,4-dimethoxy-6-(E-prop-1-enyl)benzoate 
• 17924-91-3 2,4-Dimethoxy-6-(E-prop-1-enyl)benzoic acid 
• 130625-82-0 2,4-Dimethoxy-6-((E)-propenyl)-benzoyl chloride 
• 130625-84-2 (2S)-6-Oxohexan-2-yl 2,4-dimethoxy-6-(E-prop-1-enyl)benzoate 
• 130625-86-4 (2S)-6-Oxooct-7-en-2-yl 2,4-dimethoxy-6-(E-prop-1-enyl)benzoate 
• 70719-51-6 methyl 2,4-dimethoxy-6-<(phenylthio) methyl>-benzoate 
• 130625-85-3 (2S,6RS)-6-Hydroxyoct-7-en-2-yl 2,4-dimethoxy-6-(E-prop-1-enyl)benzoate 
• 130625-87-5 (2S)-6-Oxooct-7-en-2-yl 2,4-dimethoxy-6-<3-bromoprop-1-(E)-enyl>benzoate 
• 130625-83-1 (2S)-5-(Dithian-2-yl)pentan-2-yl 2,4-dimethoxy-6-(E-prop-1-enyl)benzoate 
• 130625-80-8 Methyl 2,4-dimethoxy-6-<1-(phenylthio)propyl>benzoate 
• 64584-92-5 (R)-pent-4-en-2-ol 

Downstream Products

• 5975-78-0 zearalanone 
• 10497-40-2 2,4-Dimethoxy-zearalenone 
• 71030-11-0 beta-zearalenol 
• 36455-72-8 α-zearalenol 
• 40785-64-6 (8'R,10'S)-8'-hydroxyzearalenone 
• 36455-70-6 cis-Zearalenone 
• 42422-68-4 taleranol 
• 26538-44-3 zeranol 
• 1032558-19-2 zearalenone 4-O-β-D-glucuronide 
• 1644064-13-0 14-O-(p-methoxybenzyl)zearalenone 
• 1644064-25-4 C₄₀H₄₈O₁₅ 
• 36455-71-7 Z-7α-zearalenol 
• 38055-76-4 7β-cis-zearalenol 
• 5975-86-0 4-methoxy-β-zearalenol 

Relevant academic research and scientific papers

A Short and Efficient Approach for the Total Synthesis of (S)-Zearalenone and (R)-De-O-methyllasiodiplodin by Using Stille and RCM Protocols

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.

Catalytic asymmetric total synthesis of (S)-(-)-zearalenone, a novel lipoxygenase inhibitor

A catalytic asymmetric synthesis of (S)-(-)-zearalenone is reported using asymmetric allylic alkylation for the introduction of the stereocenter. (S)-(-)-Zearalenone turned out to be a novel lipoxygenase inhibitor.

A concise total synthesis of (S)-zearalenone and zeranol

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

A novel biomimetic synthesis of (S)-(-)-zearalenone: Via macrocyclization and transannular aromatization

On heating, a hydroxy-keto-dioxinone underwent retro-Diels-Alder fragmentation and the resultant α,γ-diketo-ketene was efficiently trapped intramolecularly by a secondary alcohol to provide a macrocyclic triketo-lactone. Following ketal hydrolysis, transannular aromatization gave the resorcylate natural product, (S)-(-)-zearalenone.

Solid-phase synthesis of macrocyclic systems by a cyclorelease strategy: Application of the stille coupling to a synthesis of (S)-zearalenone

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

Total Synthesis of the Mycotoxin (-)-Zearalenone based on Macrocyclisation using a Cinnamyl Radical Intermediate

A concise synthesis of optically active (-)-zearalenone, which uses a novel 14-endo-trig macrocyclisation from a cinnamyl radical intermediate onto an α,β-enone electrophore as a key feature, is described.

Synthesis of β-Resorcylic Macrolides via Organopalladium Chemistry. Application to the Total Synthesis of (S)-Zearalenone

The β-resorcyclic macrolides are a class of naturally occurring 12- and 14-membered macrolides.Zearalenone (1), a 14-membered macrolide of this type, displays useful biological activity, which has led to great synthetic interest.In this paper the intramolecular coupling reaction of an organostannane with an electrophile is used to construct β-resorcylic macrolides.The intramolecular coupling of an aryl iodide with a vinylstannane provided the highest yield of lactones.This methodology was then used to prepare (S)-zearalenone (1).

Thermostable Enzymes in Organic Synthesis, Part 6. Total synthesis of (S)-(-)-Zearalenone using a TBADH-Generated Trifunctional Chiron

Chiral alcohols produced by Thermoanaerobium brockii alcohol dehydrogenase (TBADH)-catalysed asymmetric reduction of polyfunctional ketones are useful building blocks for natural products synthesis.In particular, the ability of TBADH to discriminate between two ketones having equal chemical reactivity is demonstrated by enzymatic reduction of dec-9-ene-2,6-dione to produce optically pure (S)-2-hydroxydec-9-en-6-one.The total synthesis of (S)-(-)-zearalenone with optical purity that exceeds 99.5percent has been achieved by using the latter compound as a starting material.

Steroid ethers

Novel steroid ethers are disclosed, which are represented by the formula: STR1 wherein Z is selected from the group consisting of >C=O >CHOH, and STR2 X is selected from the group consisting of --H and --OH, and R is selected from the group consisting of