10497-40-2

Basic information

• Product Name: 2,4-O-Dimethylzearalenone
• Synonyms: (3S,11E)-3,4,5,6,9,10-Hexahydro-14,16-dimethoxy-3-methyl-1H-2-benzoxacyclotetradecin-1,7(8H)-dione;(3S,11E)-3,4,5,6,9,10-Hexahydro-3-methyl-14,16-dimethoxy-1H-2-benzoxacyclotetradecin-1,7(8H)-dione;(S)-Zearalenone dimethyl ether;(S,E)-3,4,5,6,9,10-Hexahydro-14,16-dimethoxy-3-methyl-1H-2-benzoxacyclotetradecin-1,7(8H)-dione;2,4-O-Dimethylzearalenone
• CAS NO: 10497-40-2
• Molecular Formula: C₂₀H₂₆O₅
• Molecular Weight: 346.42
• Mol File: 10497-40-2.mol
• Article Data: 12

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2,4-O-Dimethylzearalenone(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-O-Dimethylzearalenone(10497-40-2)
• EPA Substance Registry System: 2,4-O-Dimethylzearalenone(10497-40-2)

Safety Data

• Hazardous Substances Data: 10497-40-2(Hazardous Substances Data)

Usage

Naturally occurring mycotoxin

2,4-O-Dimethylzearalenone is a toxic compound produced by certain species of Fusarium fungi that can contaminate cereal crops.

Produced by Fusarium fungi

The mycotoxin is produced by several species of Fusarium fungi, which commonly grow on maize and wheat.

Derivative of zearalenone

2,4-O-Dimethylzearalenone is a structurally similar compound to the well-known mycotoxin zearalenone.

Toxic to animals and humans

2,4-O-Dimethylzearalenone has been found to be toxic to both animals and humans, with potential endocrine-disrupting and estrogenic effects.

Adverse reproductive and developmental effects

Exposure to 2,4-O-Dimethylzearalenone has been linked to negative reproductive and developmental outcomes.

Liver damage and immunotoxicity

The mycotoxin can also cause liver damage and negatively affect the immune system.

Regulatory limits

Due to the potential health risks associated with 2,4-O-Dimethylzearalenone, regulatory agencies have established maximum limits for its presence in food and feed products.

Control through agricultural practices and monitoring

Efforts to control the presence of 2,4-O-Dimethylzearalenone in agricultural products include good agricultural practices, regular monitoring, and proper storage conditions.

Upstream product

• 17924-92-4 zearalenone 
• 130625-87-5 (2S)-6-Oxooct-7-en-2-yl 2,4-dimethoxy-6-<3-bromoprop-1-(E)-enyl>benzoate 
• 133043-09-1 (+)-(S)-dimethylzearalenone trimethylene dithioketal 
• 16320-11-9 (S)-(-)-zearalenone dimethyl ether ethylene glycol 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 
• 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 
• 130625-83-1 (2S)-5-(Dithian-2-yl)pentan-2-yl 2,4-dimethoxy-6-(E-prop-1-enyl)benzoate 

Downstream Products

• 30648-92-1 2,4-Dimethoxy-6--benzoesaeure 
• 17924-92-4 zearalenone 
• 17194-80-8 Zearalenone Dimethyl Ether 
• 17851-58-0 2-{(E)-5-[2-(4-Hydroxy-pentyl)-[1,3]dioxolan-2-yl]-pent-1-enyl}-4,6-dimethoxy-benzoic acid 
• 78773-31-6 1-(3,5-dimethoxy-6-carboxyphenyl)-10-methylsulfonate-1-undecene 6-ethylene ketal 
• 31749-60-7 2-<10-Hydroxy-6-oxo-undecen-(1)-yl>-4,6-dimethoxy-benzoesaeure 

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.

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

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.