Deoxynivalenol

Base Information

• Chemical Name: Deoxynivalenol
• CAS No.: 51481-10-8
• Deprecated CAS: 50722-37-7,115825-61-1
• Molecular Formula: C15H20 O6
• Molecular Weight: 296.32
• Hs Code.: 29329990
• European Community (EC) Number: 610-668-0
• UNII: JT37HYP23V
• DSSTox Substance ID: DTXSID3020382
• Nikkaji Number: J3.819I
• Wikipedia: Vomitoxin
• Wikidata: Q420518
• Metabolomics Workbench ID: 141174
• ChEMBL ID: CHEMBL513300
• Mol file: 51481-10-8.mol

Synonyms:3-epi-deoxynivalenol;3-epi-DON;deoxynivalenol;vomitoxin

Chemical Property of Deoxynivalenol

Chemical Property:

• Vapor Pressure: 4.26E-14mmHg at 25°C
• Melting Point: 151-153 C
• Refractive Index: 1.4359 (estimate)
• Boiling Point: 543.9°Cat760mmHg
• PKA: 11.91±0.70(Predicted)
• Flash Point: 206.9°C
• PSA: 99.52000
• Density: 1.48g/cm³
• LogP: -0.83770
• Storage Temp.: 2-8°C
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 1
• Exact Mass: 296.12598835
• Heavy Atom Count: 21
• Complexity: 558

Purity/Quality:

99% ^*data from raw suppliers

Deoxynivalenol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,Xn,F,Xi
• Hazard Codes: T,Xn,F,Xi
• Statements: 25-68/20/21/22-67-66-36-20/21/22-11-36/37/38
• Safety Statements: 36/37/39-45-36-26-16-36/37-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Mycotoxins
• Canonical SMILES: CC1=CC2C(C(C1=O)O)(C3(CC(C(C34CO4)O2)O)C)CO
• Isomeric SMILES: CC1=C[C@@H]2[C@]([C@@H](C1=O)O)([C@]3(C[C@H]([C@H]([C@@]34CO4)O2)O)C)CO
• Description: Vomitoxin or deoxynivalenol (DON) is one of the trichothecenes (mycotoxins) which comprise a large group (148 or more have been identified) of protein synthesis inhibitors. These mycotoxins are also powerful immunosuppressants which may predispose animals to other diseases. Vomitoxin is the most commonly found trichothecene in moldy corn (maize), but a number of other biologically active trichothecenes are produced by species of the fungus Fusarium. These include nivalenol, T-2 toxin, HT-2 toxin, diacetoxyscirpenol (DAS), and monoacetoxyscipenol (MAS). These mycotoxins are most toxic when fed to swine and other monogastric animals including humans. Poultry are generally more resistant to trichothecenes than hogs, whereas T-2 toxin and DAS appear to be more toxic to chickens than vomitoxin. Toxins already present in corn at harvest may increase in stored ear corn. Extended periods of warm, rainy, or damp weather from flowering time onward promote infection of corn by Fusarium species (1–7). 4-deoxy Nivalenol is a trichothecene mycotoxin that has been found in Fusarium. It binds to eukaryotic ribosomes and inhibits protein synthesis in mice when administered at doses ranging from 5 to 25 mg/kg. 4-deoxy Nivalenol (0.1 and 0.2 mg/kg) induces emesis in pigs and decreases feed consumption in pigs when administered at a dose of 40 ppb in the diet. It induces lethality in mice (LD50 = 46-78 mg/kg). 4-deoxy Nivalenol has been found in F. graminearum-infected cereal grains such as wheat, barley, and corn.
• Uses: Deoxynivalenol is a natural type B trichothecene produced by certain species of the fungus Fusarium, particularly those found on cereal crops, including wheat, barley, oats, maize, and rye. This mycotoxin can induce vomiting, diarrhea, and weight loss as well as other physiological and toxicological effects. It inhibits protein biosynthesis, binds to peptidyl transferase, and inhibits the synthesis of RNA and DNA, contributing to immunotoxicity. It passes the blood-brain barrier at different rates in different animals and this may be related to anorexia. Deoxynivalenol solution has been used as an analytical reference standard for the quantification of the analyte in cornmeal and wheat meal matrices using high-performance liquid chromatography with UV detection (HPLC-UV). It is used as an analytical standard in investigating its toxicity mechanism on human chondrocytes by microarray and bioinformatics analysis. Deoxynivalenol is a tricothecene mycotoxin and potent protein synthesis inhibitor. Deoxynivalenol exhibits cytotoxic activity in vivo via the ribotoxic stress response. Deoxynivalenol induces p38-mediated gene expression and apoptosis in leukocytes; activity results in systemic expression of interleukin-6 (IL-6) and other proinflammatory cytokines. Also induces migration of NF-κB into the nucleus.

Technology Process of Deoxynivalenol

There total 7 articles about Deoxynivalenol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

deoxynivalenol tristrimethylsilyl ether (119649-05-7) → vomitoxin hydrate (51481-10-8,50722-37-7,115825-61-1)

Guidance literature:

With hydrogen fluoride; In water; acetonitrile; for 0.5h;

Reference yield: 94.0%

3-O-acetyl-4-deoxynivalenol (115825-62-2) → vomitoxin (51481-10-8,50722-37-7,115825-61-1)

Guidance literature:

With sodium methylate; In methanol; for 2h; Inert atmosphere;

DOI:10.1016/j.tet.2014.05.064

Reference yield: 82.0%

3α-acetoxy-7α,15-dihydroxy-12,13-epoxytrichothec-9-en-8-one (50722-38-8,115825-62-2) → vomitoxin hydrate (51481-10-8,50722-37-7,115825-61-1)

Guidance literature:

With ammonium hydroxide; In methanol; for 6h; Ambient temperature;

DOI:10.1021/jo00251a040

upstream raw materials:

3-acetoxy-7,15-dihydroxy-12,13-epoxytrichothec-9-en-8-one

tris(trimethylsilyl)ether of deoxynivalenol

deoxynivalenol tristrimethylsilyl ether

3α-acetoxy-7α,15-dihydroxy-12,13-epoxytrichothec-9-en-8-one

Downstream raw materials:

de-epoxy-deoxynivalenol

Deoxynivalenol triacetate

15-acetoxy-3,7-dihydroxy-12,13-epoxytrichothec-9-en-8-one

3,15-diacetyldeoxynivalenol

Refernces

• 1、 Fruhmann, Philipp,Skrinjar, Philipp,Weber, Julia,Mikula, Hannes,Warth, Benedikt,Sulyok, Michael,Krska, Rudolf,Adam, Gerhard,Rosenberg, Erwin,Hametner, Christian,Fr?hlich, Johannes. "Sulfation of deoxynivalenol, its acetylated derivatives, and T2-toxin". . p. 5260 - 5266. Retrieved 2014/12/10.
• 2、 Cameron,Colvin. "Trichothecene mycotoxin interconversions: Partial syntheses of calonectrin and deoxynivalenol, and of a trichothecene epi-epoxide, 3α,4β,15-triacetoxy-12,13-epi-epoxytrichothec-9-ene". . p. 887 - 895. Retrieved 2007/10/02.