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HomeProduct name listDEOXYNIVALENOL

DEOXYNIVALENOL

Synonym(s):DON;Vomitoxin;DON solution;RD-toxon;(3α,7α)-3,7,15-trihydroxy-12,13-epoxytrichothec-9-en-8-one

  • CAS NO.:51481-10-8
  • Empirical Formula: C15H20O6
  • Molecular Weight: 296.32
  • MDL number: MFCD09039270
  • EINECS: 610-668-0
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-07-02 08:54:58
DEOXYNIVALENOL Structural

What is DEOXYNIVALENOL?

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).

Description

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.

Chemical properties

Off-White Solid

The Uses of DEOXYNIVALENOL

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.

The Uses of DEOXYNIVALENOL

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.

The Uses of DEOXYNIVALENOL

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.

What are the applications of Application

Deoxynivalenol is Deoxynivalenol is a Fusarium mycotoxin, known for immunosuppressive characteristics and gene deregulation.

Definition

ChEBI: Deoxynivalenol is a trichothecene mycotoxin produced by Fusarium to which wheat, barley, maize (corn) and their products are susceptible to contamination. It has a role as a mycotoxin. It is a trichothecene, a cyclic ketone, a secondary alpha-hydroxy ketone, a primary alcohol, an enone and a triol.

General Description

Deoxynivalenol belongs to the class of type B trichothecene mycotoxins typically produced by the species of Fusarium genus. It is cytotoxic and is known to hinder the macromolecular synthesis.

Biochem/physiol Actions

Deoxynivalenol (DON) is a trichothecene mycotoxin that inhibits the synthesis of DNA and RNA as well as protein synthesis at the ribosomal level. DON induces IL-6 mediated serum hyperelevation of IgA, as well as phosphorylation of extracellular signal regulated protein kinases 1 and 2 (ERK 1,2) and c-Jun N-terminal kinases 1 and 2 (JNK 1,2) in mice. An in vitro study with porcine ovarian granulosa cells suggests a dose dependent association of DON on porcine ovarian functions. It was also shown that LPS and its downstream mediators can interact with DON to modulate proliferative, cytotoxic and apoptotic outcomes in leukocytes in a tissue specific manner.

storage

Store at +4°C

Properties of DEOXYNIVALENOL

Melting point: 151-153 C
Boiling point: 357.92°C (rough estimate)
alpha  D25+6.35° (c = 0.07 in ethanol)
Density  1.48
refractive index  1.4359 (estimate)
Flash point: -3 °C
storage temp.  -20°C
solubility  DMF: 30 mg/ml; DMSO: 25 mg/ml; Ethanol: 30 mg/ml; PBS (pH 7.2): 10 mg/ml
pka 11.91±0.70(Predicted)
form  solution (ethanol: 2-propanol 95:5)
color  White to off-white
Merck  13,10092
Stability: Stable. Incompatible with strong oxidizing agents.
InChI InChI=1/C15H20O6/c1-7-3-9-14(5-16,11(19)10(7)18)13(2)4-8(17)12(21-9)15(13)6-20-15/h3,8-9,11-12,16-17,19H,4-6H2,1-2H3/t8-,9-,11-,12-,13-,14-,15+/s3
CAS DataBase Reference 51481-10-8

Safety information for DEOXYNIVALENOL

Signal word Danger
Pictogram(s)
ghs
Flame
Flammables
GHS02
ghs
Exclamation Mark
Irritant
GHS07
ghs
Health Hazard
GHS08
GHS Hazard Statements H225:Flammable liquids
H319:Serious eye damage/eye irritation
H336:Specific target organ toxicity,single exposure; Narcotic effects
H371:Specific target organ toxicity, single exposure
Precautionary Statement Codes P210:Keep away from heat/sparks/open flames/hot surfaces. — No smoking.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for DEOXYNIVALENOL

InChIKey LINOMUASTDIRTM-QUKTVYMZNA-N
SMILES [C@@]12(CO1)[C@@]1([H])[C@H](O)C[C@]2(C)[C@@]2(CO)[C@H](O)C(C(C)=C[C@@]2([H])O1)=O |&1:0,3,5,8,10,13,19,r|

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