DEOXYNIVALENOL Chemical Properties

Melting point:

151-153 C

alpha 

D25+6.35° (c = 0.07 in ethanol)

Boiling point:

357.92°C (rough estimate)

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

form 

solution (ethanol: 2-propanol 95:5)

pka

11.91±0.70(Predicted)

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

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|

LogP

-1.250 (est)

CAS DataBase Reference

51481-10-8

Safety Information

Hazard Codes 

T,Xn,F,Xi

Risk 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

RIDADR 

UN 2811 6.1/PG 2

WGK Germany 

3

RTECS 

YD0167000

HazardClass 

6.1(a)

PackingGroup 

I

HS Code 

29329990

Hazardous Substances Data

51481-10-8(Hazardous Substances Data)

Toxicity

LD50 i.p. in male, female mice (mg/kg): 70.0, 76.7 (Yoshizawa, Morooka)

MSDS

• Language:English Provider:SigmaAldrich

DEOXYNIVALENOL Usage And Synthesis

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

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.

Uses

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.

Uses

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.

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

DEOXYNIVALENOL(51481-10-8)Related Product Information

• Atropine
• T-2 TOXIN
• DEOXYNIVALENOL
• 15-ACETOXY-3ALPHA,7ALPHA-DIHYDROXY-12,13-EPOXYTRICHOTHEC-9-EN-8-ONE
• 3-ACETYL-DEOXYNIVALENOL SOLUTION (100&MU
• DEOXYNIVALENOL-3-GLUCOSIDE
• NIVALENOL
• DEOXYNIVALENOL-13C15,FULLY 13C-LABELLED DEOXYNIVALENOL
• Deepoxy-deoxynivalenol solution
• DEOXYNIVALENOL 1X1ML ETOAC/MEOH(95:5)
• DEOXYNIVALENOL-D1,Deoxynivalenol-d1 solution
• 15-Acetylvomitoxin, 3-d3-AcDON
• Maize flour (deoxynivalenol, blank)
• 13C15 DON, Fully 13C-labelled Deoxynivalenol,Deoxynivalenol-13C15 solution
• Deoxynivalenol in Maize Flour
• WHEAT FLOUR - DEOXYNIVALENOL (DON)(BLANK)(CRM STANDARD)
• MAIZE FLOUR - DEOXYNIVALENOL (DON)(MEDIUM LEVEL)(CRM STANDARD)
• MAIZE FLOUR - DEOXYNIVALENOL (DON)(BLANK)(CRM STANDARD)