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D0156

Sigma-Aldrich

Deoxynivalenol

Synonym(s):

3α,7α,15-Trihydroxy-12,13-epoxytrichothec-9-en-8-one, Vomitoxin

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About This Item

Empirical Formula (Hill Notation):
C15H20O6
CAS Number:
51481-10-8
Molecular Weight:
296.32
MDL number:
MFCD09039270
UNSPSC Code:
12352200
PubChem Substance ID:
24893213
NACRES:
NA.77

form

powder

Quality Level

300

storage temp.

2-8°C

SMILES string

[H][C@]12O[C@]3([H])[C@H](O)C[C@@](C)([C@]34CO4)[C@@]1(CO)[C@H](O)C(=O)C(C)=C2

InChI

1S/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+/m1/s1

InChI key

LINOMUASTDIRTM-QGRHZQQGSA-N

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General description

Deoxynivalenol (DON) is a natural mycotoxin found in Fusarium graminearum and Fusarium culmorum. It belongs to the B-trichothecenes family of mycotoxins.

Application

Deoxynivalenol has been used:

  • as a mycotoxin to induce cytotoxicity in porcine jejunal epithelial cells and study the protective effects of Saccharomyces cerevisiae on the cell viability of host cells.
  • to induce toxicity in nude mice to study the effect of probiotics (Lactobacillus rhamnosus GG (LGG) or Lactobacillus acidophilus (LA)) supplementation on host protection
  • as a thyroid hormone receptor (TRβ) antagonist in cell-based luciferase reporter gene (CALUX) assay

Biochem/physiol Actions

Deoxynivalenol (DON) blocks the synthesis of DNA and RNA by inhibiting the process of translation.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H300

Hazard Classifications

Acute Tox. 2 Oral

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Deepoxy-deoxynivalenol solution ~50 μg/mL in acetonitrile, analytical standard

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Yang Liu et al.
AMB Express, 9(1), 137-137 (2019-09-05)
Deoxynivalenol (DON) is one of the mycotoxins most frequently encountering in cereal-based foods throughout the world. Saccharomyces cerevisiae was used to alleviate porcine jejunal epithelia cell (IPEC-J2) injury induced by DON in this study. The results indicated that cell viability
Toxicology of deoxynivalenol (vomitoxin).
Rotter B A.
Int J Toxicol Pharmacol Res, 48(1), 1-34 (1996)
Isabel Parraga-Aguado et al.
Journal of environmental management, 158, 74-84 (2015-05-13)
Phytomanagement in terms of phytostabilisation has been proposed as a suitable technique to decrease the environmental risks of metal(loid) enriched mine tailings. Nevertheless, at these sites some issues must be solved to assure the long-term establishment of vegetation (e.g. salinity
Miaomiao Wu et al.
PloS one, 9(7), e100591-e100591 (2014-07-02)
The mycotoxin deoxynivalenol (DON), one of the most common food contaminants, primarily targets the gastrointestinal tract to affect animal and human health. This study was conducted to examine the protective function of glutamic acid on intestinal injury and oxidative stress
Michihiro Ito et al.
Applied and environmental microbiology, 79(5), 1619-1628 (2013-01-01)
Deoxynivalenol (DON) is a natural toxin of fungi that cause Fusarium head blight disease of wheat and other small-grain cereals. DON accumulates in infected grains and promotes the spread of the infection on wheat, posing serious problems to grain production.
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