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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

signalword

Danger

hcodes

H300

Hazard Classifications

Acute Tox. 2 Oral

Storage Class

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

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

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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Toxicology of deoxynivalenol (vomitoxin).
Rotter B A.
Int J Toxicol Pharmacol Res, 48(1), 1-34 (1996)
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
Deoxynivalenol and its toxicity
Sobrova P, et al.
Interdisciplinary Sciences, Computational Life Sciences, 3(3), 94-99 (2010)
Determination of deoxynivalenol (DON) and its derivatives: Current status of analytical methods
Ran R, et al.
Food Control, 34(1), 138-148 (2013)
Jun-Lin Song et al.
Cells, 10(8) (2021-08-28)
(1) Background: Deoxynivalenol (DON) and zearalenone (ZEA) are type B trichothecene mycotoxins that exert serious toxic effects on the reproduction of domestic animals. However, there is little information about the toxicity of mycotoxins on testis development in Equus asinus. This
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