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A6166

Sigma-Aldrich

3-Acetyldeoxynivalenol from Fusarium roseum

from Fusarium roseum

Synonyme(s) :

3α-Acetoxy-7α,15-dihydroxy-12,13-epoxytrichothec-9-en-8-on, 3α-Acetylvomitoxin, 3-AcDON

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About This Item

Formule empirique (notation de Hill):
C17H22O7
Numéro CAS:
50722-38-8
Poids moléculaire :
338.35
Numéro MDL:
MFCD00135964
Code UNSPSC :
12352200
ID de substance PubChem :
24891062
Nomenclature NACRES :
NA.77

Source biologique

Fusarium roseum

Niveau de qualité

200

Forme

powder

Température de stockage

2-8°C

Chaîne SMILES 

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

InChI

1S/C17H22O7/c1-8-4-11-16(6-18,13(21)12(8)20)15(3)5-10(23-9(2)19)14(24-11)17(15)7-22-17/h4,10-11,13-14,18,21H,5-7H2,1-3H3/t10-,11-,13-,14-,15-,16-,17+/m1/s1

Clé InChI

ADFIQZBYNGPCGY-HTJQZXIKSA-N

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Description générale

3-Acetyldeoxynivalenol is a trichothecene mycotoxin, secreted by Fusarium species. It stimulates the activation of c-Jun N-terminal kinase (JNK)/ p38 mitogen-activated protein kinases and prevents protein synthesis. 3-Acetyldeoxynivalenol is a weak inducer of apoptosis.

Application

3-Acetyldeoxynivalenol has been used in a study to compare the ability of two fungi to improve wheat growth, decrease root colonization of Fusarium, and withstand mycotoxins. 3-Acetyldeoxynivalenol has also been used to induce and study anorexia in mice.

Pictogrammes

Skull and crossbones
GHS06

Mention d'avertissement

Danger

Mentions de danger

H300,H311 + H331

Classification des risques

Acute Tox. 2 Oral - Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation

Code de la classe de stockage

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

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

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

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The trichothecene biosynthesis gene cluster of Fusarium graminearum F15 contains a limited number of essential pathway genes and expressed non-essential genes
Kimura M, et al.
Febs Letters, 539(1-3), 105-110 (2003)
Trichothecene mycotoxins trigger a ribotoxic stress response that activates c-Jun N-terminal kinase and p38 mitogen-activated protein kinase and induces apoptosis
Shifrin VI and Anderson P
The Journal of Biological Chemistry, 274(20), 13985-13992 (1999)
M De Boevre et al.
Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment, 29(5), 819-835 (2012-03-01)
An LC-MS/MS method was developed and validated for the simultaneous determination of deoxynivalenol, zearalenone, T-2-toxin, HT-2-toxin and metabolites, including 3-acetyldeoxynivalenol, 15-acetyldeoxynivalenol, deoxynivalenol-3-glucoside, α-zearalenol, β-zearalenol, zearalenone-4-glucoside, α-zearalenol-4-glucoside, β-zearalenol-4-glucoside and zearalenone-4-sulfate in maize, wheat, oats, cornflakes and bread. Extraction was performed with
A Llorens et al.
International journal of food microbiology, 94(1), 43-54 (2004-06-03)
Various species of Fusarium can produce trichothecene mycotoxins that contaminate food commodities and can represent a risk for human and animal health. In this paper, a full factorial design was applied to study the influence of incubation temperature, water activity
G S Eriksen et al.
Archiv fur Tierernahrung, 57(5), 335-345 (2003-11-19)
The absorption, metabolism and excretion of 3-acetyldeoxynivalenol (3-aDON) in pigs were studied. Pigs with a faecal microflora known to be able to de-epoxidate trichothecenes were used in the experiment. The pigs were fed a commercial diet with 3-aDON added in
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