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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

Certificats d'analyse (COA)

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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)
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)
Michael Bretz et al.
Molecular nutrition & food research, 50(3), 251-260 (2006-03-08)
Trichothecenes are secondary metabolites produced by several fungi of the Fusarium genus during their growth period. They inhibit protein biosynthesis in eukaryotic cells resulting in numerous toxic effects such as diarrhea, vomiting, and gastro-intestinal inflammation. Considering its occurrence in food
Rie Tsuyuki et al.
Journal of agricultural and food chemistry, 59(5), 1760-1766 (2011-02-09)
The effects of cobalt chloride on the production of trichothecene and ergosterol in Fusarium graminearum were examined. Incorporation experiments with (13)C-labeled acetate and leucine confirmed that both 3-acetyldeoxynivalenol and ergosterol were biosynthesized via a mevalonate pathway by the fungus, although
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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