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A6166

Sigma-Aldrich

3-Acetyldeoxynivalenol

from Fusarium roseum

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C17H22O7
CAS Number:
50722-38-8
Molecular Weight:
338.35
MDL number:
MFCD00135964
UNSPSC Code:
12352200
PubChem Substance ID:
24891062
NACRES:
NA.77

biological source

Fusarium roseum

Quality Level

200

form

powder

storage temp.

2-8°C

SMILES string

[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

InChI key

ADFIQZBYNGPCGY-HTJQZXIKSA-N

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General description

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.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H300,H311 + H331

Hazard Classifications

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

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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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
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
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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