3-Acetyl-deoxynivalenol

Name: 3-Acetyl-deoxynivalenol
SKU: D1760
Availability: InStock

Product ID D1760

Cas No. 50722-38-8

Purity ≥98%

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Description

3-acetyl deoxynivalenol (3-A-DON) a type A trichothecene mycotoxin initially produced by species of Fusarium. 3-A-DON is typically found in grains used for livestock feed as well as human consumption, such as cereal and bread. This compound exhibits potential anticancer and immunomodulatory benefit in vitro, upregulating IL-8 production and inducing apoptosis in Jurkat T cells. 3-A-DON also displays biphasic effects on cytokine production in CD4+ T cells, initially decreasing expression of IL-2, IL-4, and IL-5, then increasing expression of all three after 7 days of exposure. 3-A-DON also inhibits the plaque-forming cell response and decreases total lymphocyte numbers in vitro.

Product Info

Cas No.	50722-38-8
Purity	≥98%
Formula	C₁₇H₂₂O₇
Formula Wt.	338.35
Chemical Name	[(1R,2R,3S,7R,9R,10R,12S)-3-hydroxy-2-(hydroxymethyl)-1,5-dimethyl-4-oxospiro[8-oxatricyclo[7.2.1.02,7]dodec-5-ene-12,2'-oxirane]-10-yl] acetate
IUPAC Name	[(1R,2R,3S,7R,9R,10R,12S)-3-hydroxy-2-(hydroxymethyl)-1,5-dimethyl-4-oxospiro[8-oxatricyclo[7.2.1.02,7]dodec-5-ene-12,2'-oxirane]-10-yl] acetate
Synonym	3-Acetyl-Deoxynivalenol 3α-Acetylvomitoxin 3-Acetyl don 3-Acetyldeoxynivalenol Dehydronivalenol monoacetate Deoxynivalenol monoacetate NSC 26703
Melting Point	185-187°C
Solubility	Soluble in acetonitrile, methanol (10 mg/mL) and ethyl acetate (10 mg/mL), only slightly soluble in water.
Appearance	White crystalline solid

Shipping and Storage

Store Temp	4°C
Ship Temp	Ambient

Downloads

MSDS	D1760 MSDS PDF
Info Sheet	D1760 Info Sheet PDF

References

Puri KD, Zhong S. The 3ADON population of Fusarium graminearum found in North Dakota is more aggressive and produces a higher level of DON than the prevalent 15ADON population in spring wheat. Phytopathology. 2010 Oct;100(10):1007-14. PMID: 20839936.

Monbaliu S, Van Poucke C, Detavernier C, et al. Occurrence of mycotoxins in feed as analyzed by a multi-mycotoxin LC-MS/MS method. J Agric Food Chem. 2010 Jan 13;58(1):66-71. PMID: 19994896.

Gottschalk C, Barthel J, Engelhardt G, et al. Occurrence of type A trichothecenes in conventionally and organically produced oats and oat products. Mol Nutr Food Res. 2007 Dec;51(12):1547-53. PMID: 18030660.

Pestka JJ, Uzarski RL, Islam Z. Induction of apoptosis and cytokine production in the Jurkat human T cells by deoxynivalenol: role of mitogen-activated protein kinases and comparison to other 8-ketotrichothecenes. Toxicology. 2005 Jan 15;206(2):207-19. PMID: 15588914.

Ouyang YL, Azcona-Olivera JI, Pestka JJ. Effects of trichothecene structure on cytokine secretion and gene expression in murine CD4+ T-cells. Toxicology. 1995 Dec 15;104(1-3):187-202. PMID: 8560498.

Tomar RS, Blakley BR, Schiefer HB, et al. In vitro effects of 3-acetyl-deoxynivalenol on the immune response of human peripheral blood lymphocytes. Int J Immunopharmacol. 1986;8(2):125-30. PMID: 3710661.