115825-61-1

Basic information

• Product Name: (3beta,7alpha)-3,7,15-trihydroxy-12,13-epoxytrichothec-9-en-8-one
• Synonyms: (3alpha,7alpha)-3,7,15-Trihydroxy-12,13-epoxytrichothec-9-en-8-one; 4-Deoxynivalenol; 4-Desoxynivalenol; Deoxynivalenol; Desoxynivalenol; Trichothec-9-en-8-one, 12,13-epoxy-3,7,15-trihydroxy-, (3.alpha.,7.alpha.)-; Trichothec-9-en-8-one, 12,13-epoxy-3,7,15-trihydroxy-, (3alpha,7alpha)-; Vomitoxin
• CAS NO: 115825-61-1
• Molecular Formula: C₁₅H₂₀O₆
• Molecular Weight: 296.3157
• Mol File: 115825-61-1.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 543.9°C at 760 mmHg
• Flash Point: 206.9°C
• Density: 1.48g/cm³
• Vapor Pressure: 4.26E-14mmHg at 25°C
• Refractive Index: 1.632
• CAS DataBase Reference: (3beta,7alpha)-3,7,15-trihydroxy-12,13-epoxytrichothec-9-en-8-one(CAS DataBase Reference)
• NIST Chemistry Reference: (3beta,7alpha)-3,7,15-trihydroxy-12,13-epoxytrichothec-9-en-8-one(115825-61-1)
• EPA Substance Registry System: (3beta,7alpha)-3,7,15-trihydroxy-12,13-epoxytrichothec-9-en-8-one(115825-61-1)

Safety Data

• Hazardous Substances Data: 115825-61-1(Hazardous Substances Data)

Upstream product

• 50722-38-8 3-acetoxy-7,15-dihydroxy-12,13-epoxytrichothec-9-en-8-one 
• 115825-62-2 3-O-acetyl-4-deoxynivalenol 
• 88337-96-6 15-acetoxy-3,7-dihydroxy-12,13-epoxytrichothec-9-en-8-one 
• 50722-38-8 3α-acetoxy-7α,15-dihydroxy-12,13-epoxytrichothec-9-en-8-one 
• 119649-05-7 deoxynivalenol tristrimethylsilyl ether 
• 119649-05-7 tris(trimethylsilyl)ether of deoxynivalenol 

Downstream Products

• 88337-96-6 15-acetoxy-3,7-dihydroxy-12,13-epoxytrichothec-9-en-8-one 
• 56676-60-9 3,15-diacetyldeoxynivalenol 

Relevant articles and documents

Sulfation of deoxynivalenol, its acetylated derivatives, and T2-toxin

The synthesis of several sulfates of trichothecene mycotoxins is presented. Deoxynivalenol (DON) and its acetylated derivatives were synthesized from 3-acetyldeoxynivalenol (3ADON) and used as substrate for sulfation in order to reach a series of five different DON-based sulfates as well as T2-toxin-3-sulfate. These substances are suspected to be formed during phase-II metabolism in plants and humans. The sulfation was performed using a sulfuryl imidazolium salt, which was synthesized prior to use. All protected intermediates and final products were characterized via NMR and will serve as reference materials for further investigations in the fields of toxicology and bioanalytics of mycotoxins.

Structure-activity relationships of trichothecene toxins in an Arabidopsis thaliana leaf assay

Many Fusarium species produce trichothecenes, sesquiterpene epoxides that differ in patterns of oxygenation and esterification at carbon positions C-3, C-4, C-7, C-8, and C-15. For the first comprehensive and quantitative comparison of the effects of oxygenation and esterification on trichothecene phytotoxicity, we tested 24 precursors, intermediates, and end products of the trichothecene biosynthetic pathway in an Arabidopsis thaliana detached leaf assay. At 100 μM, the highest concentration tested, only the trichothecene precursor trichodiene was nontoxic. Among trichothecenes, toxicity varied more than 200-fold. Oxygenation at C-4, C-8, C-7/8, or C-15 was, on average, as likely to decrease as to increase toxicity. Esterification at C-4, C-8, or C-15 generally increased toxicity. Esterification at C-3 increased toxicity in one case and decreased toxicity in three of eight cases tested. Thus, the increase in structural complexity along the trichothecene biosynthetic pathway in Fusarium is not necessarily associated with an increase in phytotoxicity.

Preparation of 10-g Quantities of 15-O-Acetyl-4-deoxynivalenol

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