51550-28-8

Basic information

• Product Name: (3beta,7alpha)-8-oxo-12,13-epoxytrichothec-9-ene-3,7,15-triyl triacetate
• CAS NO: 51550-28-8
• Molecular Formula: C₂₁H₂₆O₉
• Molecular Weight: 422.4257
• Mol File: 51550-28-8.mol

Chemical Properties

• Boiling Point: 520.8°C at 760 mmHg
• Flash Point: 225.9°C
• Density: 1.34g/cm³
• Vapor Pressure: 6E-11mmHg at 25°C
• Refractive Index: 1.55
• CAS DataBase Reference: (3beta,7alpha)-8-oxo-12,13-epoxytrichothec-9-ene-3,7,15-triyl triacetate(CAS DataBase Reference)
• NIST Chemistry Reference: (3beta,7alpha)-8-oxo-12,13-epoxytrichothec-9-ene-3,7,15-triyl triacetate(51550-28-8)
• EPA Substance Registry System: (3beta,7alpha)-8-oxo-12,13-epoxytrichothec-9-ene-3,7,15-triyl triacetate(51550-28-8)

Safety Data

• Hazardous Substances Data: 51550-28-8(Hazardous Substances Data)

Usage

Uses

Due to the provided materials not specifying any particular applications for (3beta,7alpha)-8-oxo-12,13-epoxytrichothec-9-ene-3,7,15-triyl triacetate, it is not possible to list its uses as was done for Glycerol in the example. However, given its potential biological activity and the fact that it belongs to the trichothecene family, it could potentially be studied for applications in areas such as:
Used in Pharmaceutical Research:
(3beta,7alpha)-8-oxo-12,13-epoxytrichothec-9-ene-3,7,15-triyl triacetate could be used as a research compound for investigating its interaction with cellular processes and enzymes, which may lead to the development of new pharmaceutical agents or a better understanding of its toxicological profile.
Used in Toxicological Studies:
Understanding the toxicity and mechanism of action of (3beta,7alpha)-8-oxo-12,13-epoxytrichothec-9-ene-3,7,15-triyl triacetate could be crucial for toxicological studies, potentially informing the development of antidotes or preventive measures against exposure to similar mycotoxins.

Upstream product

• 108-24-7 acetic anhydride 
• 51481-10-8 vomitoxin hydrate 
• 50722-38-8 3-acetoxy-7,15-dihydroxy-12,13-epoxytrichothec-9-en-8-one 
• 119649-05-7 deoxynivalenol tristrimethylsilyl ether 

Downstream Products

• 54996-64-4 7-acetyl-4-deoxynivalenol 
• 54996-63-3 7,15-diacetoxy-4-deoxynivalenol 
• 88054-24-4 de-epoxy-deoxynivalenol 

Relevant articles and documents

Chemical Deoxygenation of the Trichothecenes Diacetoxyscirpenol and Deoxynivalenol

Based on a model study using the bicyclooctane epoxy acetates (14) and (15), an efficient one-step procedure for the selective removal of the 12,13-epoxide ring of the trichothecene mycotoxins diacetoxyscirpenol (1; R=H) and deoxynivalenol (2; R=H) has been devised.The key to success proved to be use of the lower-valent tungsten deoxygenation system of Sharpless et al.

Trichothecene mycotoxin interconversions: Partial syntheses of calonectrin and deoxynivalenol, and of a trichothecene epi-epoxide, 3α,4β,15-triacetoxy-12,13-epi-epoxytrichothec-9-ene

The partial syntheses of two trichothecenes, calonectrin (4β,15-diacetoxy-12,13-epoxytrichothec-9-ene) and deoxynivalenol (3α,7α,15-trihydroxy-12,13-epoxytrichothec-9-ene), from a readily available trichothecene, anguidine (4β,15-diacetoxy-3α-hydroxy-12,13-epoxytrichothec-9-ene) are described. In addition, and in order to provide further insight into the mode of action of the trichothecene mycotoxins, 3α,4β,15-tricetoxy-12,13-epi-epoxytrichothec-9-ene, of the first semisynthetic trichothecene epi-epoxides, has been prepared and its X-ray crystal structure determined. In significant contrast to its natural isomer, epi-epoxide proved to be biologically inactive.

Chemical Deoxygenation of the Trichothecenes, Diacetoxyscirpenol and Deoxynivalenol

Based on a model study using the bicyclic epoxides (9) and (10), an efficient one-step procedure for the selective removal of the 12,13-epoxide ring of the trichothecene toxins has been devised.

Chemical deoxygenation of the epoxide moiety in deoxynivalenol (vomitoxin)

Reaction of triacetoxydeoxynivalenol (3) with hydrobromic acid - acetic acid at reflux temperatures yielded 3α,7α,13,15-tetraacetoxy-2-bromo apotrichothec-9-en-8-one (5) and 3α,7α,15-triacetoxy-13-bromo-12-hydroxytrichothec-9-en-8-one (4).Dehalohydrination of the 13,12-bromohydrin derivative with Zn - acetic acid followed by deacetylation with sodium ethoxide gave 3α,7α,15-trihydroxytrichothec-9,12-dien-8-one (2).This compound proved identical to the transformation product isolated from incubation of deoxynivalenol (vomitoxin) in vitro with rumen microorganisms.

Phytotoxic Compounds Produced by Fusarium equiseti. Part 7. Reactions and Rearrangement of the 7-Hydroxy-12,13-epoxytrichothec-9-en-8-one Skeleton

7α,15-Dihydroxy-12,13-epoxytrichothec-9-en-8-ones, e.g. nivalenol and vomitoxin, rearrange under mild basic conditions to the isomeric 7,13-epoxy-A-nortrichothecane-7-carboxylic acid 15-lactones.With hydrogen chloride, normal addition to the 12,13-epoxide of these compounds occurs, with retention of configuration at C-12, and the more usual rearrangement to the 2β-chloroaprotrichothec-9-en-8-one skeleton is not seen.Catalytic hydrogenation of diacetylnivalenol takes place from the β-face to give correspoding (9R)-trichothecan-8-one.Reliable procedures for the preparation of vomotoxin and nivalenol from their acetates are outlined.