103776-39-2

Basic information

• Product Name: (2R,3R,3aR,8bR)-3a-(hydroxymethyl)-6,8b-dimethyl-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-2,3,5-triol
• Synonyms: 1H-Cyclopenta[b]benzofuran-2,3,5-triol, 1,2,3,8b-tetrahydro-3a-(hydroxymethyl)-6,8b-dimethyl-, (2R,3R,3aR,8bR)-
• CAS NO: 103776-39-2
• Molecular Formula: C₁₄H₁₈O₅
• Molecular Weight: 266.2897
• Mol File: 103776-39-2.mol

Chemical Properties

• Boiling Point: 453°C at 760 mmHg
• Flash Point: 227.8°C
• Density: 1.474g/cm³
• Vapor Pressure: 5.36E-09mmHg at 25°C
• Refractive Index: 1.676
• CAS DataBase Reference: (2R,3R,3aR,8bR)-3a-(hydroxymethyl)-6,8b-dimethyl-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-2,3,5-triol(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3R,3aR,8bR)-3a-(hydroxymethyl)-6,8b-dimethyl-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-2,3,5-triol(103776-39-2)
• EPA Substance Registry System: (2R,3R,3aR,8bR)-3a-(hydroxymethyl)-6,8b-dimethyl-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-2,3,5-triol(103776-39-2)

Safety Data

• Hazardous Substances Data: 103776-39-2(Hazardous Substances Data)

Upstream product

• 51481-10-8 vomitoxin hydrate 
• 115825-62-2 3-O-acetyl-4-deoxynivalenol 

Relevant articles and documents

Thermal degradation of the Fusarium mycotoxin deoxynivalenol

Deoxynivalenol (DON) is a toxic secondary metabolite produced by molds of the Fusarium genus, which are able to infect cereal crops in the field. Concerning its rate of occurrence and mean concentration, DON is one of the most important mycotoxins in cereal commodities. Its toxic effects range from causing diarrhea, vomiting, and gastro-intestinal inflammation to noncompetitive inhibition of the biosynthesis of proteins in eukaryotic cells. To study the stability of DON under food-processing conditions such as cooking or baking, we performed model heating experiments and screened the residue for degradation products. Heating of DON and 3-acetyldeoxynivalenol (3-AcDON), especially under alkaline conditions, gave a mixture of compounds, which were isolated and structurally elucidated by NMR and MS experiments. Three of these compounds were already known (norDON A, norDON B, and norDON C), while four were new and named 9-hydroxymethyl DON lactone, norDON D, norDON E, and norDON F. The significance of the DON degradation products was checked by analyzing commercially available food samples. norDON A, B, and C were detected in 29-66% of the samples in mean concentrations ranging from 3 to 15 μg/kg. Furthermore, cell culture experiments using IHKE cells showed that the compounds that were detected in food samples are less cytotoxic in the formazan dye cytotoxicity assay compared to DON. Whereas DON revealed a median effective concentration (EC50) at 1.1 μmol/L, all other compounds did not show any significant effect up to 100 μmol/L. These findings indicate that the degradation of DON under thermal treatment might reduce the toxicity of DON contaminated food.

ALKALINE DEGRADATION OF THE MYCOTOXIN 4-DEOXYNIVALENOL

Treatment of the Fusarium trichothecene mycotoxin 4-deoxynivalenol (1) (DON) with aqueous NaOH at 75 deg C gave a mixture of three isomeric degradation products designated norDON-A (3a), norDON-B (4a) and norDON-C (5a).Structures and a mechanism for the formation of these products are proposed.