10032. Vomitoxin

Nomenclature

CAS number: 51481-10-8
12,13-Epoxy-3,7,15-trihydroxytrichothec-9-en-8-one; deoxynivalenol; dehydronivalenol.
C15H20O6; mol wt 296.32.
C 60.80%, H 6.80%, O 32.40%.

Description and references

Isoln of the trichothecene mycotoxin from Fusarium roseum and structure: N. Morooka et al., J. Food Hyg. Soc. Jpn. 13, 368 (1972); T. Yoshizawa, N. Morooka, Agric. Biol. Chem. 37, 2933 (1973). Isoln from F. graminearum: R. F. Vesonder et al., Appl. Microbiol. 26, 1008 (1973); eidem, Appl. Environ. Microbiol. 31, 280 (1976). Emetic and refusal activity in swine: D. M. Forsyth et al., ibid. 34, 547 (1977). HPLC analysis: G. A. Bennett et al., J. Am. Oil Chem. Soc. 58, 1002A (1981). Implicated as a chemical warfare agent with nivalenol, q.v. in Southeast Asia: N. Wade, Science 214, 34 (1981).

Chemical structure

Properties

Fine needles from ethyl acetate + petr ether, mp 151-153°. [a]D25+6.35° (c = 0.07 in ethanol). uv max (ethanol): 218 nm (ε 4500). LD50 i.p. in male, female mice (mg/kg): 70.0, 76.7 (Yoshizawa, Morooka).