9650. Trichothecin

Nomenclature

CAS number: 6379-69-7
[4β(Z)]-12,13-Epoxy-4-[(1-oxo-2-butenyl)oxy]trichothec-9-en-8-one; 12,13-epoxy-4-hydroxytrichothec-9-en-8-one crotonate.
C19H24O5; mol wt 332.39.
C 68.66%, H 7.28%, O 24.07%.

Description and references

Mycotoxin with antibiotic activity. Produced by Trichothecium roseum: Freeman, Morrison, Nature 162, 30 (1948). Activity: G. G. Freeman, J. Gen. Microbiol. 12, 213 (1955). Structure: Godtfredsen, Vangedal, Proc. Chem. Soc. London 1964, 188; Gutzwiller et al., Helv. Chim. Acta 47, 2234 (1964). Biogenesis: Jones, Lowe, J. Chem. Soc. 1960, 3959. Biosynthetic studies: Achilladelis et al., J. Chem. Soc. Perkin Trans. 1 1972, 1425; Machida, Nozoe, Tetrahedron Lett. 1972, 1969; eidem, Tetrahedron 28, 5113 (1972).

Chemical structure

Properties

Slender needles from petrol ether, mp 118°. [α]D18 +44° (c = 1 in CHCl3). uv max (hexane): 217 nm (ε 18000); (methanol): 215 nm (ε 19000). Slightly sol in water (400 mg/l at 25°). Freely sol in most organic solvents. Aq solns are stable at pH 1-10 for at least 48 hrs at 20°. At pH 12 the antifungal activity is destroyed rapidly. Aq solns at pH 7 can be maintained at 100° for at least one hour without loss of activity. LD50 i.v. in mice: ≈300 mg/kg (Freeman).