192. Agrocybin

Nomenclature

CAS number: 544-44-5
8-Hydroxy-2,4,6-octatriynamide.
C8H5NO2; mol wt 147.13.
C 65.31%, H 3.43%, N 9.52%, O 21.75%.

Description and references

Phytotoxic acetylene responsible for killing of grass by fairy ring mushroom fungus. Isolation from basidiomycete Agrocybe dura: Kavanagh et al., Proc. Natl. Acad. Sci. USA 36, 102 (1950); from Marasmius oreades and activity: W. A. Ayer, P. A. Craw, Can. J. Chem. 67, 1371 (1989). Structure and synthesis: Bu'Lock et al., Chem. Ind. (London) 1954, 990; and spectrum: Ashworth et al., J. Chem. Soc. 1958, 950. Origin of the carbon skeleton: E. R. H. Jones et al., J. Chem. Res. Miniprint 1977, 744.

Chemical structure

Properties

Crystals from 20% alc or ether, mp 140° (conflagrates). Stable in air for about one day after which the crystals turn black and become insol in ether. Sol in alc, acetone, ether, chloroform, methyl isobutyl ketone; slightly sol in water. Practically insol in hexane.