Biochemistry of the wood-rotting fungi. 8. Volatile metabolic products of Daedalea juniperina Murr

Abstract

The steam-volatile metabolic products of Daedalea juniperina were investigated. A new fungal metabolic product 5-([alpha]-propynyl)-2-formyl-thiophen, m.p. 80[degree], was isolated, characterized, and given the trivial name of junipal. On oxidation with the Doeuvre reagent, junipal affords junipic acid, C8H6O2S, m.p. 180[degree]. Oxidation of junipic acid with KMnO4 gives 2:5-thiophendicarboxylic acid, identified as the dimethyl ester, m.p. 145-6[degree]. The UV and infrared absorption spectra of junipal were determined and are consistent with the structure advanced. Indications of a second metabolic product closely related to junipal were obtained, and a third was identified as anisaldehyde.