The origin of naturally-occurring acetylenes

Abstract

The hypothesis that the triple bond of natural acetylenes is formed by a dehydrogenation and that these compounds are derived from common fatty acids by various oxidation processes is confirmed by the demonstration that [10-¹⁴C]oleic acid is converted by Tricholoma grammopodium into [10-¹⁴C]octadec-9-en-12-ynoic acid and into [2-¹⁴C]dec-2-en-4,6,8-triyn-1-ol, and by the presence in polyacetylene-producing fungi of two of the postulated intermediates, cis-octadec-9-en-12-ynoic (crepenynic) and cis,cis-octadec-9,14-dien-12-ynoic (dehydrocrepenynic) acids.