Biotransformation of saturated monohydroxyl fatty acids to 2-tetrahydrofuranyl acetic acid derivatives: Mechanism of formations and the biological activity of 5-n-hexyl-tetrahydrofuran-2-acetic acid

Article abstract of DOI:10.1007/BF02523511

The transformation of 12-hydroxyoctadecanoic acid (12-HOA) to 5-n-hexyl-tetrahydofuran-2-acetic acid (5-HTFA) by Bacillus lentus NRRL B-14864 was carried out in the presence and absence of oligomycin, 2-bromooctanoic acid (2-BA), or sodium azide. Methyl esters of the transformation products were analyzed by gas chromatography and gas chromatography/mass spectroscopy. Results suggest that the production of 5-HTFA from 12-HOA by B-14864 was through the fatty acid beta-oxidation pathway. Three-day old driedfruit beetle pupae were topically treated with 5-HTFA to test for juvenile hormone activity, and 5-HTFA was found to possess juvenile hormone-like activity in pure form but not when it was diluted to 10 percent.