Merlin P, Braekman J C, Daloze D, Pasteels J M, Dejean A
Laboratory of Bio-Organic Chemistry, Faculty of Sciences, University of Brussels, Belgium.
Experientia. 1992 Jan 15;48(1):111-3. doi: 10.1007/BF01923621.
(6R*)-[(2S*)-2-hydroxyheneicos-12-enyl]-5,6-dihydro-2H-pyran-2-one (1) degree is the major constituent of the secretion of freshly dissected Dufour's gland of the urticating ant Tetramorium aculeatum. In solution, compound 1 is slowly transformed into (1S*,5R*,7S*)-7-(nonadec-10-enyl)-2,6-dioxabicyclo[3.3.1] nonan-3-one (2) degrees on standing. The structures of compounds 1 and 2 have been established on the basis of their spectral and chemical properties. Compound 1 could be responsible for the urticating properties of the ant.
