Absolute configuration of (3R,4S)-4-methyl-3-hexanol—A pheromone from the head of the ant Tetramorium impurum foerster

Abstract

The isolation of 4-methyl-3-hexanol and 4-methyl-3-hexanone from the heads of all adult castes of T. impurum (previously wrongly reported as T. caespitum is described. The important quantitative differences between the secretions of both sexes is confirmed, males producing much higher quantities of both compounds. The absolute configuration of the alcohol from the heads of males was found to be 3R,4S. In view of the sexual differences observed in T. impurum, the qualitative divergence in the secretions of T. impurum and T. caespitum is tentatively interpreted as a biochemical isolation mechanism between two sibling species.