Males of the European and African beewolf,Philanthus triangulum, possess a sex specific mandibular gland secretion that is used for marking plant stems in mating territories. The secretion is composed of 90% (Z)-11-eicosen-1-ol plus small amounts of 10-nonadecen-2-one, nonadecenal, octadecanoic and octadecenoic acids, and eicosenal. The chemistry of this secretion differs markedly from the secretions of North AmericanPhilanthus, which consist of a larger number of components that possess different chemical functionalities and are more volatile. We postulate that the chemical differences betweenP. triangulum and its New World relatives reflect phylogenetic differences plus a possible reduced necessity for species isolating mechanisms inP. triangulum.