0000000000164683
AUTHOR
Jean Claude Braekman
Synthesis of syn-4,6-dimethyldodecanal, the male sex pheromone and trail-following pheromone of two species of the termite Zootermopsis.
Recently, we reported that syn-4,6-dimethyldodecanal is the male sex pheromone and the trail-following pheromone of the Termopsidae Zootermopsis nevadensis and Zootermopsis angusticollis. In this article, we describe the syntheses of the mixture of the four stereoisomers of 4,6-dimethyldodecanal using a synthetic pathway where the key step is a Wittig reaction between methyl 4-methyl-5-oxo-pentanoate and 1-methylheptyl-triphenylphosphonium iodide, and of (±)-syn-4,6-dimethyldodecanal starting from 3,5-dimethyl-2-cyclohexen-1-one. Direct GC–MS comparison of these synthetic samples with the natural pheromone allowed its unambiguous identification.
Sex pheromones and trail-following pheromone in the basal termites Zootermopsis nevadensis (Hagen) and Z. angusticollis (Hagen) (Isoptera: Termopsidae: Termopsinae)
In the context of an evolutionary study of the chemical communication in termites, sex pheromones and trail-following pheromones were investigated in two Termopsidae, Zootermopsis nevadensis and Z. angusticollis. In these species, in which the presence of sex-specific pheromones has been demonstrated previously, the chemical structure of the female sex pheromone has now been identified as (5E)-2,6,10-trimethylundeca-5,9-dienal and the male sex pheromone as (+)- or (-)-syn-4,6-dimethyldodecanal. The amount of sex pheromone was estimated at 5-10 ng per individual in females and 2-5 ng in males. Because these two sympatric species do not differ in their pheromonal chemical composition, reprodu…
ChemInform Abstract: New Macrolactones from the Defensive Salivary Secretion of Soldiers of the African Termite Pseudacanthotermes spiniger.
The salivary defensive secretion of large soldier termites of the species Pseudacanthotermes spiniger contains two novel macrocyclic lactones [22-keto-hexacosanolide (2) and 2-hydroxy-24-keto-octacosanolide (3)] together with the already known macrolactone hexacosanolide (1). In addition, the secretion contains important amounts of a polysaccharide based mainly upon β-glucopyranose, β-glucosamine and N-acetyl-β-glucosamine in equal amount.
New macrolactones from the defensive salivary secretion of soldiers of the african termite Pseudacanthotermes spiniger
The salivary defensive secretion of large soldier termites of the species Pseudacanthotermes spiniger contains two novel macrocyclic lactones [22-keto-hexacosanolide (2) and 2-hydroxy-24-keto-octacosanolide (3)] together with the already known macrolactone hexacosanolide (1). In addition, the secretion contains important amounts of a polysaccharide based mainly upon β-glucopyranose, β-glucosamine and N-acetyl-β-glucosamine in equal amount.