Colletes cunicularius

Colletes cunicularius HE Attraction of males to virgin females (3S)-(+)-Linalool 8 [35]... 

In recent years, there is only one example of a pheromone in solitary Apocrita being chemically identified. Chiral GC and chiral GC-EAD provided identification of (3S)-(+)-linalool 8 >99.9% e.e. as a mandibular gland mate attractant in both males and females of Colletes cunicularius. Male contact with a scented source could be initiated with 5 ng per lure (3S)-(+)-linalool, which may act as both a sex attractant and a food attractant [35]. 

Enantiomerically pure (5)-(+)-linalool was the main constituent in the extracts of the solitary bee Colletes cunicularius L. (Hymenoptera Col-letidae). Field tests using pure enantiomers and the racemate of linalool showed that the highest activity for male bees was for (5)-(+)-linalool. ... 

Mant, J., Brandli, C., Vereecken, N. J., Schulz, C.M., Francke, W. and Schiestl, F. P. (2005). Cuticular hydrocarbons as sex pheromone of the bee Colletes cunicularius and the key to its mimicry by the sexually deceptive orchid Ophrys exaltata. 

Tacke et al45 synthesized the enantiomers of sila-linalool (61) as shown in Figure 11. The starting material 60 was converted into ( )-61, which was resolved by GC to give both (+)-61 and (—)-61. Both enantiomers were bioactive as tested by electroantennographic detection (EAD) on the males of the vernal solitary bee Colletes cunicularius. There was no major difference between the bioactivity of the sila-pheromone 61 and the natural linalool. The substitution of a carbon atom by silicon provides a good example of bioisosterism. 

Bergstrom, G. (1974). Natural odoriferous compounds. X. Macrocyclic lactones in the Dufour gland secretion of the solitary bees Colletes cunicularius and Halictus calceatus (Hymenoptera, Apidae). Chem. Scr. 5, 39-46. 

Cane, J. H. and TengO, J. O. (1981) Pheromonal cues direct mate-seeking behavior of male Colletes cunicularius (Hymenoptera Colletidae). J. Chem. Ecol., 1, 427-36. 

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