Octadecane, 9,10-epoxy

Its longest continuous chain contains 18 carbon atoms, and so it is named as an epoxy derivative of octadecane. Number the chain in the direction that gives the lowest number to the carbons that bear oxygen. Thus, disparlure is d.v-2-mcthyl-7,8-cpoxyoctadccanc. 

The cis-isomer that is shown is the natural sex pheromone of the gypsy moth. Disparlure is an aliphatic hydrocarbon (methyl-octadecan) with an epoxy group. It is used as an attractant and is formulated in plastic flakes. The racemic mixture may also be used. 

The first materials produced by this method which have obtained commercial importance are monoepoxides such as octylene oxide, dodecene oxide, and a mixture of 1,2-epoxy hexadecane and 1,2-epoxy octadecane. These epoxides are used as stabilizers for vinyl polymers and as diluents for epoxy resins. 

Bombyx mori. L. dispar has an epoxide moiety present in the most active identified pheromone blend component (JR, 85) 7,8-epoxy-2-methyl-octadecane ((+)... 

Alkanes and alkenes containing about 30 C-atoms are constituents of plant cuti-cular waxes and the surface lipids of microorganisms and animals (D 3.2.4). These waxes play an important role in the hardiness and in the water economy of plants (E 2.2, E 5.4). Undecane, CH3(CH2)9CH3 tridecane, CH3(CH2)nCH3 and pentadecane, CH3(CH2)i3CH3 are alarm pheromones of ants. 7,8-Epoxy-2-methyl-octadecane is a sex pheromone of Lymantria dispar. In brown algae... 

Epoxy-2-methyl-octadecane (D 3.2.2) Sex pheromone of 5 Lymantria dispar... 

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