Methyl geranate

Chlorochroa sayi males produce a pheromone consisting primarily of methyl geranate, with trace amounts of methyl citronellate and methyl dihydrofarnesoate [107]. Methyl geranate is readily available in multigram quantities from fractional distillation of the commercially available mixture of methyl geranate and methyl nerate (J.G. Millar, unpublished data), or the two isomers can be separated chromatographically [107]. 

Although a small amount of acyclic terpene acids such as geranic acid and citronel-lic acid occurs in many essential oils, often as esters, they are rarely used in perfume and flavor compositions. Methyl geranate is an intermediate in a-damascone synthesis and is sometimes needed in the reconstitution of essential oils. 

Fungal metabolism of methyl geranate by Colletotrichum nicotianae affords methyl / -(+ 6,7-dihydroxygeranate in 85% yield via methyl 5-(—)-6,7-epoxygeranate. Pseudomonas aeruginosa converts a-terpineol into p-mentha-1,4(8)-diene and borneol. ... 

The diacid corresponding to 114 is callosobruchic acid (115), and forms part of the copulation release pheromone of the azuki bean weevil, Callosobruchus chinensis Both chiral isomers have been synthesized by Mori et al. from methyl geranate epoxide (123). After scission of the epoxide group, the iodide 124 was made conventionally, then the chiral group was introduced using the Evans (R)- or (5)-prolinol propionamide enolate anion (125) (made with lithium diethylamide in tetrahydrofuran on the amide). Removal of the proline group... 

Freeman, P. K. and Siggel, L., The kinetics of photochemical deconjugation reactions of methyl geranate. Tetrahedron, 44, 5065, 1988. 

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