Farnesoic acid

Synthesis of [12-3H]-farnesoic acid and [13-3H]-farnesyl diazomethyl ketone... 

This Asian species is a major agricultural pest. The pheromone has been proposed to consist of three male-specific compounds, only one of which, (Z)-exo-a-bergamotenal 150, has been reported in the literature [114]. The racemic compound was synthesized starting from farnesoic acid chloride 146 (Scheme 25) [114]. Thus, the vinyl ketene prepared from acid chloride 146 underwent 2+2 cycloaddition to give bicyclic ketone 147. The ketone function was removed by reaction with hydrazine followed by treatment of the resulting hy-... 

The three major, known insect juvenile hormones (JH I, JH II and JH III) (Figure 6) are all methyl esters of terminally epoxi-dized homologs of farnesoic acid. They are present in varying amounts in different insects at different stages of development and it has been suggested, though not determined, that they may play different hormonal roles. 

The farnesoic acid precursors of the juvenile hormones are synthesized by appropriate isoprenoid routes from acetyl CoA and/or propionyl CoA and subsequently undergo 10,11-epoxidation and methylation of the carboxylic acid group by -methyl transferase (36) (Figure 7). It is not yet fully ascertained whether in vivo farnesoic acid is epoxidized prior to methylation or whetfilr the order of these two terminal reactions is reversed. 

Figure 2. Cumulative JH sjmthesis in vitro by CA of immature (2-3 days) adult female locusts. The first 5 hr demonstrate basal synthesis. I = addition of either 50ul farnesoic acid (FA) ( ) or allatotropin (0) for an additional 4 hr incubation. II - transfer of the allato tropin-treated CA to FA-supplemented media, and FA-treated CA to allato tropin-supplemented media. Values are the mean SE of 11 replicates. The error bars of the 1 hr incubation have been placed above and beside the values in order not to obscure them.

Law et al. (1966) obtained by the addition of hydrochloric acid to farnesoic acid... 

PopjAK, G., R. H. CoRNFORTH, and K. Clifford Inhibition of cholesterol biosynthesis by farnesoic acid and its analogues. Lancet 1960/1, 1270. 

Ding, Q. and Tobe, S.S. (1991) Production of farnesoic acid and methyl farnesoate by mandibular organs of the crayfish, Procambarus clarkii. Insect Biochem., 21, 285-291. 

C7 Diploptera punctata Farnesol, farnesal, famesoic acid, methyl farneso- [251] ... 

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