5(Z)-Dodecenoic acid is a medium-chain unsaturated fatty acid. It is a precursor in the biosynthesis of the sex pheromone 5(Z)-dodecenal.1 5(Z)-Dodecenoic acid levels are increased in culture medium from MCF-7 breast cancer cells compared to KMST-6 fibroblasts.2 Levels of 5(Z)-dodecenoic acid are increased in the plasma of patients with medium-chain acyl-CoA dehydrogenase (MCAD) deficiency, an inborn error of metabolism characterized by hypoketotic hypoglycemia, medium-chain dicarboxylic aciduria, and intolerance to fasting.3
1.Bestmann, H.J., Attygalle, A.B., Garbe, W., et al.Chemical structure and final steps of biosynthesis of the female sex pheromone of Gastropacha quercifolia (Lepidoptera: Lasiocampidae)Insect Biochem. Molec. Biol.23(7)793-799(1993) 2.Tanaka, M., Hsuan, C., Oeki, M., et al.Identification of characteristic compounds of moderate volatility in breast cancer cell linesPLoS One15(6)e0235442(2020) 3.Onkenhout, W., Venizelos, V., van der Poel, P.F.H., et al.Identification and quantification of intermediates of unsaturated fatty acid metabolism in plasma of patients with fatty acid oxidation disordersClin. Chem.41(10)1467-1474(1995)