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Compound - megatomoic acid

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(E,Z)-3,5-Tetradecadienoic acid Formula:  C14H24O2  CAS#:  17022-64-9  MW:  224.34  [MS]  [ NMR ]  [Behavioural function]  [Chemdraw]

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Reference(s) for synthesis of (E,Z)-3,5-Tetradecadienoic acid Abrams, S.R. 1982. Isomerization of acetylenic acids with sodium salt of 1,2-diaminoethane: a one step synthesis of megatomoic acid. Can. J. Chem. 60:1238-1243.   Abrams, S.R., Quail, J.W., and Delbaere, L.T.J. 1983. Base mediated dimerization of 2-tetradecynoic acid. Can. J Chem. 615:2449.   DeJarlais, W.J., and Emken, E.A. 1986. New synthesis of cis-3, cis-5- and trans-3, cis-5-tetradecadienoic acids, pheromone constituents of Attagenus elongatulus and A. megatoma. Lipids. 21:662.   DeJarlais, W.J., and Emken, E.A. 1987. Stereospecific synthesis of (Z,Z)-3,5-tetradecadienoic acid, a component of Attagenus elongatulus (Casey) pheromone. J. Chem. Ecol. 13:179-184.   Ikeda, Y., Ukai, J., Ikeda, N., and Yamamoto, H. 1987. Selective proton transfer of unsaturated esters. Syntheses of a trail-following pheromone for subterranean termites and megatomoic acid. Tetrahedron. 43:743-753.   Ragoussis, V., Panopoulou, M., and Ragoussis, N. 2004. Concise preparation of the (3E,5Z)-alkadienyl system. New approach to the synthesis of principal insect sex pheromone constituents. J. Agric. Food Chem. 52:5047-5051.   Rodin, J.O., Leaffer, M.A., and Silverstein, R.M. 1970. Synthesis of trans-3,cis-5-tetradecadienoic acid (megatomoic acid), the sex attractant of the black carpet beetle, and its geometric isomers. J. Org. Chem. 35:3152-3154.   Silverstein, R.M., Rodin, J.O., Burkholder, W.E., and Gorman, J.E. 1967. Sex attractant of the black carpet beetle. Science. 157:85.   Tsuboi, S., Masuda, T., and Takeda, A. 1983. A stereoselective synthesis of (3E,5Z)-3,5-tetradecadienoic acid (megatomoic acid), the sex attractant of the black carpet beetle. Bull. Chem. Soc. Jpn. 56:3521-3522.   Yokoi, K., and Matsubara, Y. 1979. Studies on the synthesis of sex pheromone of the black carpet beetle. Kinki Daigaku Riko. Kenkyu Hokoku. 65.