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Compound - E8E10-12OH


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Formula: C12H22O 
CAS#: 33956-49-9 
MW: 182.31 

[MS]  [ NMR ]  [ Kovats ]  [Behavioural function]  [Chemdraw

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Reference(s) for synthesis of (E,E)-8,10-Dodecadien-1-ol

Babler, J.H., and Haack, R.A. 1982. A facile stereoselective route to the sex pheromone of the codling moth via thermolysis of an allylic sulfoxide. J. Org. Chem. 47:4801-4803.
Bestmann, H.J., Suess, J. and Vostrowsky, O. 1978. Pheromone XX. Synthese von (E)-8,(E)-10-dodecadien-1-ol (codlemone), dem sexuallockstoff des apfelwicklers, seiner isomeren, homologen und derivate. Tetrahedron Lett. 19:3329-3332.
Bjoerkling, F., Norin, T., and Unelius, R. 1985. Synthesis of 8Z,10Z-dodecadienyl acetate using a general method applicable to Z,Z-1,3-dienes. Synth. Comm. 15:463-472.
Brovko, V.V., Mazur, V.G., Vlasov, A.A., Shishmakova, T.G., Strepkova, L.S., and Evstifeev, A.V. 1980. Synthesis of sex pheromones of codling and plum fruit moths and the housefly. Khim. Sel'sk. Khoz. 18:30.
Bulina, V.M., Kislitsyna, T.I., Ivanov, L.L., and Pyatnova, Yu.B. 1975. Synthesis of trans, trans-8,10-dodecadien-1-ol, a codling moth (Carpocapsa pomonella) pheromone. Khemo. Nasek. 2:211.
Butt, B.A., McGovern, T.P., Beroza, M., and Hathaway, D.O. 1974. Codling moth: cage and field evaluations of traps baited with a synthetic sex attractant. J. Econ. Entomol. 67:37.
Chisholm, M.D., Reed, D.W., Underhill, E.W., Palaniswamy, P., and Wong, J.W. 1985. Attraction of tortricid moths of subfamily Olethreutinae to field traps baited with dodecadienes. J. Chem. Ecol. 11:217-230.
Descoins, C., and Henrick, C.A. 1972. Stereoselective synthesis of a sex attractant of the codling moth. Tetrahedron Lett. 30:2999-3002.
George, D.A., McDonough, L.M., Hathaway, D.O., and Moffitt, H.R. 1975. Inhibitors of sexual attraction of male codling moths. Environ. Entomol. 4:606.
Hathaway, D.O., McGovern, T.P., Beroza, M., Moffitt, H.R., McDonough, L.M., and Butt, B.A. 1974. An inhibitor of sexual attraction of male codling moths to a synthetic sex pheromone and virgin females in traps. Environ. Entomol. 3:522.
Henrick, C. 1977. The synthesis of insect sex pheromones. Tetrahedron. 33:1845-1889.
Herve du Penhoat, C., and Julia, M. 1986. Synthesis with sulfones. XLIV. Stereoselective preparation of E,E 1,3-dienes by elimination of benzenesulfinic acid from E homoallylic sulfones. Tetrahedron. 42:4807-4816.
Huang, W., Xiao, W., and Wang, J. 1986. Wittig reaction. IV. Stereoselective synthesis of the insect sex pheromone of Laspeyresia, (E,E)-8,10-dodecadienol. Youji Huaxue. 376.
Kaslitsyna, T.I., Bulina, V.M., Ivanov, S.L., and Pyatnova, Y.B. 1976. Synthesis of E,E-8,10-dodecadienol, pheromone of the codling moth. Khim. Sredstva. Zashch. Rast. 7:78.
Knox, G.R., and Thom, I.G. 1981. Simple stereospecific syntheses of some insect pheromones using the –Fe(CO)3 protecting group. J. Chem. Soc. Chem. Comm. 8:373-374.
Kovalev, B.G., Ishchenko, R.I., Roska, G., Nedopekina, S.F., and Platon, Y.Y. 1978. Synthesis of trans-8, trans-10-dodecadienol and the acetate of trans-7, cis-9-dodecadienol. Khemoretsept. Nasek. 33.
Manyaliene, Z.P., and Skirkyavichene, Z.Yu. 1980. The synthesis of trans, trans-8,10-dodecadien-1-ol and the determination of its biological activity by the electroantennogram method. Khemoretsept. Nasek. 73-75.
Meng, X.Z., Li, W.W., and Han, Y. 1996. Synthesis and field trials of a sex attractant of Cydia trasias Meyrick (Lepidoptera: Tortricidae). Sci. Silvae Sin. 32:150-153.
Mori, K. 1974. Simple synthesis of sex pheromones of codling moth and red bollworm moth by the coupling of Grignard reagents with allylic halides. Tetrahedron. 30:3807-3810.
Muntyan, G.E., Vaskan, R.N., Shamsurin, A.A., and Katlabuga, L.E. 1974. Nonstereospecific synthesis of codling moth attractant. Izv. Akad. Nauk. Mold. SSR. Ser. Biol. Khim. Nauk. 67.
Naoshima, Y., Nakagawa, E., Wakabayashi, S., and Hayashi, S. 1980. A new synthesis of (E,E)-8,10-dodecadien-1-ol sex pheromone of codling moth. Agric. Biol. Chem. 44:1419.
Odinokov, V.N, Balesina, G.G., Ishmuratov, G.Yu., Salimgareeva, I.M., Bogatova, N.G., Zelenova, L.M., Muslukhov, R.R., and Tolstikov, G.A. 1984. The pheromones of insects and their analogues X. The stereospecific synthesis of (E,E)-8,10-dodecadienol - sex pheromone of Laspeyresia pomonella based on the cooligomer of butadiene with trimethyl vinylsilane. Khim. Prir. Soed. 4:514.
Petraitis, J. 1975. Synthesis of trans, trans-8,10-dodecadien-1-ol, the sex pheromone of the female codling moth (Carpocapsa pomonella L.). Khemoretsept. Nasek. 209.
Roelofs, W., Comeau, A., Hill, A., and Milicevic, G. 1971. Sex attractant of the codling moth: characterization with electroantennogram technique. Science. 174:297.
Samain, D., Descoins, C., and Commercon, A. 1978. A short, stereoselective synthesis of 8E,10E-dodecadien-1-ol; the sex pheromone of the codling moth. Laspeyresia pomonella L. Synthesis. 5:388-389.
Schlosser, M., Tuong, H.B., and Schaub, B. 1985. The betaine-ylid route to trans-alkenols. Tetrahedron Lett. 26:311-314.
Shakova, F.A., Zorin, V.V., Musavirov, R.R., Safarov, M.G., Muslukhov, R.R., Kharisov, R.Y., Ishmuratov, G.Y., and Rakhmankulov, D.L. 1996. Synthesis of dodeca-8E,10E-dien-1-ol - the sex pheromone of Laspeyresia pomonella via the acetolysis of 4-propenyl-1,3-dioxane. Chem. Nat. Comp. 32:582-584.
Shim, Y.S., Choi, J.W., Kim, W.J., Park, H.K., and Park, Y.S. 1986. Study on synthesis of methyl-7-iodoheptanoate. J. Pharm. Soc. Korea. 30:348.
Tolstikov, G.A., Dzhemilev, U.M., and Khusnutdinov, R.I. 1978. Insect sex pheromones and their analogs. I. Synthesis of the sex attractant of the codling moth. Khim. Prir. Soedin. (Tashk.). 1:125.
Vig, O.P., Vig, A.K., Gauba, A.L., and Gupta, K.C. 1975. A new synthesis of trans-8-trans-10-dodecadien-1-ol. J. Ind. Chem. Soc. 52:541.
Yamada, S., Ohsawa, H., Suzuki, T., and Takayama, H. 1986. Stereoselective synthesis of (E)-, (E,Z)-, and (E,E)-conjugated dienes via alkylation of 3-sulfolenes as the key step. J. Org. Chem. 51:4934-4940.
Zakharkin, L.I., and Babich, S.I. 1982. Synthesis of 8E,10E-dodecadien-1-ol from methyl esters of 2,5-heptadienoic acids. Zh. Org. Khim. 18:2261.

Citation: El-Sayed AM 2014. The Pherobase: Database of Insect Pheromones and Semiochemicals. <>.
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