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¦ « Previous CompoundE2-9OH    Next Compound »E2-9R-hydroxy-decenoic acid ¦
Compound - E2-9-oxo-10Acid [(E)-9-oxo-2-Decenoic acid]

Bedoukain RussellIPM
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(E)-9-oxo-2-Decenoic acid
(E)-9-oxo-2-Decenoic acid

Formula: C10H16O3 
CAS#: 334-20-3 
MW: 184.23 

[MS]  [ NMR ]  [Behavioural function

Dots surface:

Reference(s) for synthesis of (E)-9-oxo-2-Decenoic acid [E2-9-oxo-10Acid]

Barbier, M., and Huegel, M.-F. 1961. Syntheses dans la serie de l'acide ceto-9 decene-2 trans-oique (substance Royale). Bull. Soc. Chem. Fr. 28:951-954.
Barbier, M., and Lederer, E. 1960. Structure chimique de la substance royale de la riene d' abeille (Apis mellifica). C.R. Acad. Sci. (Paris). 250:4467.
Barbier, M., Lederer, E., and Nomura, T. 1960. Synthese de l'acide ceto-9-decene-2 trans-oique (substance Royale) et de l'acide ceto-8-nonene-2 trans-oique. C.R. Acad. Sci. (Paris). 251:1133.
Bestmann, H.J., Kunstmann, R., and Schulz, H. 1966. Reaktionen mit phosphinalkylenen XV. Eine synthese der "koeniginnensubstanz" und der trans- 10-hydroxy-decen-(Z)-saeure-(l) (Royal jelly acid ). Liebigs Ann. Chem. 699:33.
Butler, C.G., Callow, R.K., and Johnston, N.C. 1961. The isolation and synthesis of queen substance 9-oxodec-trans-2-enoic acid, a honeybee pheromone. Proc. Roy. Soc. B155:417.
Callow, R.K., and Johnston, N.C. 1960.The chemical constitution and synthesis of queen substance of honeybees (Apis mellifera). Bee World. 41:152.
Chattopadhyay, A., Mamdapur, V.R., and Chadha, M.S. 1983. Synthesis of queen bee and cabbage looper pheromones from aleuritic acid. Ind. J. Chem. 22B:158-159.
Doolittle, R.E., Blum, M.S., and Boch, R. 1970. cis-9-oxo-2-decenoic acid synthesis and evaluation as a honey bee pheromone and masking agent. Ann. Entomol. Soc. Am. 63:1180.
Dzhemilev, U.M., Balezina, G.G., and Tolstikov, G.A. 1980. Insect pheromones and their analogs. IV. The synthesis of the sex attractant of the honey bee Apis mellifera. Khim. Prir. Soedin. 3:387-389.
Eiter, K. 1961. Neue synthesen der koeniginnensubstanz. Angew. Chem. 73:619.
Eiter, K. 1962. Neue synthesen der 'koeniginnsubstanz' und der 9-hydroxy-2-trans-decensaeure. Liebigs Ann. Chem. 91-99.
Ferroud, D., Gaudin, J.M., and Genet, J.P. 1986. Bis(arylsulfonyl)methane: a versatile synthon in pheromone synthesis. Tetrahedron Lett. 27:845-846.
Hase, T.A., and McCoy, K. 1979. Synthesis of the next lower homologues of carboxylic acids. A convenient route to the queen substance and to 9-oxodecanoic acid, a prostaglandin intermediate. Synth. Comm. 9:63.
Huggenberg, W., and Hesse, M. 1983. 143. Synthesen von omega-substituierten omega-nitrocarbonsaeureestern aus alpha-nitrocycloalkanonen. Helv. Chim. Acta. 66:1519-1524.
Ishmuratov, G.Y., Yakovleva, M.P., Botsman, L.P., Ishmuratova, N.M., Muslukhov, R.R., Khambalova, G.V., and Tolstikov, G.A. 2003. Synthesis of a multifunctional pheromone of the honeybee Apis mellifera via condensation of 7-oxooctanal with malonic acid. Chem. Nat. Comp. 39:28-30.
Jaeger, R.H., and Robinson, R. 1961. A simple synthesis of "queen substance". Tetrahedron. 14:320-321.
Kennedy, J., McCorkindale, N.J., and Raphael, R.A. 1961. A new synthesis of queen substance. J. Chem. Soc. 3813-3815.
Kovalev, G.G., Vasokan, R.N., and Laveinenko, E.S. 1971. Substituted acetals in organic synthesis. A new synthesis of trans-9-oxodec-2-enoic acid ("queen substance") and trans-9-hydroxydec-2-enoic acid. Zhur. Org. Khim. 7:667-670.
Kyskina, A.S., Gankina, L.V., Ivanov, L.L., Pyatnova, Yu.B., and Evstigneeva, R.P. 1971. Synthesis of trans-9-keto-2-decenoic and trans-9-hydroxy-2-decenoic acids. Zhur. Org. Khim. 7:51-55.
Majee, R.N., Ramani, R., and Mukherjee, S.N. 1983. Synthesis of queen bee pheromone. Current Sci. 52:320-321.
Naoshima, Y., Ike, H., Ogawa, T., Nakayama, T., and Kondo, H. 1984. An easy synthesis of (E)-9-oxo-2-decenoic acid, the queen substance of the honey bee, and (Z)-6-heneicosen-11-one, the sex pheromone of the Douglas fir tussock moth. Agric Biol. Chem. 48:2151.
Odinokov, V.N., Ishmuratov, G.Y., Ladzikova, I.M., and Tolstikov, G.A. 1986. Pheromones of insects and their analogs. XV. Synthesis of 9-oxo-2E-decenoic acid - pheromone of honey-bee, Apis mellifera. Khim. Prir. Soedin. 5:632-634.
Ogura, K., Sanada, K., Takahashi, K., and Iida, H. 1982. A novel method for preparation of 2-(methyl- or phenylthio)alkanoic esters. Tetrahedron Lett. 23:4035-4038.
Petraitis, J.K., and Dauksas, V.K. 1980. Synthesis of the honeybee queen's pheromones and their structural analogues Apis mellifica (L.). Khemoretsept. Nasek. 55-67.
Shearer, D.A., Boch, R., Morse, R.A., and Laigo, F.M. 1970. Occurrence of 4-oxodec-trans-2-enoic acid in queens of Apis dorsata, Apis cerana, and Apis mellifera. J. Insect Physiol. 16:1437.
Sisido, K., Kawanisi, M., Kondô, K., Morimoto, T., Saitô, A., and Hukue, N. 1962. Syntheses of 9-keto- and 10-hydroxy-trans-2-decenoic acids and related compounds. J. Org. Chem. 27:4073-4076.
Subramaniam, C.S., Thomas, P.J., Mamdapur, V.R., and Chadha, M.S. 1978. A convenient synthesis of queen bee pheromone. Ind. J. Chem. 16B:318-319.
Taksidi, V.Kh, Laurenko, S.G., Shkolina, L.A., Shaposhnikova, N.G., and Pyatnova, Yu.B. 1979. Synthesis and new aspects of the biological action of E-9-keto-2-decenoic acid one of the components of bee pheromones. Nov. Khim. Sredstva. Zashchityrast. 37.
Tamaru, Y., Yamada, Y., and Ysohida, Z.-I. 1978. palladium catalyzed thienylation of alpha-methallyl alcohol with 5-substituted 2-bromothiophenes and its application to synthesis of queen substance. Tetrahedron Lett. 19:919-922.
Trost, B.M., and Hiroi, K. 1976. New synthetic reactions. Oxidative seco rearrangement. J. Am. Chem. Soc. 98:4313-4315.
Trost, B.M., and Salzmann, T.N. 1975. Applications of sulfenylations of ester enolates. Synthesis of pheromones of the honey bee. J. Org. Chem. 40:148-150.
Trost, B.M., Hiroi, K., and Jungheim, L.N. 1980. Oxidative seco rearrangement. A novel carbon-carbon bond cleavage. J. Org. Chem. 45:1839-1847.
Trost, B.M., Salzmann, T.N., and Hiroi, K. 1976. New synthetic reactions. Sulfenylations and dehydrosulfenylations of esters and ketones. J. Am. Chem. Soc. 98:4887-4902.
Tsuji, J., Masaoka, K., and Takahashi, T. 1977. Simple synthesis of queen substance from the butadiene telomer. Tetrahedron Lett. 18:2267-2268.
Vig, O.P., Vig, A.K., and Grewal, M.S. 1975. A new synthesis of 9-keto-trans-2-decenoic acid. J. Ind. Chem. Soc. 52:543.
Villemin, D. 1986. Olefin oxidation: a synthesis of queen bee pheromone. Chem. Ind. (London). 69.
Yokoi, K., and Matsubara, Y. 1978. Studies on the syntheses of Royal jelly acid, queen substance and their related compounds. Fac. Sci. Tech. Kinki Univ. Nippon Kagaku Kaishi. 1415.
Yokoi, K., and Matsubara, Y. 1979. Studies on the synthesis of physiologically active compounds. I. Studies on the synthesis of Royal jelly acid, queen substance and related compounds. J. Chem. Soc. Jpn. 10:1415.

Citation: El-Sayed AM 2024. The Pherobase: Database of Pheromones and Semiochemicals. <>.
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