Abstract
Urine of the black-tailed deer is the source of the “deer lactone,” which is deposited on the tarsal gland tufts by “rub-urination.” The enantiomer composition of the lactone from the urine of the female is 89(R)-(−)/11(S)-(+). Responses by deer were strongest toward the synthetic racemic lactone in the social test and toward the natural lactone in the choice test. In both tests, the (−)- lactone released slightly stronger responses than its enantiomer.
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Borden, J.G., Chong, L., McLean, J.A., Slessor, K.N., andMori, K. 1976.Gnathotrichus sulcatus: Synergistic response to enantiomer of the aggregation pheromone sulcatol.Science 192:894–896.
Brownlee, R.G., andSilverstein, R.M. 1968. A micro-preparative gas chromatograph and a modified carbon skeleton determinator.Analyt. Chem 40:2077–2079.
Brownlee, R.G., Silverstein, R.M., Müller-Schwarze, D., andSinger, A.G. 1969. Isolation, identification and function of the chief component of the male tarsal scent in black-tailed deer.Nature 221:284–285.
Friedman, L., andMiller, J.G. 1971. Odor incongruity and chirality.Science 172:1044–1046.
Iwakj, I., Marumo, S., Saito, T., Yamada, M., andKatagiri, K. 1974. Synthesis and activity of optically active disparlure.J. Am. Chem. Soc. 96:7842–7844.
Kafka, W.A., Ohloff, G., Schneider, D., andVareschi, E. 1973. Olfactory discrimination of two enantiomers of 4-methylhexanoic acid by the migratory locust and the honey-bee.J. Comp. Physiol. 87:277–284.
Lanier, G.N., College of Environmental Science and Forestry, personal communication.
Leitereg, T.J., Guadagni, D.G., Harris, J., Mon, T.R., andTeranishi, R. 1971. Evidence for the difference between the odours of the optical isomers (+)- and (−)-carvone.Nature 230:455–456.
Lensky, Y., andBlum, M.S. 1974. Chirality in insect receptors.Life Sci. 14:2045–2049.
Levinson, H.Z., Max Planck Institute, Seewiesen, West Germany, personal communication.
Müller-Schwarze, D. 1971. Pheromones in black-tailed deer.Anim. Behav. 19:141–152.
Müller-Schwarze, D., Silverstein, R.M., Müller-Schwarze, C., Singer, A.G., andVolkman, N.J. 1976. Response to a mammalian pheromone and its geometric isomer.J. Chem. Ecol. 2:389–398.
Müller-Schwarze, D., Volkman, N.J., andZemanek, K.F. 1977. Osmetrichia: Specialized scent hair in black-tailed deer.J. Ultrastruct. Res. 59:223–230.
Pirkle, W.H., Sikkenga, D.L., andPavlin, M.S. 1977. Nuclear magnetic resonance determination of enantiomeric composition and absolute configuration of γ-lactones using chiral 2,2,2,-trifluoro-1-(9-anthryl)-ethanol.J. Org. Chem. 42:384–387.
Ravid, U., andSilverstein, R.M. 1977. General synthesis of optically active 4-alkyl (or alkenyl)-γ-lactones from glutamic acid enantiomers.Tetrahedron Lett. 5:423–426.
Ravid, U., andSilverstein, R.M. 1978. Synthesis of the enantiomers of 4-substituted-γ-lactones with known absolute configuration, and demonstration of the optical purity.Tetrahedron. In press.
Riley, R.G., Silverstein, R.M., andMoser, J.C., 1974a. Biological responses ofAtta texana to its alarm pheromone and the enantiomer of the pheromone.Science 183:760–762.
Riley, R.G., Silverstein, R.M., andMoser, J.C. 1974b. Isolation, identification, synthesis, and biological activity of volatile compounds from the heads ofAtta ants.J. Insect Physiol. 20:1629–1637.
Russell, G.F., andHills, J.I. 1971. Odor differences between enantiomeric isomers.Science 172:1043–1044.
Staedler, E. 1974. Host plant stimuli affecting oviposition behavior of the eastern spruce budworm.Entomol. Exp. Appl. 17 (Biol Abstr. 58, Abstr No. 60201, 1974).
Tumlinson, J.H., Klein, M.S., Doolittle, R.E., Ladd, T.C., andProveaux, A.T. 1977. Identification of the female Japanese beetle sex pheromone: Inhibition of male response by an enantiomer.Science 187:789–792.
Vité, J.P., Hedden, R., andMori, K. 1976.Ips grandicollis: Field response to the optically pure pheromone.Naturwissenschaften 63:43.
Wood, D.L., Browne, L.E., Ewing, B., Lindahl, K., Bedard, W.D., Tilden, P.E., Mori, K., Pitman, G.B., andHughes, P.R. 1976. Western pine beetle: Specificity among enantiomers of male and female components of an attractant pheromone.Science 192:896–898.
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Odocoileus hemionus columbianus.
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Müller-Schwarze, D., Ravid, U., Claesson, A. et al. The “deer lactone”. J Chem Ecol 4, 247–256 (1978). https://doi.org/10.1007/BF00988059
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DOI: https://doi.org/10.1007/BF00988059