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Neutral compounds from male castoreum of North American beaver,Castor canadensis

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Abstract

North American beavers (Castor canadensis) mark their territories with castoreum, the strong-smelling paste in their castor sacs. In their own territories, beavers respond with scent marking to experimental scent marks that consist of strange castoreum (or selected components). In part, the unique odor of castoreum is due to large amounts of phenolic compounds and neutral compounds. Purified neutral compounds were analyzed by GC. GC-MS, and NMR; identities of the neutral compounds were confirmed by comparing the properties of authentic compounds with those of the isolated compounds. We identified 13 neutral compounds that had not been reported before for castoreum. Most of these are oxygen-containing monoterpenes. Of the nine neutral compounds reported by Lederer (1949), only three are confirmed in our analysis; the other six neutral compounds are either absent or are not volatile enough to be detected by our methods. Eight compounds—6-methyl-l-heptanol, 4,6-dimethyl-l-heptanol, isopinocamphone, pinocamphone, two linalool oxides, and their acetates—were synthesized for structure identification and bioassays.

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References

  • Augustine, R.L. 1965. Catalytic Hydrogenation, Techniques and Applications in Organic Synthesis, 57. Marcel Dekker, New York.

    Google Scholar 

  • Bates, R.B., andThalacker, V.P. 1988. Nuclear magnetic resonance spectral parameters in bicyclo-[3.1.1]-heptanes, α-pinene, myrtenol and verbenone.J. Org. Chem. 33:1730–1739.

    Google Scholar 

  • Bollinger, K.S. 1980. Scent marking behavior of beaver (Castor canadensis). M.S. thesis. University of Massachusetts, Amherst. 186 pp.

    Google Scholar 

  • Brownlee, R.G., andSilverstein, R.M. 1968. A micro-preparative gas chromatography and a modified carbon skeleton determinator.Anal. Chem. 40:2077–2080.

    Google Scholar 

  • Corey, E.J., andSuggs, J.W. 1975. Pyridinium chlorochromate. An efficient reagent for oxidation of primary and secondary alcohols to carbonyl compounds.Tetrahedron Lett. 31:2647–2650.

    Google Scholar 

  • Couchman, F.M., Pinder, A.R., andBroraham, N.H. 1964. Studies on the essential oil ofCyperus africulatus L.Tetrahedron 20:2037–2045.

    Google Scholar 

  • Darby, U., Lamb, N., andMoney, T. 1978. Synthesis and absolute configuration of nojigiku alcohol.Can. J. Chem. 57:742–749.

    Google Scholar 

  • Dev, S., Narula, A.P.S., andYadav, J.S. 1982. CRC Handbook of Terpenoids. I: p. 137.

  • Dreger, E. 1941,n-Hexyl alcohol.Org. Syn. Coll. 1:306–308.

    Google Scholar 

  • Duddeck, H., andDietrich, W. 1989. Structure Elucidation by Modern NMR. Steinkopff Verlag, Darmstadt. pp. 7–28.

    Google Scholar 

  • Erskin, R.L., andKnight, S.A. 1960. NMR study of the isomeric pinocamphones.Chem. Ind. 1160–1161.

  • Felin, D., Melera, A., Seibl, J., andKováts. 1963. 167. Zur Kenntnis ätherischer Öle 2. Mitteilung. Die Struktur der sogenannten «Linalooloxide».Helv. Chim. Acta 46:1513–1536.

    Google Scholar 

  • Grønneberg, T. Ø. 1978. Analysis of a wax ester fraction from the anal gland secretion of beaver (Castor fiber) by chemical ionization mass spectrometry.Chem. Scr. 13:56–58.

    Google Scholar 

  • Grønneberg, T. Ø., andLie, T. 1984. Lipids of the anal gland secretion of beaver (Castor fiber).Chem. Scr. 24:100–103.

    Google Scholar 

  • Guenther, E. 1949. Individual essential oils of the plant families.Essent. Oils 3:437–439.

    Google Scholar 

  • Heikman, H., Baectstrom, P., andTorssell, K. 1968. Perester oxidation and NBS bromination of α-pinene.Acta Chem. Scand. 22:2034–2035.

    Google Scholar 

  • Herout, V., Motl, O., andŠorm, F. 1954.Coll. Czech. Chem. Commun. 19:990.

    Google Scholar 

  • Hodgdon, H.E. 1978. Social dynamics and behavior within an unexploited beaver (Castor canadensis) population. Ph.D. thesis. University of Massachusetts, Amherst. 292 pp.

    Google Scholar 

  • Houlihan, P.M. 1989. Scent mounding by beaver (Castor canadensis): Functional and semiochemical aspects. M.S. thesis. State University of New York, College of Environmental Science and Forestry, Syracuse. 184 pp.

    Google Scholar 

  • Jashi, V.S., Damedaran, N.P., andDev, S. 1968. Organic reactions in a solid matrix—I alumina-induced oxrane rearrangements.Tetrahedron 24:5817–5830.

    Google Scholar 

  • Johnson, W.S., Werthemann, L., Bartlett, R., Brocksom, T.J., Li, T., Faulkener, J.J., andPeterson, M.R. 1970. A simple stereoselective version of the Claisen rearrangement leading totrans-trisubstituted olefinic bonds. Synthesis of squalene.J. Am. Chem. Soc. 92:741–743.

    Google Scholar 

  • Julia, M., Descoins, C., andRise, C. 1966. Preparation and stereochemistry study of polyunsaturated alcohols obtained by homoallylic transfer.Tetrahedron Suppl. 2:443–462.

    Google Scholar 

  • Julia, S., Julia, M., Tchen, S., andGraffin, P. 1961. Some cases of vinylogous homoallylic rearrangement.Compt. Rend. 253(4):678–680.

    Google Scholar 

  • Kerschbaum, M. 1900. Ueber die aldehydischen Bestandtheile des Verbenaöles und über Verbenon.Chem. Ber. 33:885–893.

    Google Scholar 

  • Klein, E., Farnoe, H., andRojahn, W. 1964. Chemistry of linalool oxides.Ann. Chem. 675:73–82.

    Google Scholar 

  • Lederer, E. 1946. Chemistry and biochemistry of the scent glands of the beaver (Castor fiber).Nature 157:231–232.

    Google Scholar 

  • Lederer, E. 1949. Castoreum and ambergris: Chemical and biochemical constituents.Perfum. Essent. Oil Rec. 40:353–359.

    Google Scholar 

  • Levene, P.A., andAllen, C.H. 1916. The oxidation of branched chain fatty acids.J. Biol. Chem. 27:433–462.

    Google Scholar 

  • Marvel, C.S., andSekera, V.C. 1955.n-Dodecyl (lauryl)p-tolunesulfonate.Org. Syn. Coll. 3:366–367.

    Google Scholar 

  • Maurer, B., andOhloff, G. 1976. Zur Kenntnis der stickstoffhaltigen Inhaltsstoffe von Castoreum.Helv. Chim. Acta 59:1169–1185.

    Google Scholar 

  • Moffett, R.B. 1963. 2-(l-Pyrrolidyl)propanol.Org. Syn. Coll. 4:834–836.

    Google Scholar 

  • Müller-Schwarze, D. 1992. Castoreum of beaver (Castor canadensis): Function, chemistry and biological activity of its components. pp. 457–464.in R.L. Doty and D. Müller-Schwarze (eds.). Chemical Signals in Vertebrates 6. Plenum, New York.

    Google Scholar 

  • Müller-Schwarze D., andHeckman, S. 1980. The social role of scent marking in beaver (Castor canadensis).J. Chem. Ecol. 6:81–95.

    Google Scholar 

  • Müller-Schwarze D., andHoulihan, P.W. 1990. Pheromonal activity of single castoreum constituents in behaver,Castor canadensis.J. Chem. Ecol. 17:715–734.

    Google Scholar 

  • Müller-Schwarze, D., Morehouse, L., Corradi, R., Zhao, C.-H., andSilverstein, R.M. 1986. Odor images: Responses of beaver to castoreum fractions, pp. 561–570,in D. Duvall, D. Müller-Schwarze, and R.M. Silverstein (eds.). Chemical Signals in Vertebrates 4. Plenum, New York.

    Google Scholar 

  • Naves, Y.-R., Alves, H.M., Arndt, V.H., Gottlieb, O.R., andMagalhaes, M.T. 1963. 114. Etudes sur les matières végétales. CLXXXV. Sur les huiles essentielles de deux especes appartenant au genreCryptocaria.Helv. Chim. Acta 46:1056–1059.

    Google Scholar 

  • Nigam, I.C., andLevi, L. 1968. Essential oils and their constituents. XLII: Isomerization of epoxides on active alumina.Can. J. Chem. 46:1944–1947.

    Google Scholar 

  • Sadtler. 1980. Standard Spectra, NMR spectrum 52:30795M.

  • Sadtler. 1981. Standard Carbon-13 NMR Spectra, 57:11298C.

  • Scheline, R.R. 1991. Handbook of Mammalian Metabolism of Plant Compounds. CRC Press. Boca Raton, Florida, 514 pp.

    Google Scholar 

  • Schmidt, H. 1944. Zur Raumisomerie in der Pinanreihe (IV. Mitteil.*): Pinocarvon und die beiden diastereomeren Pinocarveole.Chem. Ber. 77:167–174.

    Google Scholar 

  • Schulte, B.A., Müller-Schwarze, D., Webster, F.X., andTang, R. 1994. Beaver (Castor canadensis) response to major phenolic and neutral compounds in castoreum.J. Chem. Ecol. 21:3063–3081.

    Google Scholar 

  • Schwartz, M.A., Crowell, J.D., andMusser, J.H. 1972. Biogenetically patterned approaches to eudesmane sesquiterpenes.J. Am. Chem. Soc. 94:4361–4363.

    PubMed  Google Scholar 

  • Shaligram, A.S.R., andBhattacharyya, S.C. 1962. Terpenoids—XXXII. Absolute configuration of junenol and laevojunenol and synthesis of junenol from costunolide.Tetrahedron 18:969–977.

    Google Scholar 

  • Shimizu, S., Karasawa, D., andIkeda, N. 1966. A new mint (variety ofMentha aquatica L.) containing (—)-isopinocamphone as a major constituent of essential oil.Agric. Biol. Chem. 30:200–201.

    Google Scholar 

  • Stevens, P.G. 1943. American musk. II. A preliminary note on the scent glands of the beaver.J. Am. Chem. Soc. 65:2471.

    Google Scholar 

  • Svendsen, G.E. 1980. Patterns of scent-mounding in a population of beaver (Castor canadensis).J. Chem. Ecol. 6:133–148.

    Google Scholar 

  • Svendsen, G.E., andHuntsman, W.D. 1988. A field bioassay of beaver castoreum and some of its components.Am. Midl. Nat. 120:144–149.

    Google Scholar 

  • Tang, R., Webster, F.X., andMüller-Schwarze, D. 1993. Phenolic compounds from male castoreum of the North American beaver,Castor canadensis.J. Chem. Ecol. 19:1491–1500.

    Google Scholar 

  • Uchio, Y. 1977. Constituents of the essential oil ofChrysanthemum japonnense. Nojigiku alcohol and its acetate.Bull. Chem. Soc. Jpn. 51(8):2342–2346.

    Google Scholar 

  • Valenta, Z., Khaleque, A., andRashid, M.H. 1960.cis-Cyclohexane-1,2-diol in the beaver gland.Experientia 17:130.

    Google Scholar 

  • Walbaum, H., andRosenthal, A. 1927. Odoriferous substances in castoreum.J. Prakt. Chem. 117:225–232.

    Google Scholar 

  • Welsh, R.G., andMüller-Schwarze, D. 1989. Experimental habitat scenting inhibits colonization by beaver,Castor canadensis.J. Chem. Ecol. 15:887–893.

    Google Scholar 

  • Wilt, J.W., Massie, S.N., andDabet, R.B. 1970. Reaction of 2-(3-cyclopentenyl)-ethyl bromide with tri-n-butyltin hydride. Cyclization to norbonane.J. Org. Chem. 35:2803–2806.

    Google Scholar 

  • Zweifel G., andBrown, H.C. 1964. Hydrogenation of terpenes.J. Am. Chem. Soc. 86:393–397.

    Google Scholar 

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Authors and Affiliations

  1. Department of Chemistry, State University of New York College of Environmental Science and Forestry, 13210, Syracuse, New York

    Rong Tang & Francis X. Webster

  2. Department of Biology, State University of New York College of Environmental Science and Forestry, 13210, Syracuse, New York

    Dietland Müller-Schwarze

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  1. Rong Tang
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  2. Francis X. Webster
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Tang, R., Webster, F.X. & Müller-Schwarze, D. Neutral compounds from male castoreum of North American beaver,Castor canadensis . J Chem Ecol 21, 1745–1762 (1995). https://doi.org/10.1007/BF02033674

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