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Three highly odorous metabolites from an actinomycete: 2-Isopropyl-3-methoxy-pyrazine, methylisoborneol, and geosmin

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The highly odorous metabolites isopropylmethoxypyrazine, methylisoborneol, and geosmin were identified from aStreptomyces sp. Their role in the odor pollution of water is discussed. 2-Isopropyl-3-methoxypyrazine has not been reported previously from actinomycetes.

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  • Bear, I.J., andThomas R.G. 1964. Nature of Argillaceous odour.Nature 201:993–995.

    Google Scholar 

  • Bramwell, A.F., Payne, I.M., Riezebos, G., Ward P., andWells, R.D. 1972. Nuclear chlorination of alkylpyrazines.J. Chem. Soc., Perkin Trans. 1:2004–2007.

    Google Scholar 

  • Buttery, R.G., andLing, L.C. 1973. Earthy aroma of potatoes.J. Agric. Food Chem. 21:745–746.

    Google Scholar 

  • Cherry, A.K. 1962. Use of potassium permanganate in water treatment.J. Am. Water Works Assoc. 54:417–424.

    Google Scholar 

  • Committee Report. 1970. Research on Tastes and Odors.J. Am. Water Works Assoc. 62:59–62.

    Google Scholar 

  • Dougherty, J.D., Campbell, R.D., andMorris, R.L. 1966. Actinomycete: Isolation and identification of agent responsible for musty odors.Science 152:1372–1373.

    Google Scholar 

  • Gauntlett, R.B., andPackham, R.F. 1973. The removal of organic compounds in the production of potable water.Chem Ind. (London) 812–817.

  • Gerber, N.N. 1968. Geosmin, from microorganisms, istrans-1-10-dimethyl-trans-9- decalol.Tetrahedron Lett. 2971–2974.

  • Gerber, N.N. 1969. A volatile metabolite of actinomycetes, 2-methylisoborneol.J. Antibiot. (Tokyo) 22:508–509.

    Google Scholar 

  • Gerber, N.N. 1973. Volatile lactones from streptomyces.Tetrahedron Lett. 771–774.

  • Gerber, N.N., andLechevalier, H.A. 1965. Geosmin, an earthy-smelling substance isolated from actinomycetes.Appl. Microbiol. 13:935–938.

    Google Scholar 

  • Henley, D.E., Glaze, W.H., andSilvey, J.K.G. 1969. Isolation and identification of an odor compound produced by a selected aquatic actinomycete.Environ. Sci. Technol. 3:268–271.

    Google Scholar 

  • Kikuchi, T., Mimura, T., Harimaya, K., Yano, H., Arimoto, M., Masada, Y., andInoue, T. 1973. Odorous metabolite of blue-green algae:Schizothrix muelleri Nägeli collected in the southern basin of Lake Biwa. Identification of geosmin.Chem. Pharm. Bull. 21:2342–2343.

    Google Scholar 

  • Liebich, H.M., andAl-Babbili, O. 1975. Gas chromatographic-mass spectrometric study of volatile metabolites in urine of patients with diabetes mellitus.J. Chromatogr. 112. 539–550.

    Google Scholar 

  • Medsker, L.L., Jenkins D., Thomas J.F., andKoch, C. 1969. Odorous compounds in natural waters. 2-Exo-hydroxy-2-methylbornane, the major odorous compound produced by several actinomycetes.Environ. Sci. Technol. 3:476–477.

    Google Scholar 

  • Meigh, D.F., Filmer, A.A.E., andSelf, R. 1973. Growth-inhibitory volatile aromatic compounds produced bySolanum tuberosum tubers.Phytochemistry 12:987–993.

    Google Scholar 

  • Miller, A., Scanlan, R.A., Lee, J.S., Libbey, L.M., andMorgan, M.E. 1973. Volatile compounds produced in sterile fish muscle(Sebastes melanops) byPseudomonas perolens.Appl. Microbiol. 25:257–261.

    Google Scholar 

  • Morgan, M.E., Libbey, L.M., andScanlan, R.A. 1972. Identity of the musty-potato aroma compound in milk cultures ofPseudomonas taetrolens.J. Dairy Sci. 55:666.

    Google Scholar 

  • Murray, K.E.,Shipton, J., andWhttfield, F.B. 1970. 2-Methoxypyrazines and the flavour of green peasPisum sativum).Chem. Ind. (London) 897–898.

  • Piet, G.J., Zoeteman, C.J., andKraayeveld, A.J.A. 1972. Earthy smelling substances in surface waters of the Netherlands.Water Treat. Exam. 21:281–286.

    Google Scholar 

  • Rosen, A.A., Mashni, C.I., andSafferman, R.S. 1970. Recent developments in the chemistry of odour in water: The cause of earthy musty odour.Water Treat. Exam. 19:106–119.

    Google Scholar 

  • Seifert, R.M., Buttery, R.G., Guadagni, D.G., Black, D.R., andHarris, J.G. 1970. Synthesis of some 2-methoxy-3-alkylpyrazines with strong bell pepper-like odors.J. Agric. Food Chem. 18:246–249.

    Google Scholar 

  • Silvey, J.K.G., Glaze, W.H., Hendricks, A., Henley, D., andMatlock, J. 1968. Gas Chromatographic studies on taste and odor in water.J. Am. Water Works Assoc. 60:440–450.

    Google Scholar 

  • Sipma, G.,Van Der Wal, B., andKettenes, D.K. 1972. The structure of mucidone, a metabolite of a streptomyces species.Tetrahedron Lett. 4159–4160.

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Gerber, N.N. Three highly odorous metabolites from an actinomycete: 2-Isopropyl-3-methoxy-pyrazine, methylisoborneol, and geosmin. J Chem Ecol 3, 475–482 (1977).

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