Journal of Chemical Ecology

, Volume 3, Issue 3, pp 309–319 | Cite as

Syn- andanti-phenylacetaldehyde oxime two novel testosterone-dependent mammalian metabolites

  • Amos B. SmithIII
  • Kevin J. Byrne
  • Gary K. Beauchamp


Domestic guinea pigs having high levels of circulating testosterone (i.e., males and castrate males receiving testosterone propionate injections) excrete in their urine equal amounts of both thesyn andanti isomers of phenylacetaldehyde oxime, while those guinea pigs having low testosterone titers (i.e., females, castrate males, and juveniles) excrete neither. These aldoximes were also detected in the urine of wild male guinea pigs. Radiolabeling studies in the domestic guinea pigs strongly suggest that these aldoximes are derived from phenylalanine. To our knowledge this is the first observation and isolation of phenylacetaldehyde oxime from a mammalian source. The significance of these components in phenylalanine metabolism as well as in guinea pig chemical communication is discussed.

Key words

chemical communication phenylalanine metabolism guinea pig urinary metabolites phenylacetaldehyde oxime 


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Copyright information

© Plenum Publishing Corp. 1977

Authors and Affiliations

  • Amos B. SmithIII
    • 1
  • Kevin J. Byrne
    • 1
  • Gary K. Beauchamp
    • 1
  1. 1.The Monell Chemical Senses Center and The Department of ChemistryUniversity of PennsylvaniaPhiladelphia

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