Stability of epoxide-containing juvenoids to dilute aqueous acid

Susanne M. Mumby, Bruce D. Hammock

Research output: Contribution to journalArticle

15 Scopus citations

Abstract

The morphogenetic activity on Tenebrio molitor and the stability in weak aqueous acid of 13 p-bromophenyl geranyl ether epoxides containing juvenile hormone mimics, radiolabeled juvenile hormone, and three additional nonhalogenated hormone mimics were examined. Although changes in the molecule remote to the epoxide caused variations in hydrolytic stability, major changes resulted from varying the substituents on the epoxide. Increasing the size of alkyl substituants on the epoxide resulted in increased hydrolytic stability, and mono- and disubstituted epoxides were more stable than tri- and tetrasubstituted epoxides. As a derivatization technique, conversion of a trisubstituted epoxide to its diol proved unreliable when sulfuric acid in aqueous tetrahydrofuran was used but quantitative when dilute aqueous buffers were used.

Original languageEnglish (US)
Pages (from-to)1223-1228
Number of pages6
JournalJournal of Agricultural and Food Chemistry
Volume27
Issue number6
StatePublished - 1979

ASJC Scopus subject areas

  • Agricultural and Biological Sciences (miscellaneous)
  • Food Science
  • Chemistry (miscellaneous)

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