Comparison of three derivatives for the enantiomeric separation of chiral alcohols and the absolute configuration of Myrmica ant 3-octanol

Athula B. Attygalle, E. David Morgan, Richard P. Evershed, Steven J. Rowland

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Abstract

A comparison of ease of preparation, retention times gas chromatographic separation factors of three derivatives for the microscale determination of enantiomeric composition of chiral alcohols is described using 3-octanol as the model compound. Of the three derivatives, N-trifluoroacetyl-(S)-(+)-alanyl ester, N-trifluoroacetyl-(S)-(-)-prolyl ester and (+)-trans-chrysanthemoyl ester, the last was found to be the most useful and was employed to establish the elution order of the (+)-trans-chrysanthemate esters of 3-octanol. Thereby 3-octanol, a pheromone component from the mandibular glands of three species of Myrmica ants was shown to consist essentially of the R enantiomer with a small amount of S enantiomer.

Original languageEnglish
Pages (from-to)411-417
Number of pages7
JournalJournal of Chromatography A
Volume260
Issue numberC
DOIs
StatePublished - 1983

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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