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

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.