Stereochemical Studies of Acyclic Isoprenoid Compounds I--Gas Chromatographic Analysis of Stereoisomers of a Series of Standard Acyclic Isoprenoid Acids

Abstract

A method for the stereochemical determination of acyclic isoprenoid acids has been developed from GC analysis of the methyl and (-)-menthyl esters of a number of synthetic standards of known stereochemistry, ranging from 4,8-dimethylnonanoic acid [I]† to 5,9,13,17-tetramethylocadecanoic acid [IX]. The complete elution orders of all the diastereoisomeric (-)-menthyl esters of 4,8-dimethylnonanoic [I]; 2,6,10-trimethylundecanoic [II]; 3,7,11-trimethyldodecanoic [III] and 4,8,12-trimethyltridecanoic [IV] acids respectively, have been established for GC on open-tubular columns coated with butanediol-succinate polyester phase.