Chirality Evaluation of 2-Heptanol and Z-4-Hepten-2-ol from Banana Fruit Using Multidimensional Gas Chromatography

Abstract

A polar fraction obtained from banana fruit pulp by high-vacuum distillation / solvent extraction (pentane-dichlorom ethane, 2 + 1) and subsequent liquid chromatography on silica gel was derivatized with isopropylisocyanate. Separation of enantiom ers of heptan-2-ol and Z-4-hepten-2-ol was performed via their carbamates by means of multidimensional gas chromatography using an achiral (D B -5, column 1) and a chiral (X E -60, column 2) capillary column. The enantiomeric ratios of heptan-2-ol and Z-4-hepten-2-ol were determ ined to be (/?)( - ) 39% and (S)( + ) 61% as well as (/? )(+ ) 26% and (S )(-) 74% , respectively. The absolute configuration of optically enriched ( 5 ) (-)-Z-4-hepten-2-ol was determined from its (R)-2-phenylpropionic acid ester by 1H NM R spectroscopy.