Abstract:

The separation of racemic furaneol and homofuraneol by packed column supercritical fluid chromatography was
studied. First, on an analytical scale, the effects of chiral column type, modifier solvent type and modifier solvent content in
mobile phase, column temperature, column pressure and flow rate on capacity factor (k’), selectivity factor (α) and resolution
factor (Rs) were investigated. The optimum conditions for resoluting furanone were Chiralpak AD-H column, column
temperature of 30 ℃, column pressure of 10 MPa, 1.0% (V/V) methanol in mobile phase and flow rate of 1.5 mL/min,
whereby Rs was 1.54. The optimum conditions to resolute homofuraneol were Chiralpak AD-H column, column temperature
of 33 ℃, column pressure of 13 MPa, 1.5% (V/V) ethanol in mobile phase and flow rate of 1.5 mL/min, whereby Rs was
1.51. Second, experiments on a preparative scale were carried out under the above optimum conditions, and the enantiomers
of furaneol and homofuraneol were successfully obtained with a purity of no less than 90% as well as a recovery yield
of no less than 70%. The present work will be helpful for evaluating the potential applications of chiral furaneol or chiral
homofuraneol to enhance food flavor, where the enantiomers of furaneol and homofuraneol are prerequisite.

Key words: packed column super critical fluid chromatography, furaneol, homofuraneol, chiral preparative resolution, enantiomer