Enantiomeric resolution of (±)-licarin A by high-performance liquid-chromatography using a chiral stationary phase

J Chromatogr A. 2011 Sep 28;1218(39):7051-4. doi: 10.1016/j.chroma.2011.07.093. Epub 2011 Aug 6.

Abstract

(±)-Licarin A (1), a neolignan obtained by the oxidative coupling reaction of isoeugenol, had in this study its enantiomers resolved. A novel, quick and efficient enantiomeric resolution of 1 was directly performed by chiral high-performance liquid chromatography (HPLC-PDA) protocol (CHIRALPACK(®) AD column; 9:1 (v/v) n-hexane:2-propanol; 1.0 mL/min). This method provided a chromatogram profile with a well-resolved peak separation. After isolation of each enantiomer with ee>99.9%, they were analysed in a polarimeter. Compound 2, which showed a retention time (t(r)) of 12.13 min, was the (+)-enantiomer and compound 3 (t(r)=18.90 min) was the (-)-enantiomer.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 2-Propanol / chemistry
  • Amylose / analogs & derivatives
  • Amylose / chemistry
  • Chromatography, High Pressure Liquid / methods*
  • Eugenol / analogs & derivatives
  • Eugenol / chemistry
  • Hexanes / chemistry
  • Lignans / chemistry*
  • Lignans / isolation & purification
  • Phenylcarbamates / chemistry
  • Stereoisomerism

Substances

  • Hexanes
  • Lignans
  • Phenylcarbamates
  • dehydrodiisoeugenol
  • licarin A
  • Chiralpak AD
  • n-hexane
  • Eugenol
  • Amylose
  • 2-Propanol