Chromatographic Separation of Vitamin E Enantiomers

Molecules. 2017 Feb 4;22(2):233. doi: 10.3390/molecules22020233.

Abstract

Vitamin E is recognized as an essential vitamin since its discovery in 1922. Most vegetable oils contain a mixture of tocopherols and tocotrienols in the vitamin E composition. Structurally, tocopherols and tocotrienols share a similar chromanol ring and a side chain at the C-2 position. Owing to the three chiral centers in tocopherols, they can appear as eight different stereoisomers. Plant sources of tocopherol are naturally occurring in the form of RRR while synthetic tocopherols are usually in the form of all-racemic mixture. Similarly, with only one chiral center, natural tocotrienols occur as the R-isoform. In this review, we aim to discuss a few chromatographic methods that had been used to separate the stereoisomers of tocopherols and tocotrienols. These methods include high performance liquid chromatography, gas chromatography and combination of both. The review will focus on method development including selection of chiral columns, detection method and choice of elution solvent in the context of separation efficiency, resolution and chiral purity. The applications for separation of enantiomers in vitamin E will also be discussed especially in terms of the distinctive biological potency among the stereoisoforms.

Keywords: Vitamin E; chromatography; enantiomers; tocopherols; tocotrienols.

Publication types

  • Review

MeSH terms

  • Chromatography* / methods
  • Chromatography, Gas
  • Chromatography, High Pressure Liquid
  • Molecular Structure
  • Stereoisomerism
  • Tocopherols / chemistry
  • Tocotrienols / chemistry
  • Vitamin E / chemistry*
  • Vitamin E / isolation & purification*

Substances

  • Tocotrienols
  • Vitamin E
  • Tocopherols