Countercurrent chromatographic isolation and purification of 11′-α-tocomonoenol from the vitamin E extract of palm oil. (1st August 2018)

• Record Type: Journal Article
• Authors: Müller, Marco; Hammann, Simon; Vetter, Walter
• Is Part Of: Food chemistry. Volume 256(2018)
• Page Start: 327
• Page End: 332
• Publication Date: 2018-08-01
• Subjects: Countercurrent chromatography -- Tocomonoenol -- Vitamin E -- Palm Oil -- GC/MS -- NMR spectroscopy; Food -- Analysis -- Periodicals; Food -- Composition -- Periodicals; 664
• DOI: 10.1016/j.foodchem.2018.02.133
• Languages: English
• ISSNs: 0308-8146

Abstract

Highlights: The new vitamin E compound α-tocomonoenol was isolated from a palm oil capsule. CCC followed by column chromatography provided 5.6 mg product with 99.5% purity. The structure was determined to be 11′-α-tocomonoenol by 1 H NMR spectroscopy. A general CCC elution profile was developed for vitamin E homologues. Abstract: A new vitamin E homologue, α-tocomonoenol was detected in palm oil, but was not isolated in large amounts and with high purity so far. Here we present an easy and fast method to isolate α-tocomonoenol from vitamin E rich nutrient capsules with countercurrent chromatography (CCC). With the solvent system n -hexane – benzotrifluoride – acetonitrile (10:3.5:6.5, v/v/v ) about 30 mg α-tocomonoenol with a purity of 75% could be enriched in one step from 1 g crude sample. Column chromatography with 20% deactivated silica gel and n -hexane – ethyl acetate (95:5, v/v ) was performed to gain 5.6 mg α-tocomonoenol with a purity of 99.5% according to GC/MS. Structural verification by 1 H NMR spectroscopy verified that the double bond was located in 11′-position (11′-α-tocomonoenol). The trace impurity detected in the isolate was identified to be 12′-α-tocomonoenol, a compound previously detected in marine samples.