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J Chromatogr A. 1996 Jan 8;719(2):333-43.

Isolation and structural elucidation of the predominant geometrical isomers of alpha-carotene.

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Department of Food Science, North Carolina State University, Raleigh 27695-7624, USA.


The recent development and application of a polymeric C30 stationary phase have given unique separations of cis-trans carotenoid isomers in reversed-phase (RP) liquid chromatography (LC) owing to the exceptional shape selectivity of this stationary phase. In the present research, several geometrical isomers of alpha-carotene were at least partially resolved from a photo-isomerized mixture when chromatographed on a 3-microns polymeric C30 column. Double bond configurations of the five predominant alpha-carotene peaks, as isolated on a semi-preparative C30 column, were unambiguously assigned using 1H nuclear magnetic resonance (NMR) spectroscopy, giving the following order of elution: 13-cis, 13'-cis, all-trans, 9-cis, and 9'-cis geometrical forms. Electronic absorption spectra for these isomers were in agreement with the identification of peaks. The alpha-carotene isomers separated and identified herein had not been previously resolved in RPLC. Confirmation of the structures of geometrical alpha-carotene isomers will aid further studies on the possible physiological roles of these compounds in biological tissues.

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