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

Journal of Chromatography. a
C EmenhiserS J Schwartz

Abstract

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.

References

May 11, 1984·Science·G W Burton, K U Ingold

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Citations

Oct 13, 2014·Food Chemistry·Heliofabia Virginia De Vasconcelos FacundoBeatriz Rosana Cordenunsi
Apr 14, 2015·Free Radical Research·H StutzP M Eckl
Jan 10, 2012·Journal of Chromatography. a·S M Rivera, R Canela-Garayoa
Jun 1, 2010·Analytica Chimica Acta·François BretonJanusz Pawliszyn
Apr 29, 2006·Magnetic Resonance in Chemistry : MRC·M L Miglietta, R Lamanna
May 17, 2006·Journal of Chromatography. a·Kerry L TaylorAnita Oberholster
Feb 14, 2006·Journal of Chromatography. a·Gokulakrishnan SrinivasanKlaus Müller
Sep 9, 2005·Journal of Pharmaceutical and Biomedical Analysis·A Marín, C Barbas
Dec 17, 2014·Journal of Photochemistry and Photobiology. B, Biology·Dajing LiChunquan Liu
Aug 3, 2006·Journal of Agricultural and Food Chemistry·Stefano TizianiYael Vodovotz
Jul 25, 2000·Journal of Chromatography. a·J Oliver, A Palou
Jul 13, 2000·Journal of Chromatography. a·L C SanderM Pursch
Jun 15, 1997·Analytical Chemistry·D J AndersonK A Davis
Oct 2, 2003·Journal of Agricultural and Food Chemistry·Ashley A Updike, Steven J Schwartz
May 29, 2007·Journal of Agricultural and Food Chemistry·Veridiana V de Rosso, Adriana Z Mercadante
Feb 3, 2005·Journal of Agricultural and Food Chemistry·Karsten PutzbachGregory G Dolnikowski

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