Isolation and Structural Elucidation of Different Geometrical Isomers of Lycopene

Publication Type

Journal contribution

Authors

Fröhlich,K.; Conrad, J.; Schmid,A.; Breithaupt, D.E.; Böhm, V.

Year of publication

2007

Published in

Int. J. Vitam. Nutr. Res.

Band/Volume

77/6

Page (from - to)

369–375

Five geometrical isomers of lycopene were isolated from a photoisomerized mixture on a semi-preparative C₃₀ column and characterized by UV-vis spectroscopy, mass spectroscopy, and nuclear magnetic resonance (NMR) spectroscopy.
¹H NMR and 2D NMR measurements were used to unambiguously assign the double bondconfiguration of five isomers: (5Z,9’Z)-, (9Z)-, (5Z,9Z)-, (all-E)-, and (5Z)-lycopene.
This will allow other laboratories to use the results for their C₃₀ HPLC. In addition, it is possible to investigate structure-activity relationships for these lycopene isomers which will improve the understanding of their physiological role in biological tissues.