Preparation and Spectroscopic Characterization of 3'-Oxolutein

Peter Molnar; Jozsef Deli; Erzsebet Osz; Gyula Toth; Ferenc Zsila; Christian Herrero; John T. Landrum

doi:10.2174/157017806779025933

ISSN: 1570-1786
E-ISSN: 1875-6255

Preparation and Spectroscopic Characterization of 3'-Oxolutein
Authors: Peter Molnar¹, Jozsef Deli², Erzsebet Osz³, Gyula Toth⁴, Ferenc Zsila⁵, Christian Herrero⁶ and John T. Landrum⁷
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¹ Department of Biochemistry and Medical Chemistry, University of Pecs, Medical School, Szigeti ut 12. P.O. Box 99, H-7601 Pécs, Hungary. ² Department of Biochemistry and Medical Chemistry, University of Pecs, Medical School, Szigeti ut 12. P.O. Box 99, H-7601 Pécs, Hungary. ³ Department of Biochemistry and Medical Chemistry, University of Pecs, Medical School, Szigeti ut 12. P.O. Box 99, H-7601 Pécs, Hungary. ⁴ Department of Biochemistry and Medical Chemistry, University of Pecs, Medical School, Szigeti ut 12. P.O. Box 99, H-7601 Pécs, Hungary. ⁵ Department of Biochemistry and Medical Chemistry, University of Pecs, Medical School, Szigeti ut 12. P.O. Box 99, H-7601 Pécs, Hungary. ⁶ Department of Biochemistry and Medical Chemistry, University of Pecs, Medical School, Szigeti ut 12. P.O. Box 99, H-7601 Pécs, Hungary. ⁷ Department of Biochemistry and Medical Chemistry, University of Pecs, Medical School, Szigeti ut 12. P.O. Box 99, H-7601 Pécs, Hungary.
Source: Letters in Organic Chemistry, Volume 3, Issue 10, Oct 2006, p. 723 - 734
DOI: https://doi.org/10.2174/157017806779025933
- Available online: 01 Oct 2006

Abstract

In this study we report on the preparation of 3'-oxolutein (1) by MnO2- and NiO2-oxidation of lutein (2) and the complete structure elucidation of this carotenoid by spectroscopic (UV/VIS, IR, 1H-NMR, 13C-NMR, CD, MS) methods and chemical reaction (NaBH4 reduction). The complete assignment of the 13CNMR spectrum of this carotenoid will be presented for the first time. A new carotenoid with alternative structure (8) is the major product of NiO2-oxidation of lutein (2) and partial spectroscopic characterization supports a structural assignment in which the β-end group has undergone extensive oxidation with concomitant ring opening.

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2006-10-01

2025-09-15

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Article Type: Research Article

Keyword(s): 3'-oxolutein; Carotenoids; oxidation of lutein; spectroscopic characterization; stereochemistry; structure elucidation

Preparation and Spectroscopic Characterization of 3'-Oxolutein

Abstract

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