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Article

A Simple and Efficient Method for the Partial Synthesis of Pure (3R,3’S)-Astaxanthin from (3R,3’R,6’R)-Lutein and Lutein Esters via (3R,3’S)-Zeaxanthin and Theoretical Study of Their Formation Mechanisms

1
Posgrado en Ciencias Químico Biológicas, Faculty of Chemistry, Autonomous University of Querétaro, Querétaro 76010, Mexico
2
Department of Chemistry, Division of Natural and Exact Sciences, University of Guanajuato, Guanajuato 36050, Mexico
*
Authors to whom correspondence should be addressed.
Academic Editor: Vincenzo Piccialli
Molecules 2019, 24(7), 1386; https://doi.org/10.3390/molecules24071386
Received: 26 March 2019 / Revised: 6 April 2019 / Accepted: 7 April 2019 / Published: 9 April 2019
(This article belongs to the Special Issue New Studies on the Synthesis of Biologically Active Products)
Carotenoids are natural compounds that have important roles in promoting and maintaining human health. Synthetic astaxanthin is a highly requested product by the aquaculture industry, but natural astaxanthin is not. Various strategies have been developed to synthesize this carotenoid. Nonetheless, these approaches have not only provided limited global yields, but its main commercial source also carries several health risks for humans. In this contribution, the one-pot base-catalyzed reaction of (3R,3’R,6’R)-lutein (1) esters has resulted in a successful isomerization process to easily obtain up to 95% meso-zeaxanthin (2), which in turn is oxidized to (3R,3’S)-astaxanthin (3) with a global yield of 68%. The same oxidation performed with UV irradiation (365 nm) for 5 min provided the highest global yield (76%). These chemical transformations have also been achieved with a significant reduction of the health risks associated with its potential human consumption. Furthermore, this is the first time only one of the configurational isomers has been obtained semisynthetically. The poorly understood formation mechanisms of these two compounds were also investigated using Density-Functional Theory (DFT) calculations. These theoretical studies revealed that the isomerization involves a base-catalyzed deprotonation at C-6’, followed by C-4’ protonation, while the oxidation occurs via free radical mechanisms. View Full-Text
Keywords: carotenoids; meso-zeaxanthin; (3R,3’S)-astaxanthin; partial synthesis; DFT calculation; reaction mechanism carotenoids; meso-zeaxanthin; (3R,3’S)-astaxanthin; partial synthesis; DFT calculation; reaction mechanism
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MDPI and ACS Style

Rodríguez-deLeón, E.; Jiménez-Halla, J.O.C.; Báez, J.E.; Bah, M.M. A Simple and Efficient Method for the Partial Synthesis of Pure (3R,3’S)-Astaxanthin from (3R,3’R,6’R)-Lutein and Lutein Esters via (3R,3’S)-Zeaxanthin and Theoretical Study of Their Formation Mechanisms. Molecules 2019, 24, 1386. https://doi.org/10.3390/molecules24071386

AMA Style

Rodríguez-deLeón E, Jiménez-Halla JOC, Báez JE, Bah MM. A Simple and Efficient Method for the Partial Synthesis of Pure (3R,3’S)-Astaxanthin from (3R,3’R,6’R)-Lutein and Lutein Esters via (3R,3’S)-Zeaxanthin and Theoretical Study of Their Formation Mechanisms. Molecules. 2019; 24(7):1386. https://doi.org/10.3390/molecules24071386

Chicago/Turabian Style

Rodríguez-deLeón, Eloy, J. O.C. Jiménez-Halla, José E. Báez, and M. M. Bah 2019. "A Simple and Efficient Method for the Partial Synthesis of Pure (3R,3’S)-Astaxanthin from (3R,3’R,6’R)-Lutein and Lutein Esters via (3R,3’S)-Zeaxanthin and Theoretical Study of Their Formation Mechanisms" Molecules 24, no. 7: 1386. https://doi.org/10.3390/molecules24071386

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