60046-54-0Relevant articles and documents
Chemoenzymatic Synthesis of all-trans-Isomers of Lutein and Zeaxanthin
Kuregyan, A. G.,Oganesyan, E. T.,Pechinsky, S. V.
, p. 1674 - 1679 (2021/11/01)
Abstract: A method for the synthesis of all-trans-isomers of lutein and zeaxanthin has been proposed, which includes the stage of esterification of lutein and zeaxanthin with benzoic acid in the presence of enantioselective lipase Novozyme 435. Further hydrolysis of lutein and zeaxanthin dibenzoates has led to the formation of the initial xanthophylls in the all-trans configuration.
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
Rodríguez-DeLeón, Eloy,Jiménez-Halla, Oscar J.C.,Báez, José E.,Moustapha Bah
supporting information, (2019/04/30)
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
Process or synthesis of (3S)- and (3R)-3-hydroxy-beta-ionone, and their transformation to zeaxanthin and beta-cryptoxanthin
-
Page/Page column 28, (2012/07/27)
Disclosed is a process for the synthesis of (3R)-3-hydroxy-β-ionone and its (3S)-enantiomer in high optical purity from commercially available (rac)-α-ionone. The key intermediate for the synthesis of these hydroxyionones is 3-keto-α-ionone ketal that was prepared from (rac)-α-ionone after protection of this ketone as a 1,3-dioxolane. Reduction of 3-keto-α-ionone ketal followed by deprotection, lead to 3-hydroxy-α-ionone that was transformed into (rac)-3-hydrox-β-ionone by base-catalyzed double bond isomerization in 46% overall yield from (rac)-α-ionone. The racemic mixture of these hydroxyionones was then resolved by enzyme-mediated acylation in 96% ee. (3R)-3-Hydroxy-β-ionone and its (3S)-enantiomer were respectively transformed to (3R)-3-hydroxy-(β-ionylideneethyl)triphenylphosphonium chloride [(3R)-C15-Wittig salt] and its (3S)-enantiomer [(3S)-C15-Wittig salt] according to known procedures. Double Wittig condensation of these Wittig salts with commercial available 2,5- dimethtylocta-2,4,6-triene-1,8-dial provided all 3 stereoisomers of zeaxanthin. Similarly, (3R)-C15-Wittig and its (3S)-enantiomer were each coupled with β-apo-12′-carotenal.