31272-50-1Relevant 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
Bidirectional Hiyama–Denmark Cross-Coupling Reactions of Bissilyldeca-1,3,5,7,9-pentaenes for the Synthesis of Symmetrical and Non-Symmetrical Carotenoids
Rivas, Aurea,Pérez-Revenga, Víctor,Alvarez, Rosana,de Lera, Angel R.
, p. 14399 - 14407 (2019/11/03)
The construction of the carotenoid skeleton by Pd-catalyzed Csp2?Csp2 cross-coupling reactions of symmetrical and non-symmetrical 1,10-bissilyldeca-1,3,5,7,9-pentaenes and the corresponding complementary alkenyl iodides has been developed. Reaction conditions for these bidirectional and orthogonal Hiyama–Denmark cross-coupling reactions of bisfunctionalized pentaenes are mild and the carotenoid products preserve the stereochemical information of the corresponding oligoene partners. The carotenoids synthesized in this manner include β,β-carotene and (3R,3′R)-zeaxanthin (symmetrical) as well as 9-cis-β,β-carotene, 7,8-dihydro-β,β-carotene and β-cryptoxanthin (non-symmetrical).
RPE65 has an additional function as the lutein to meso-zeaxanthin isomerase in the vertebrate eye
Shyam, Rajalekshmy,Gorusupudi, Aruna,Nelson, Kelly,Horvath, Martin P.,Bernstein, Paul S.
, p. 10882 - 10887 (2017/10/13)
Carotenoids are plant-derived pigment molecules that vertebrates cannot synthesize de novo that protect the fovea of the primate retina from oxidative stress and light damage. meso-Zeaxanthin is an ocular-specific carotenoid for which there are no common
Synthesis of (3 R,3 R)-zeaxanthin and its meso -stereoisomer from (3 R,3 R,6 R)-lutein via (3 R)-3,4-anhydrolutein
Khachik, Frederick
experimental part, p. 453 - 459 (2012/03/27)
A process has been developed for the partial synthesis of (3R,3R)-zeaxanthin and (3R,3S; meso)-zeaxanthin from commercially available (3R,3R,6R)-lutein. This involves the regioselective hydroboration of a dehydration product of lutein, namely (3R)-3,4-didehydro-,-caroten-3-ol [(3R)-3,4-anhydrolutein], to yield a mixture of (3R,3R)-zeaxanthin and (3R,3S; meso)-zeaxanthin followed by separation of these carotenoids by enzyme-mediated acylation. (3R,3R,6R)-Lutein, (3R,3R)-zeaxanthin and its meso-isomer accumulate in human ocular tissues and have been implicated in the prevention of age-related macular degeneration (AMD). Georg Thieme Verlag Stuttgart New York.
Process or synthesis of (3S)- and (3R)-3-hydroxy-beta-ionone, and their transformation to zeaxanthin and beta-cryptoxanthin
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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.
Synthesis of C40-symmetrical fully conjugated carotenoids by olefin metathesis
Fontan, Noelia,Dominguez, Marta,Ulvarez, Rosana,De Lera, Ungel R.
experimental part, p. 6704 - 6712 (2012/01/03)
In an effort to push olefin metathesis to the limits of conjugation in reactants and products, the C40-symmetrical carotenoids β,β-carotene (1), lycopene (2), (3R,3′R)-zeaxanthin (3), and rac-isozeaxanthin (4), which are conjugated undecaenes, have been synthesized from C21-terminal hexaenes by treatment with Grubbs' second-generation Ru catalyst in dichloromethane at 50 °C.
Fast regeneration of carotenoids from radical cations by isoflavonoid dianions: Importance of the carotenoid keto group for electron transfer
Han, Rui-Min,Chen, Chang-Hui,Tian, Yu-Xi,Zhang, Jian-Ping,Skibsted, Leif H.
scheme or table, p. 126 - 132 (2010/05/11)
Electron transfer to radical cations of β-carotene, zeaxanthin, canthaxanthin, and astaxanthin from each of the three acid/base forms of the diphenolic isoflavonoid daidzein and its C-glycoside puerarin, as studied by laser flash photolysis in homogeneous methanol/chloroform (1/9) solution, was found to depend on carotenoid structures and more significantly on the deprotonation degree of the isoflavonoids. None of the carotenoid radical cations reacted with the neutral forms of the isoflavonoids while the monoanionic and dianionic forms of the isoflavonoids regenerated the oxidized carotenoid. Electron transfer to the β-carotene radical cation from the puerarin dianion followed second order kinetics with the rate constant at 25 °C k2 = 5.5 × 109 M-1 s-1, zeaxanthin 8.5 × 109 M-1 s-1, canthaxanthin 6.5 × 1010 M-1 s-1, and astaxanthin 11.1 × 1010 M-1 s-1 approaching the diffusion limit and establishing a linear free energy relationship between rate constants and driving force. Comparable results found for the daidzein dianion indicate that the steric hindrance from the glucoside is not important suggesting the more reducing but less acidic 4′-OH/4′-O- as electron donors. On the basis of the rate constants obtained from kinetic analyses, the keto group of carotenoids is concluded to facilitate electron transfer. The driving force was estimated from oxidation potentials, as determined by cyclic-voltametry for puerarin and daidzein in aqueous solutions at varying pH conditions, which led to the standard reduction potentials E° = 1.13 and 1.10 V versus NHE corresponding to the uncharged puerarin and daidzein. For pH > pka2, the apparent potentials of both puerarin and daidzein became constants and were E° = 0.69 and 0.65 V, respectively. Electron transfer from isoflavonoids to the carotenoid radical cation, as formed during oxidative stress, is faster for astaxanthin than for the other carotenoids, which may relate to astaxanthins more effective antioxidative properties and in agreement with the highest electron accepting index of astaxanthin.
MICRONIZED CAROTENOID PREPARATION AS IMMUNOSTIMULANT FOR CRUSTACEANS
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Page/Page column 7; 8, (2010/09/17)
The present invention refers to micronized carotenoids in an oily carrier; the composition acts as immunostimulant for crustaceans.
Process for Synthesis of (3R,3'R)-Zeaxanthin and (3R,3'S;meso)-Zeaxanthin from (3R,3'R,6'R)-Lutein via (3R)-3',4'-Anhydrolutein
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Page/Page column 9, (2009/10/01)
(3R, 3′R, 6′R)-Lutein and (3R, 3′R)-zeaxanthin are two dietary carotenoids that are present in most fruits and vegetables commonly consumed in the US and accumulate in the human plasma, major organs, and ocular tissues. Another stereoisomer of (3R, 3′R)-zeaxanthin that is not of dietary origin but is found in the human ocular tissues is (3R, 3′S; meso)-zeaxanthin. There is growing evidence that these carotenoids play an important role in the prevention of age-related macular degeneration (AMD) that is the leading cause of blindness in the U.S. and the Western World. In view of the potential therapeutic application of dietary lutein, (3R, 3′R)-zeaxanthin, and (3R, 3′S; meso)-zeaxanthin, the industrial production of these carotenoids is of considerable importance. The present invention provides a process for the partial synthesis of (3R, 3′R)-zeaxanthin and (3R, 3′S; meso)-zeaxanthin from a readily accessible dehydration product of (3R, 3′R, 6′R)-lutein, namely, (3R)-3′,4′-didehydro-β,β-caroten-3-ol [(3R)-3′,4′-anhydrolutein]. The process involves regioselective hydroboration of (3R)-3′,4′-anhydrolutein to a mixture of (3R, 3′R)-zeaxanthin and (3R, 3′S; meso)-zeaxanthin followed by separation of these carotenoids by enzyme-mediated acylation.
