640-49-3Relevant academic research and scientific papers
Synthetic method of beta-apo-8'-carotenoic ethyl ester
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Paragraph 0039-0040; 0049-0050; 0059-0060; 0071, (2021/10/20)
The invention relates to the technical field of feed additives, and discloses a synthesis method of beta-apo-8'-carotenoic ethyl ester. According to the invention, beta-apo-8'-carotenoic ethyl ester is synthesized through a route of C10 + C2-> C12, C12 + C15-> C27, and C27 + C3-> C30, wherein in the route, C10 dialdehyde, vinyl ether (R is alkyl), C15 triphenyl phosphonium salt (X is Br or Cl) and ethoxyformyl ethylidene triphenylphosphine which are used as reactants are rich in source and low in cost, Vitamin A with high raw material cost does not need to be used, purification steps in the synthesis process are few, and operation is simple, so that the synthesis route is low in industrialization difficulty, large-scale production is easy to achieve, and the production cost of the beta-apo-8'-carotenoic ethyl ester is reduced.
Kinetics of β-Carotene Oxidation in the Presence of Highly Active Forms of μ-Carbido Diiron(IV) Tetraphenylporphyrinate
Simonova,Zaitseva,Tyulyaeva, E. Yu.,Zdanovich,Koifman
, p. 2128 - 2134 (2018/10/24)
Abstract: The oxidative destruction of β-carotene in the presence of highly oxidized forms of μ-carbido-bis[(5,10,15,20-tetraphenyl-21H,23H-porphyrinato)iron(IV)] (1 → 3) or its analog with axially coordinated imidazole (2 → 4) obtained under the action of tert-butyl hydroperoxide tBuOOH was studied by spectrophotometry. It was found that compound 3 is the oxo form of compound 1 singly oxidized at the macrocyclic ligand (π radical cation) under the action of which β-carotene is oxidized with a rate constant k = 3.3 L2 mol–2 s–1. A?conclusion is drawn that short-lived compound 4 has unique EAS and is capable of oxidizing tBuOOH to form O2, which makes it possible to consider it the model of peroxidase. The value of k for the reaction with the participation of β-carotene and compound 4 (k = 10.3 L2 mol–2 s–1) is three times higher than that with the participation of compound 3. If a new portion of β-carotene is added, the process of its oxidative destruction in the presence of compounds 3 or 4 occurs without additives of the dimeric complex and peroxide. A?possible nature of compound 4 is discussed, as well as the influence of N-base in the coordination sphere of the complex on the nature of active intermediates and the rate of β-carotene decomposition.
Synthesis of apocarotenoids by acyclic cross metathesis and characterization as substrates for human retinaldehyde dehydrogenases
Domínguez, Marta,Pequerul, Raquel,Alvarez, Rosana,Giménez-Dejoz, Joan,Birta, Eszter,Porté, Sergio,Rühl, Ralph,Parés, Xavier,Farrés, Jaume,de Lera, Angel R.
, p. 2567 - 2574 (2018/04/19)
A new synthesis of three apocarotenoids, namely 14′-apo-β-carotenal, 12′-apo-β-carotenal and 10′-apo-β-carotenal, has been achieved that is based on the acyclic cross-metathesis of the hexaene derived from retinal and the corresponding partners. These compounds can be enzymatically converted to their carboxylic acids by the human aldehyde dehydrogenases involved in retinaldehyde oxidation. Their kinetic parameters suggest that these enzymes might play a role in the physiological metabolism of apocarotenoids.
Synthesis of all-trans-[10′-3H]-8′-apo-β-carotenoic acid
Reddy, Pulgam Veera,Rabago-Smith, Monsterrat,Borhan, Babak
, p. 79 - 89 (2007/10/03)
The enzyme, 15, 15′-β-carotene dioxygenase (BCDOX), facilitates the oxidation of β-carotene to yield retinal. This is a remarkable process in which one of 11 double bonds in β-carotene is selectively oxidized. To further probe the mechanistic aspects of BCDOX, the synthesis of all-trans-[10′-3H]-8′-apo-β-carotenoic acid is reported. This compound will be used as a photoaffinity labeling reagent to probe the β-carotene binding pocket within BCDOX. The synthesis outlines a simple and efficient route for the incorporation of tritium at the 10′ olefinic carbon of 8′-apo-β-carotenoic acid. Copyright
Oxidative degradation of β-carotene and β-apo-8′-carotenal
Mordi, Raphael C.,Walton, John C.,Burton, Graham W.,Hughes, Lise,Ingold U., Keith,Lindsay A., David,Moffatt J., Douglas
, p. 911 - 928 (2007/10/02)
In the self-initiated oxidation of β-carotene with molecular oxygen the rate of oxygen uptake was shown to depend on the oxygen partial pressure. Epoxides, dihydrofurans, carbonyl compounds, carbon dioxide, oligomeric material, traces of alcohols, and probably carboxylic acids were formed. The main products in the early stage of the oxidation were shown to be 5,6-epoxy-β-carotene. 15,15′-epoxy-′-carotene, diepoxides, and a series of β-apo-carotenals and -carotenones. As the oxidation proceeded uncharacterised oligomeric material and the carbonyl compounds became more important and the epoxides degraded. In the final phase of the oxidation the longer chain β-apo-carotenals were themselves oxidized to shorter chain carbonyl compounds, particularly β-apo-13-carotenone, β-ionone, 5,6-epoxy-gb-ionone, dihydroactinidiolide and probably carboxylic acids. The effect of iron, copper and zinc stearates on the product composition and proportions was studied, as was the effect of light. The oxidation was inhibited by 2,6-di-t-butyl-4-methyphenol and α-tocopherol. The oxidations of β-apo-8′-carotenal and retinal under similar conditions were studied briefly, and the main products from the former compound were characterized. The initiation, the formation of the epoxides, the β-apo-carotenals and -carotenones, the successive chain shortening of the aldehydes to the ketones, and the formation of dihydroactinidiolide are explained in terms of free radical peroxidation chemistry.
Efficient oxidation of β?carotene in μ-carbido diiron octapropyltetraazaporphyrin–tBuOOH system
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, (2019/05/29)
The oxidative decomposition of β?carotene mediated by μ-carbido diiron octapropyltetraazaporphyrin ([FeOPrTAP]2C)–tBuOOH system was investigated in benzene. Interaction between tBuOOH and the binuclear complex resulted in the generation of powerful high-oxidized species those are capable of oxidizing the employed substrate within the limits of several minutes. The explanation for such reactivity behavior involves the existence of a mixture of reactive intermediates in the reaction medium: more stable singly oxidized at the macrocyclic ligand π-cation radical as well as much more reactive dication species that is more contributing to the reaction rate. The introduction of imidazole into the coordination sphere of the initial diiron complex accelerates the β?carotene destruction because of generation of a powerful high-oxidizing species, which is capable of oxidizing β?carotene as well as the applied organic peroxide resulting in dioxygen release. Catalytic behavior of all the observed active intermediates was supported by recycling of the reaction under carotene adding. The quantitative characteristics of reactivity of studied systems were obtained and the possible reaction mechanisms were proposed.
