1638-05-7Relevant articles and documents
Isolation by high-pressure liquid chromatography of cis-trans isomers of β-apo-12'-carotenal and determination of their configurations by 1H NMR spectroscopy
Hu, Ying,Mizoguchi, Tadashi,Kurimoto, Yoshitaka,Koyama, Yasushi
, p. 1949 - 1958 (1995)
High pressure liquid chromatography of an isomeric mixture of β-apo-12'-carotenal, which was obtained by iodine-sensitized photo-isomerization, resolved eleven peaks of cis-trans isomers.The configurations of eight isomers, i.e., all-trans, 9-, 13-, 15-, 13'-mono-cis, and 9,13-, 9,13'- and 13,13'-di-cis, were determined by 1H NMR spectroscopy. 1H,1H COSY and long-range 1H,1H COSY spectra was used for the assignments of all the 1H signals.The isomerization shifts of the olefinic 1H signals and the NOE correlations, which were idenfied in the 1H,1H NOESY spectra, were used for the configurational determinations.In relation to the difference in isomeric composition between retinoids and carotenoids, the cis configurations found in the present compound (C25 aldehyde) are compared with those found in retinal (C20 aldehyde) and β-apo-8'-carotenal (C30 aldehyde) having a shorter and a longer conjugated chain, respectively.
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
Total Synthesis of Acetylenic Carotenoids. 2. Synthesis of (all-E)-(3R,3'R)-Diatoxanthin and (all-E)-(3R)-7,8-Didehydrocryptoxanthin
Haugan, Jarle Andre,Liaaen-Jensen, Synnoeve
, p. 899 - 904 (2007/10/02)
Optically active (all-E)-(3R,3'R)-diatoxanthin, indistinguishable from the natural carotenol, has been prepared by total synthesis for the first time with 34percent overall yield in four steps from the available (2E)-5-(4R)-4-hydroxy-2,6,6-trimethylcyclo
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.
Polyunsaturated aldehydes by direct polyvinylogation of carbonyl compounds using functionalized phosphonates.
Duhamel, Lucette,Guillemont, Jerome,Gallic, Yann Le,Ple, Gerard,Poirier, Jean-Marie,et al.
, p. 3129 - 3132 (2007/10/02)
Carbonyl compounds are converted into polyethylenic aldehydes in a one pot reaction with the anions of phosphonates 1. followed by a mild acidic hydrolysis.
Synthese von optisch aktiven, natuerlichen Carotinoiden und strukturell verwandten Naturprodukten. IX. Synthese von (3R)-Hydroxyechinenon, (3R,3'R)- und (3R,3'S)-Adonixanthin, (3R)-Adonirubin, deren optischen Antipoden und verwandten Verbindungen
Bernhard, Kurt,Englert, Gerhard,Mayer, Hans,Mueller, Robert K.,Ruettimann, August,et al.
, p. 2469 - 2484 (2007/10/02)
The synthesis of racemic and optically active hydroxyechinenone (12-14), adonixanthin (16-19), adonirubin (22-24), meso-astaxanthin (26) and their corresponding diosphenols (15, 20, 21, 25, 27, 28, and 29) by Wittig reaction is reported, starting from suitable C15-phosphonium salts and C10-aldehydes.
