472-86-6Relevant articles and documents
Inoue et al.
, p. 265 (1979)
Activation Barriers for the Trans -> Cis Photoisomerization of all-trans-Retinal
Waddell, Walter H.,Chihara, Kohji
, p. 7389 - 7390 (1981)
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A porous coordination network catalyzes an olefin isomerization reaction in the pore
Ohara, Kazuaki,Kawano, Masaki,Inokuma, Yasuhide,Fujita, Makoto
, p. 30 - 31 (2010)
(Figure Presented) All-trans retinal efficiently diffused into the pore of a porous coordination network consisting of ZnI2 and an electron-deficient triazine-cored ligand. Enclathrated retinal was isomerized into the 13-cis form and easily replaced with all-trans retinal in solution, thus revealing the catalysis of retinal isomerization by the porous network.
Z -isomerization of retinoids through combination of monochromatic photoisomerization and metal catalysis
Kahremany, Shirin,Sander, Christopher Lane,Tochtrop, Gregory P.,Kubas, Adam,Palczewski, Krzysztof
supporting information, p. 8125 - 8139 (2019/09/19)
Catalytic Z-isomerization of retinoids to their thermodynamically less stable Z-isomer remains a challenge. In this report, we present a photochemical approach for the catalytic Z-isomerization of retinoids using monochromatic wavelength UV irradiation treatment. We have developed a straightforward approach for the synthesis of Z-retinoids in high yield, overcoming common obstacles normally associated with their synthesis. Calculations based on density functional theory (DFT) have allowed us to correlate the experimentally observed Z-isomer distribution of retinoids with the energies of chemically important intermediates, which include ground- and excited-state potential energy surfaces. We also demonstrate the application of the current method by synthesizing gram-scale quantities of 9-cis-retinyl acetate 9Z-a. Operational simplicity and gram-scale ability make this chemistry a very practical solution to the problem of Z-isomer retinoid synthesis.
Efficient, low-cost synthesis of retinal (Vitamin A aldehyde)
Hruszkewycz, Damian P.,Cavanaugh, Kathryn R.,Takamura, Kathryn T.,Wayman, Lora M.,Curley Jr., Robert W.
experimental part, p. 2205 - 2207 (2011/09/14)
Inexpensive retinyl acetate has been subjected to transesterification followed by allylic oxidation to give retinal in 98% yield as a 92:8 mixture of all-trans/13-cis isomers after chromatographic separation. More convenient methods of isolating the all-trans isomer have also been employed. Georg Thieme Verlag Stuttgart ? New York.
