58526-50-4Relevant articles and documents
Synthesis of 9-cis-retinoic acid and C-20-[3H3C]-9-cis-retinoic acid with high specific activity
Tadikonda, Praveen K.,Lacy, James M.,Rigdon, Michael G.,Deluca, Hector F.
, p. 1 - 10 (2007/10/03)
The synthesis of 9-cis-retinoic acid starting from 2,2,6-trimethylcyclohexanone is described. The same methodology was extended for the synthesis of deuterium and tritium labeled 9-cis-retinoic acid with high specific activity (73 Ci/mmol). In this methodology, a Grignard reaction was utilized for introducing three tritium atoms simultaneously in the final synthetic steps.
SYNTHETIC INVESTIGATIONS IN THE CHEMISTRY OF POLYENE COMPOUNDS LII. SYNTHESIS OF RETINOIC AND DIHYDRORETINOIC ESTERS BY THE REFORMATSKII REACTION
Tutorskaya, O. O.,Miropol'skaya, M. A.,Samokhvalov, G. I.
, p. 1237 - 1240 (2007/10/02)
The esters of 7,8- and 7,14-dihydroretinoic acids were obtained by the reaction of 6-methyl-8-(2,6,6-trimethyl-1-cyclohexenyl)-3,5-octadien-2-one with bromoacetic ester in the Reformatskii reaction followed by dehydration.The 7,8- and 7,14-dihydroretinoic
Assignment of 1H and 13C NMR Spectra of Retinoic Acid Ester Isomers Observed in the Long-Wavelength UV-Induced Photostationary State
Curley, Robert W.,Fowble, John W.
, p. 707 - 709 (2007/10/02)
1H and 13C chemical shift assignments, obtained with the aid of two-dimensional hetenuclear shift correlation and double-quantum coherence 13C-INADEQUATE experiments, are reported for four retinoic acid ester isomers observed at the photostationary state.Also detailed are 1H assignments for three additional isomers obtained in insufficient amounts for 13C measurements.KEY WORDS - Retionic acid esters Isomer identification 1H-13C correlation spectra 13C-INADEQUATE experiment
NEW MASKED BUILDING BLOCK FOR ISOPRENOID POLYENE CHAIN SYNTHESIS
Mandai, T.,Iuchi, Y.,Suzuki, K.,Kawada, M.,Otera, J.
, p. 4721 - 4724 (2007/10/02)
The new building blocks 2, 3, and 4 have been effectively synthesized starting from 2-hydroxymethyl-4-phenylthio-1-butene (1a).A convenient synthesis of retinoic acid methyl ester (9) using 2 is also described.
Transient Phenomena in the Pulse Radiolysis of Retinyl Polyenes. 1. Radical Anions
Raghavan, N.V.,Das, P.K.,Bobrowski, K.
, p. 4569 - 4573 (2007/10/02)
The spectra and kinetics of formation and decay of radical anions of a number of retinyl polyenes have been studied in methanol and 2-propanol at room temperature, using pulse radiolysis and kinetic spectrophotometry.The bimolecular rate constants for the attachment of solvated electrons, e-MeOH, to the retinyl polyenes are in the diffusion-controlled limit (8.6 x 109-1.6 x 1010 M-1 s-1).The radical anions of retinol and retinol acetate have their spectral maxima at 370-390 nm, and undergo decay very slowly with second-order kinetics.On the other hand, the radical anions of retinal, retinal n-butylamine Schiff base, and retinoic acid/ester have spectral maxima at 430-510 nm, and decay by first-order kinetics in methanol with rate constants in the range 1 x 104-1 x 106 s-1.The decay rates of radical anions of retinal and retinoic acid/ester become considerably longer on going from methanol to less acidic alcohol, 2-propanol, suggesting that protonation by solvent is the major mode of their decay in protic media.In the case of retinal Schiff base, an additional slow process with bimolecular rate constant 9.0 x 107 M-1 s-1 im methanol is observed for the formation of radical anion and is ascribed to the electron-transfer reaction from the methanol radical, .CH2OH.
