Solvent effects on the time-dependent photoisomerization of methyl retinoate.
The photoisomerization of methyl all-trans-retinoate is dependent upon both solvent polarity and irradiation time. The all-trans-isomer isomerizes most rapidly in solvents of high polarity. Methyl 11-cis-retinoate is maximally produced after three hours in dimethyl sulfoxide, while it is not formed to an appreciable extent in heptane. Methyl 13-cis-retinoate forms maximally after two hours in heptane, then decrease in concentration by one-half to about the same level maximally formed in dimethyl sulfoxide. The solvent and time dependences of the other isomers are presented to allow selection of conditions for maximal production of desired isomers. The results for methyl retinoate appear applicable for retinoic acid.
D002625:Chemistry, Organic; D007536:Isomerism; D007700:Kinetics; D055601:Organic Chemistry Phenomena; D012997:Solvents; D014212:Tretinoin / Q000031:analogs & derivatives*
D012997:Solvents; D014212:Tretinoin; C026296:methyl retinoate