79985-66-3Relevant academic research and scientific papers
SYNTHETIC INVESTIGATIONS IN THE CHEMISTRY OF POLYENE COMPOUNDS. -- XLVIII. STRUCTURE AND TRANSFORMATIONS OF 12-CARBOXYRETINOIC ACIDS AND THEIR ESTERS. SYNTHESIS OF 13-CIS-RETINOIC ACID
Polyachenko, L. N.,Davydova, L. P.,Darskaya, E. N.,Filippova, T. M.,Samokhvalov, G. I.
, p. 685 - 694 (2007/10/02)
In reaction with ethyl β-methylglutaconate under the influence of alkali in methanol the Z and E isomers of β-ionylideneacetaldehyde form isomeric 9Z,11Z,13Z- and 9E,11Z,13Z-12-carboxyretinoic acids.Decarboxylation of the latter in the pyridine-piperidine system in the presence of copper salts leads to 13Z-retinoic acid and is accompanied by the formation of 9,13-dimethyl-7-(1,1,5-trimethyl-5-cyclohexen-6-yl)-7,9,11,13-octatetraene.The stereoisomeric transformations of 12-substituted 9E,Z,11Z,13Z-retinoic acids and the corresponding diols and diacetates obtained from them were investigated.Isomerization takes place at the double bond at the C9 atom and depends on the nature of the substituent at the C12 atom.
12-Carboxyretinoic Acids. Synthesis and Structure
Lewin, Anita H.,Whaley, M. Glenn,Parker, Steven R.,Carroll, F. Ivy
, p. 1799 - 1807 (2007/10/02)
Four isomeric 12-carboxyretinoic acids and their dimethyl esters (trans, 13-cis, 11-cis, and 11-cis,13-cis), along with two isomeric retinoic anhydrides (13-cis and 11-cis,13-cis), have been prepared and fully characterized.The primary product of the base-promoted condensation of trans-(β-ionylidene)acetaldehyde and β-methylglutaconate has been shown to be the 11-cis,13-cis-diacid.The interconversions and relative stabilities of these retinoids are discussed in terms of their conformations
