69575-84-4

Upstream product

• 29706-61-4 9-cis-13-demethyl-retinal 
• 24336-20-7 7-methyl-9-(2,6,6-trimethylcyclohex-1-enyl)nona-2,4,6,8-tetraenal 
• 62285-98-7 5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide 

Downstream Products

• 24336-20-7 7-methyl-9-(2,6,6-trimethylcyclohex-1-enyl)nona-2,4,6,8-tetraenal 

Relevant academic research and scientific papers

Preparation of 11,14-epoxy-bridged and isomeric chain-demethylated retinals. 13-Demethyl-11,14-epoxy-, 9-demethyl-, 13-demethyl- and 9,13-bisdemethyl-retinals

9-Cis- and all-trans-13-demethyl-11,14-epoxyretinyl acetate were prepared via a Wittig coupling between β-ionylidenetriphenylphosphonium bromide (1) and 5-(acetoxymethyl)furfural.Saponification of these acetates, subsequent oxidation and HPLC separation a

Photochemistry of Linear Polyenes Related to Vitamin A. 13-Demethylretinal and 14-Methylretinal

The photochemistry of all-trans-13-demethylretinal (2) and all-trans-14-methylretinal (3) is examined in nonpolar and polar solvents.Upon extended irradiation into the first adsorption band, a photoequilibrium mixture is established that contains a number of isomeric photoproducts.High pressure liquid chromatographic methods are employed to isolate and purify each reaction product, and their adsorption spectral and photochemical properties are examined.Primary photoproducts and quantum yields (ψPI of trans -> cis or cis -> trans photoisomerization for all-trans-, 7-cis-, 9-cis-, and 11-cis-13- demethylretinal and all-trans-, 9-cis-, 11-cis-, and 13-cis-14-methylretinal are determined in a nonpolar solvent.The variation in ψPI and the relative photoproduct ratios of the isomers of 13-demethylretinal and 14-methylretinal differ from those of the corresponding isomers of retinal.The differences in quantum yields, primary products, and their relative ratios are analyzed in terms of the structural changes resulting from incorporation or removal of the alkyl substituent of the C-13-C-14 carbon-carbon double bond.

On the photoisomerisation of 13-desmethyl-retinal

All mono-cis-isomers of 13-desmethyl-retinal have been prepared fro the alll-trans-compound by photoisomerisation. The various isomers were separated by HPLC and identified by their 400 MHz-1NMR-spectra.