53121-26-9

Upstream product

• 65527-83-5 (E)-4-Acetoxy-2-methyl-2-butenal-1-diethylacetal 
• 138846-06-7 2-[(1’E,3’E)-3’-methyl-4’-iodobuta-1’,3’-dien-1’yl]-1,3,3-trimethylcyclohex-1-ene 
• 59057-30-6 (1E)-1-(2,6,6-trimethylcyclohex-1-enyl)-3-methyl-1,4-pentadien-3-ol 
• 26586-02-7 (E)-4-acetoxy-2-methylcrotonaldehyde 
• 17974-55-9 (2E,4E)-ethyl 3-methyl-5-(2,6,6-trimethylcyclohex-1-enyl)penta-2,4-dienoate 
• 3917-39-3 (2E,4E)-3-methyl-5-(2,6,6-trimethyl-1-cyclohexenyl)-2,4-pentadien-1-ol 
• 161431-74-9 Ethyl <(E)-4-(diethoxyphosphonyl)-2-methylbut-2-enoate> 
• 3917-41-7 (2E,4E)-3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienal 
• 165604-91-1 (E,E)-(5-hydroxy-4-methylpenta-1,3-dien-1-yl)boronic acid 
• 98754-72-4 all-trans-13-demethyl-14-methylretinol 
• 53282-28-3 [(2E,4E)-3-methyl-5-(2,6,6-trimethylcyclohex-1-en-1-yl)penta-2,4-dienyl]triphenylphosphonium chloride 
• 94884-86-3 E-β-Formylcrotonaldehyde diethyl acetal 
• 26586-01-6 (E)-4,4-diethoxy-3-methyl-but-2-en-1-ol 
• 62285-98-7 5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide 

Downstream Products

• 128293-05-0 (E,E,E,E)-<2,7-Dimethyl-9-(2,6,6-trimethylcycloxhex-1-enyl)nona-2,4,6,8-tetraenyl>sulfonylbenzene 
• 1027568-72-4 Acetic acid (2E,4E,6E,8E)-2,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraenyl ester 
• 103476-47-7 (2E,4Z,6E,8E)-2,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)-2,4,6,8-nonatetraenal 

Relevant academic research and scientific papers

Synthesis of C11-to-C14 methyl-shifted all-: Trans -retinal analogues and their activities on human aldo-keto reductases

Human aldo-keto reductases (AKRs) are enzymes involved in the reduction, among other substrates, of all-trans-retinal to all-trans-retinol (vitamin A), thus contributing to the control of the levels of retinoids in organisms. Structure-activity relationship studies of a series of C11-to-C14 methyl-shifted (relative to natural C13-methyl) all-trans-retinal analogues as putative substrates of AKRs have been reported. The synthesis of these retinoids was based on the formation of a C10-C11 single bond of the pentaene skeleton starting from a trienyl iodide and the corresponding dienylstannanes and dienylsilanes, using the Stille-Kosugi-Migita and Hiyama-Denmark cross-coupling reactions, respectively. Since these reagents differ by the location and presence of methyl groups at the dienylorganometallic fragment, the study also provided insights into the ability of the different positional isomers to undergo cross-coupling and the sensitivity of these processes to steric hindrance. The resulting C11-to-C14 methyl-shifted all-trans-retinal analogues were found to be active substrates when tested with AKR1B1 and AKR1B10 enzymes, although relevant differences in substrate specificities were noted. For AKR1B1, all analogues exhibited higher catalytic efficiency (kcat/Km) than parent all-trans-retinal. In addition, only all-trans-11-methylretinal, the most hydrophobic derivative, showed a higher value of kcat/Km = 106 000 ± 23 200 mM-1 min-1 for AKR1B10, which is in fact the highest value from all known retinoid substrates of this enzyme. The novel structures, identified as efficient AKR substrates, may serve in the design of selective inhibitors with potential pharmacological interest. This journal is

Effects of the terminal-methyl position and of the length of the conjugated chain on the cis isomers produced by photo-isomerization: Analysis by HPLC and configurational determination by 1H-NMR spectroscopy of isomeric analogues of retinal and β-apo-12′-carotenal

An analogue of retinal (β-apo-12′-carotenal), its terminal-methyl group being shifted from the 13 to 14 (from 13′ to 14′) position, was subjected to direct (iodine-sensitized) photo-isomerization. The configurations of five (seven) isomers of the retinal (β-apo-12β-carotenal) analogue were determined by 1H-NMR spectroscopy to be all-trans, 7-, 9- and 11-mono-cis and 9,11-di-cis (all-trans, 9-, 13- and 13′-mono-cis and 9,13-, 9,13′- and 13,13′-di-cis). Comparative direct photo-isomerization in acetonitrile of the above parent and analogue aldehydes showed that the kinds and the amounts of cis isomer produced in the stationary-state mixtures are drastically affected by the terminal-methyl position and by the length of the conjugated chain. The results are discussed in terms of enhanced polarization upon excitation in the terminal C=O and the neighbouring C=C bonds in the conjugated chain.

Experimental and theoretical analysis of the steric tolerance of the binding site of bacterioopsin with the use of side-chain methyl-shifted retinal analogs

Four positional isomers of trans-retinal (1) differing in the location of the side-chain methyl groups have been prepared by a combination of Wittig and highly stereocontrolled Suzuki coupling reactions. The incubation of 9-demethyl-10-methylretinal (5) w

Retinoids and Related Compounds. Part 14. A Novel Synthesis of Conjugated 4-Alkylidenebutenolides and Their Spectral Characterization

A novel synthesis (the sulfone method) of carotenoidal alkylidenebutenolides is described together with spectral characterization of the latter.

Retinoids and Carotenoids, V.- Synthesis of Modified Retinals

The syntheses of 13-demethyl-13-ethyl-, 13-demethyl-13-propyl-, 13-demethyl-, 13-demethyl-14-methyl-, and 14-methylretinal are described.The UV spectra of some geometric isomers of these compounds are discussed.