58526-71-9

Upstream product

• 79-77-6 4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-buten-2-one 
• 3917-41-7 (2E,4E)-3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienal 
• 2537-48-6 diethyl 1-cyanomethylphosphonate 
• 105175-91-5 3-methyl-5-(2’,6’,6’-trimethylcyclohex-1’-en-1’-yl)-penta-2,4-dienenitrile 
• 62924-18-9 β-ionylidene-acetonitrile 
• 72214-33-6 3-(2,6,6-Trimethylcyclohex-1-enyl)prop-2-enenitrile 
• 472-80-0 beta-Ionol 
• 53018-97-6 3-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-propenal 
• 19834-52-7 3-Methyl-1-(2,6,6-trimethyl-cyclohexen-⁽¹⁾-yl)-pentadien-(1,3)-saeure-⁽⁵⁾-nitril 
• 1209-68-3 3-methyl-5-(2,6,6-trimethylcyclohex-1-enyl)penta-2, 4-dienal 
• 372-09-8 cyanoacetic acid 
• 6488-41-1 Cyan-<β-ionyliden-aethyliden>-essigsaeure 
• 6980-79-6 (2E,4E,6E)-5-methyl-7-(2’,6’,6’-trimethylcyclohex-1’-en-1’-yl)-hepta-2,4,6-trienenal 

Downstream Products

• 129165-44-2 (2E,4E,6E,8E)-7-methyl-9-(2’,6’,6’-trimethylcyclohex-1’-en-1’-yl)-nona-2,4,6,8-tetraenenitrile 
• 24336-20-7 7-methyl-9-(2,6,6-trimethylcyclohex-1-enyl)nona-2,4,6,8-tetraenal 
• 6980-79-6 (2E,4E,6E)-5-methyl-7-(2’,6’,6’-trimethylcyclohex-1’-en-1’-yl)-hepta-2,4,6-trienenal 
• 20638-88-4 retinonitrile 
• 99302-31-5 retinal 
• 99302-30-4 retinal 
• 1220-77-5 6-methyl-8-(2,6,6-trimethyl-1-cyclohexenyl)-3,5,7-octatriene-2-one 
• 116-31-4 all-trans-Retinal 
• 6980-79-6 (2E,4E,6E)-5-Methyl-7-(2,6,6-trimethyl-cyclohex-1-enyl)-hepta-2,4,6-trienal 
• 4435-26-1 all-trans-β-Jonyliden-crotonsaeure 

Relevant academic research and scientific papers

COMPOUNDS AND METHODS OF TREATING OCULAR DISORDERS

A method of treating an ocular disorder in a subject associated with increased all-trans-retinal in an ocular tissue includes administering to the subject a therapeutically effective amount of a primary amine compound of formula (I); and pharmaceutically acceptable salts thereof.

Synthetic control of retinal photochemistry and photophysics in solution

Understanding how molecular structure and environment control energy flow in molecules is a requirement for the efficient design of tailor-made photochemistry. Here, we investigate the tunability of the photochemical and photophysical properties of the retinal-protonated Schiff base chromophore in solution. Replacing the n-butylamine Schiff base normally chosen to mimic the saturated linkage found in nature by aromatic amines results in the reproduction of the opsin shift and complete suppression of all isomerization channels. Modification of retinal by directed addition or removal of backbone substituents tunes the overall photoisomerization yield from 0 to 0.55 and the excited state lifetime from 0.4 to 7 ps and activates previously inaccessible reaction channels to form 7-cis and 13-cis products. We observed a clear correlation between the presence of polarizable backbone substituents and photochemical reactivity. Structural changes that increase reaction speed were found to decrease quantum yields, and vice versa, so that excited state lifetime and efficiency are inversely correlated in contrast to the trends observed when comparing retinal photochemistry in protein and solution environments. Our results suggest a simple model where backbone modifications and Schiff base substituents control barrier heights on the excited-state potential energy surface and therefore determine speed, product distribution, and overall yield of the photochemical process.

Synthesis of 8-, 9-, 12-, and 13-mono-13C-retinal

The 8-, 9-, 12-, and 13-mono-13C-retinals were synthesized with >98percent chemical purity and 93percent 13C incorporation from 13C-labelled acetonitrile.Their 13C-13C and 13C-1H nmr coupling constants were determined.