76686-22-1

Upstream product

• 72152-84-2 2,6,6-trimethylcyclohexa-1,3-dienecarbonitrile 
• 76686-21-0 (3S)-3-Hydroxy-β-cyclogeraniol 
• 121401-81-8 (S)-4-(1-Methoxy-1-methyl-ethoxymethyl)-3,5,5-trimethyl-cyclohex-3-enol 
• 76686-19-6 1-(1-Methoxy-1-methyl-ethoxymethyl)-2,6,6-trimethyl-cyclohexa-1,3-diene 
• 4436-51-5 1-hydroxymethyl-2,6,6-trimethylcyclohexa-1,3-diene 
• 5146-66-7 geranonitrile 
• 5585-39-7 (E)-3,7-dimethylocta-2,6-dienenitrile 
• 110-93-0 6-Methyl-hept-5-en-2-on 
• 1373498-20-4 C₁₁H₁₈O 
• 1373498-18-0 C₁₁H₁₈O 
• 264279-20-1 2,3-epoxy-2,6,6-trimethyl-1-cyclohexanecarbonitrile 
• 145106-79-2 3-hydroxy-2,6,6-trimethylcyclohex-1-enecarbonitrile 
• 57524-13-7 2,6,6-trimethyl-2-cyclohexenecarbonitrile 
• 535950-00-6 3,4-epoxy-2,6,6-trimethylcyclohex-1-enecarbonitrile 

Downstream Products

• 116-26-7 safranal 
• 6890-91-1 (3RS,all-E)-hydroxyretinal 
• 121429-38-7 (E)-3-[(S)-4-(tert-Butyl-dimethyl-silanyloxy)-2,6,6-trimethyl-cyclohex-1-enyl]-propenal 
• 121401-85-2 (E)-3-[(S)-4-(tert-Butyl-dimethyl-silanyloxy)-2,6,6-trimethyl-cyclohex-1-enyl]-acrylonitrile 
• 121468-86-8 (E)-4-[(S)-4-(tert-Butyl-dimethyl-silanyloxy)-2,6,6-trimethyl-cyclohex-1-enyl]-but-3-en-2-one 
• 121401-86-3 (E)-4-[(S)-4-(tert-Butyl-dimethyl-silanyloxy)-2,6,6-trimethyl-cyclohex-1-enyl]-but-3-en-2-ol 
• 121468-87-9 (2Z,4E)-5-[(S)-4-(tert-Butyl-dimethyl-silanyloxy)-2,6,6-trimethyl-cyclohex-1-enyl]-3-methyl-penta-2,4-dienal 
• 121521-19-5 3S-hydroxy-9-cis-retinal 
• 121521-22-0 (2E,4E,6Z,8E)-9-((S)-4-Hydroxy-2,6,6-trimethyl-cyclohex-1-enyl)-3,7-dimethyl-nona-2,4,6,8-tetraenenitrile 
• 121401-89-6 (2E,4E,6Z,8E)-9-[(S)-4-(tert-Butyl-dimethyl-silanyloxy)-2,6,6-trimethyl-cyclohex-1-enyl]-3,7-dimethyl-nona-2,4,6,8-tetraenenitrile 
• 144-68-3 lutein 

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.

Expansion of first-in-class drug candidates that sequester toxic all-trans-retinal and prevent light-induced retinal degeneration

All-trans-retinal, a retinoid metabolite naturally produced upon photoreceptor light activation, is cytotoxic when present at elevated levels in the retina. To lower its toxicity, two experimentally validated methods have been developed involving inhibition of the retinoid cycle and sequestration of excess of all-trans-retinal by drugs containing a primary amine group. We identified the first-in-class drug candidates that transiently sequester this metabolite or slow down its production by inhibiting regeneration of the visual chromophore, 11-cis-retinal. Two enzymes are critical for retinoid recycling in the eye. Lecithin:retinol acyltransferase (LRAT) is the enzyme that traps vitamin A (all-trans-retinol) from the circulation and photoreceptor cells to produce the esterified substrate for retinoid isomerase (RPE65), which converts all-trans-retinyl ester into 11-cis-retinol. Here we investigated retinylamine and its derivatives to assess their inhibitor/substrate specificities for RPE65 and LRAT, mechanisms of action, potency, retention in the eye, and protection against acute light-induced retinal degeneration in mice. We correlated levels of visual cycle inhibition with retinal protective effects and outlined chemical boundaries for LRAT substrates and RPE65 inhibitors to obtain critical insights into therapeutic properties needed for retinal preservation.

Total synthesis of (±)-3-hydroxy-β-ionone through a ring-closing enyne metathesis

The total synthesis of (±)-3-hydroxy - ionone, a bisnor-sesquiterpene having allelopathic activity, has been accomplished employing an enyne metathesis for the construction of the C1-C8 segment and two-carbon elongation via a nitrile oxide-alkene [3+2] cycloaddition as the key steps. Georg Thieme Verlag Stuttgart · New York.

Synthetic scheme for the preparation of 13C-labeled 3,4-didehydro-retinal, 3-hydroxyretinal, and 4-hydroxyretinal up to uniform 13C-enrichment

A modular synthetic scheme has been developed for the synthesis of 13C-labeled naturally occurring visual pigment chromophores; 3,4-didehydroretinal, 3-hydroxyretinal, and 4-hydroxyretinal. These compounds can now be made with > 99% 13C enrichment at any position or combination of positions. We used the common C10+C5+C5 scheme for the synthesis of retinals, and by making variations in the C10 part we can now prepare the desired retinal derivatives with selective or uniform 13C enrichment. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.

SYNTHESIS OF OPTICALLY ACTIVE 3-DIAZOACETYLRETINALS WITH TRIISOPROPYLPHENYLSULFONYLHYDRAZONE

An improved synthesis of photoaffinity labeled, optically active retinal derivatives is presented.A stable, easy to handle, glyoxalic acid 2,4,6-triisopropylphenylsulfonylhydrazone (TIPPS) reacts with 3-hydroxyretinal to give the diazoacetylretinal analog in satisfactory yield.

154. Synthese von optisch aktiven, natuerlichen Carotinoiden und strukturell verwandten Naturprodukten. V. Synthese von (3R,3'R)-, (3S,3'S)- und (3R,3'S; meso)-Zeaxanthin durch asymmetrische Hydroborierung. Ein neuer Zugang zu optisch aktiven Carotinoidba

The synthesis of (3R,3'R)-, (3S,3'S)- and (3R,3'S; meso)-zeaxanthin (1), (19) and (21) is reported utilizing asymmetric hydroboration as the key reaction.Thus, safranol isopropenylmethylether (4) is hydroborated with (+)- and (-)-(IPC)2BH to give the opti