19907-28-9

Basic information

• Product Name: 5,6-dihydroretinal
• Synonyms: 5,6-dihydroretinal;Retinal, 5,6-dihydro-;3,7-Dimethyl-9-(2,2,6-trimethyl-cyclohexyl)-nona-2,4,6,8-tetraenal
• CAS NO: 19907-28-9
• Molecular Formula: C₂₀H₃₀O
• Molecular Weight: 286.45
• Mol File: 19907-28-9.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 405.2°Cat760mmHg
• Flash Point: 186.9°C
• Appearance: /
• Density: 0.922g/cm³
• Vapor Pressure: 8.91E-07mmHg at 25°C
• Refractive Index: 1.52
• CAS DataBase Reference: 5,6-dihydroretinal(CAS DataBase Reference)
• NIST Chemistry Reference: 5,6-dihydroretinal(19907-28-9)
• EPA Substance Registry System: 5,6-dihydroretinal(19907-28-9)

Safety Data

• Hazardous Substances Data: 19907-28-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C20H30O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,15,18-19H,7,10,14H2,1-5H3/b9-6+,12-11+,16-8+,17-13+

Upstream product

• 62924-16-7 all-trans-5-(2,2,6-Trimethyl-cyclohexyl)-3-methyl-pentadien-(2,4)-al 
• 4350-74-7 (1R,6S)-2,2,6-trimethylcyclohexyl carbaldehyde 
• 57576-59-7 3,7-dimethyl-octa-1,6-dien-1-yl acetate 
• 106-23-0 3,7-dimethyl-oct-6-enal 
• 82648-70-2 diethyl (3-cyano-2-methyl-2-trans-propenyl)phosphonate 

Relevant articles and documents

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.