18344-42-8

Basic information

• Product Name: all-trans 4-Hydroxyretinal
• Synonyms: 4-Hydroxyretinal;rac all-trans 4-Hydroxy Retinal
• CAS NO: 18344-42-8
• Molecular Formula: C₂₀H₂₈O₂
• Molecular Weight: 300.44
• Product Categories: Various Metabolites and Impurities;Metabolites & Impurities;Retinoids;Intermediates & Fine Chemicals;Pharmaceuticals;Metabolites & Impurities, Pharmaceuticals, Intermediates & Fine Chemicals, Retinoids
• Mol File: 18344-42-8.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 463.9°Cat760mmHg
• Flash Point: 197.4°C
• Appearance: /
• Density: 1.012g/cm³
• Vapor Pressure: 1.47E-10mmHg at 25°C
• Refractive Index: 1.558
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• CAS DataBase Reference: all-trans 4-Hydroxyretinal(CAS DataBase Reference)
• NIST Chemistry Reference: all-trans 4-Hydroxyretinal(18344-42-8)
• EPA Substance Registry System: all-trans 4-Hydroxyretinal(18344-42-8)

Safety Data

• Hazardous Substances Data: 18344-42-8(Hazardous Substances Data)

Usage

Chemical Properties

Redish Semisolid

Uses

A metabolite of Vitamin A.

InChI:InChI=1/C20H28O2/c1-15(7-6-8-16(2)12-14-21)9-10-18-17(3)19(22)11-13-20(18,4)5/h6-10,12,14,19,22H,11,13H2,1-5H3/b8-6+,10-9+,15-7-,16-12-

Upstream product

• 64-19-7 acetic acid 
• 78508-49-3 (2E,4E,6E,8E)-9-(3-Bromo-2,6,6-trimethyl-cyclohex-1-enyl)-3,7-dimethyl-nona-2,4,6,8-tetraenal 
• 14398-34-6 4-(3-hydroxy-2,6,6-trimethylcyclohex-1-enyl)but-3-en-2-one 
• 190059-33-7 (E)-4-(1,3,3-Trimethyl-7-oxa-bicyclo[4.1.0]hept-2-yl)-but-3-en-2-one 
• 127-41-3 alpha-ionone 
• 114034-81-0 4-Oxo-all-trans-retinal-dimethylacetal 
• 116-31-4 all-trans-Retinal 
• 116-31-4 vitamin A aldehyde 
• 76686-06-1 Acetic acid 3-((1E,3E,5E,7E)-3,7-dimethyl-9-oxo-nona-1,3,5,7-tetraenyl)-2,4,4-trimethyl-cyclohex-2-enyl ester 
• 76686-06-1 all-trans 4-acetoxyretinal 
• 123080-87-5 (+/-)-4-Hydroxy-all-trans-retinal-dimethylacetal 
• 15401-34-0 3-hydroxy-β-ionone 
• 37677-81-9 4-(1,3,3-trimethyl-7-oxabicyclo[4.1.0]hept-2-yl)-3-buten-2-one 
• 1209-68-3 3-methyl-5-(2,6,6-trimethylcyclohex-1-enyl)penta-2, 4-dienal 

Downstream Products

• 76686-02-7 2-(4'-hydroxyretinylidene)-dimedone 
• 71423-69-3 4-keto-13-cis-retinal 
• 33532-44-4 4-keto-all-trans-retinal 
• 129467-12-5 3-formyl-4-ketoretinyl tert-butyldimethylsilyl ether 
• 129467-11-4 4-ketoretinyl tert-butyldimethylsilyl ether 
• 129467-08-9 6-diazo-3-[(1E,3E,5E,7Z)-8-formyl-3,7-dimethylnona-1,3,5,7-tetraenyl]-2,4,4-trimethylcyclohex-2-en-1-one 
• 129467-13-6 3-formyl-4-ketoretinol 
• 62702-55-0 4-ketoretinol 
• 76686-03-8 2-(4'-oxoretinylidene)-dimedone 
• 160397-98-8 (-)-(S)-13-cis-4-hydroxyretinal 
• 140387-20-8 (-)-(4R)-11Z-4-hydroxyretinal 
• 160398-00-5 (+)-(R)-13-cis-4-hydroxyretinal 
• 33532-44-4 4-ketoretinal 

Relevant articles and documents

One step and convenient preparations of 4-hydroxyretinal and 4- oxoretinal

Treatment of all-trans-retinal with one and two equivalents of NBS in a mixture of CH3CN-CH2Cl2-H2O provide 4-hydroxyretinal and 4-oxoretinal, respectively, in good yields.

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.

Iron(III)Porphinate/H2O2-Mediated Conversion of All-(E)-Retinol

The reaction of hydrogen peroxide with all-(E)-retinol (1) catalyzed by (meso-tetraphenylporphinato)iron(III) led to the formation of 4-hydroxyretinol (2), 4-oxoretinol (3), 5,8-epoxyretinol (4), 5,6-epoxyretinol (5), 3-dehydroretinol (6), all-(E)- and 12-(Z)-retroretinol (7/7a) as well as all-(E)- and 12-(Z)-anhydroretinol (8/8a) as major non-volatile products.The conversion products were characterized by comparison of their chromatographic (HPLC) and spectroscopic data (UV; MS; 1H and 13C NMR) with those of synthesized reference compounds.The observed product formation supports the hypothesis of a C4 centered radical as the key intermediate of all-(E)-retinol conversion. - Keywords: 5,6- and 5,8-Epoxyretinol, 4-Hydroxyretinol, 4-Oxoretinol, Retinol Conversion