23790-80-9

Basic information

• Product Name: 9-cis,13-cis-retinal
• Synonyms: 9-cis,13-cis-retinal
• CAS NO: 23790-80-9
• Molecular Weight: 284.442
• Mol File: 23790-80-9.mol
• Article Data: 15

Chemical Properties

• CAS DataBase Reference: 9-cis,13-cis-retinal(CAS DataBase Reference)
• NIST Chemistry Reference: 9-cis,13-cis-retinal(23790-80-9)
• EPA Substance Registry System: 9-cis,13-cis-retinal(23790-80-9)

Safety Data

• Hazardous Substances Data: 23790-80-9(Hazardous Substances Data)

Upstream product

• 29444-25-5 (9Z,13Z)-retinol 
• 74916-02-2 12,14-retro-retinol 
• 119718-30-8 7-cis,9-cis,11-cis-retinonitrile 
• 116-31-4 all-trans-Retinal 
• 564-87-4 (11Z)-retinal 
• 67737-36-4 9-cis,11-cis,13-cis-retinal 
• 135322-87-1 Bis-(2,2,2-trifluoroethyl)-2-methyl-3-cyano-2-propenyl phosphonate 
• 56013-13-9 7-cis,9-cis-β-ionylideneacetaldehyde 
• 3899-20-5 (2E,4Z,6Z,8Z)-3,7-Dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraenoic acid ethyl ester 
• 68-26-8 (2Z,4Z,6Z,8Z)-3,7-Dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraen-1-ol 
• 58274-64-9 (E)-trimethyl((3-methylbuta-1,3-dien-1-yl)oxy)silane 
• 5560-99-6 (2X,4E)-3-methyl-5-(2,6,6-trimethyl-cyclohex-1-enyl)-penta-2,4-dienal 
• 211235-94-8 (E)-5,5-diethoxy-3-methyl-1-(2,6,6-trimethylcyclohex-1-enyl)pent-2-en-1-ol 
• 162889-29-4 C₉H₁₇LiO₂ 

Downstream Products

• 514-85-2 9-cis vitamin A aldehyde 
• 472-86-6 13-cis-vitamin A aldehyde 
• 116-31-4 all-trans-Retinal 
• 56085-55-3 7-cis,9-cis,13-cis-retinal 
• 56085-53-1 7,9,13-tricis-retinal 
• 67737-37-5 All-cis-Retinal 
• 71423-69-3 4-keto-13-cis-retinal 
• 33532-44-4 4-keto-all-trans-retinal 
• 71423-68-2 4-hydroxy-13-cis-retinal 
• 18344-42-8 4-hydroxy-all-trans-retinal 
• 739-13-9 5,6-epoxy-5,6-dihydroretinal 
• 302-79-4 9-cis-retinoic acid 
• 302-79-4 9,13-di-cis-retinoic acid 

Relevant articles and documents

Human cellular retinaldehyde-binding protein has secondary thermal 9-cis-retinal isomerase activity

Cellular retinaldehyde-binding protein (CRALBP) chaperones 11-cis-retinal to convert opsin receptor molecules into photosensitive retinoid pigments of the eye. We report a thermal secondary isomerase activity of CRALBP when bound to 9-cis-retinal. UV/vis and 1H NMR spectroscopy were used to characterize the product as 9,13-dicis-retinal. The X-ray structure of the CRALBP mutant R234W:9-cis-retinal complex at 1.9 A resolution revealed a niche in the binding pocket for 9-cis-aldehyde different from that reported for 11-cis-retinal. Combined computational, kinetic, and structural data lead us to propose an isomerization mechanism catalyzed by a network of buried waters. Our findings highlight a specific role of water molecules in both CRALBP-assisted specificity toward 9-cis-retinal and its thermal isomerase activity yielding 9,13-dicis-retinal. Kinetic data from two point mutants of CRALBP support an essential role of Glu202 as the initial proton donor in this isomerization reaction.

Stereospecific thermal rearrangement of the four labile isomers of retinal. Activation parameters and FT-IR data

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Palladium-catalysed vinylation of tertiary allylic alcohols: A new protocol for the synthesis of isoprenoid aldehydes.

Heck vinylation of tertiary allylic alcohols with iodo-acetal Ic, followed by an acid catalysed acetal hydrolysis-dehydration reaction, furnished isoprenoid aldehydes regioselectively in high yields.