67737-36-4

Basic information

• Product Name: 9-cis,11-cis,13-cis-retinal
• Synonyms: 9-cis,11-cis,13-cis-retinal
• CAS NO: 67737-36-4
• Molecular Weight: 284.442
• Mol File: 67737-36-4.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: 9-cis,11-cis,13-cis-retinal(CAS DataBase Reference)
• NIST Chemistry Reference: 9-cis,11-cis,13-cis-retinal(67737-36-4)
• EPA Substance Registry System: 9-cis,11-cis,13-cis-retinal(67737-36-4)

Safety Data

• Hazardous Substances Data: 67737-36-4(Hazardous Substances Data)

Upstream product

• 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 
• 116-31-4 all-trans-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 
• 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 
• 119718-30-8 7-cis,9-cis,11-cis-retinonitrile 
• 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 
• 157886-41-4 (E)-4-iodo-3-methyl-3-buten-1-al, diethylacetal 
• 1209-68-3 3-methyl-5-(2,6,6-trimethylcyclohex-1-enyl)penta-2, 4-dienal 
• 134962-99-5 4-Methyl-6-[(1E,3E)-2-methyl-4-(2,6,6-trimethyl-cyclohex-1-enyl)-buta-1,3-dienyl]-5,6-dihydro-2H-pyran-2-ol 
• 84303-93-5 Z-4-bromo-3-methyl-3-buten-1-yl-tert-butyldimethylsilyl ether 

Downstream Products

• 23790-80-9 9-cis,13-cis-retinal 
• 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 
• 71423-68-2 4-hydroxy-13-cis-retinal 
• 18344-42-8 4-hydroxy-all-trans-retinal 
• 739-13-9 5,6-epoxy-5,6-dihydroretinal 
• 71423-69-3 4-keto-13-cis-retinal 
• 33532-44-4 4-keto-all-trans-retinal 

Relevant articles and documents

Vinyltin acetals in terpenic and nor-terpenic synthesis

Vinyltin acetals obtained by stannylmetallation of homopropargyl acetals with Bu3SnMgMe/CuCN (E configuration) or by titanation of the corresponding alkyltin acetals (Z configuration) have been proved to be efficient storable precursors for the stereoselective synthesis of terpenoids, under mild experimental conditions.Due to the presence of a nucleophilic centre (Csp2-Sn bond) and of a protected electrophilic centre, they are also useful intermediates for an iterative synthesis of retinal and nor-retinoids. - Keywords: vinyltin; acetal; vinyllithium; monoterpenoid; retinal; nor-retinoid

Photoisomerization of Hindered Poly-cis Isomers of Retinal. Regioselectivity And One -Photon-Multiple-Bond Isomerization.

Direct irradiation of five dicis (7,9, 7,11, 7,13, 9,11 and 9,13) and one tricis (7,9,11) isomers of retinal led to regioselective isomerization at the 13,14 bond as well as multiple-bond isomerization.

Thermal Sigmatropic Rearrangements of Vinylallenes Leading to 11-cis-Retinoids and the Novel Properties of 9-cis,11-cis,13-cis-Retinal and 11-cis,13-cis-Retinal

The thermally induced sigmatropic hydrogen shift of vinylallene 5 provided a route to highly hindered 11-cis-retinoids.The coupling ot the hetero cuprate 14 with the propargyl benzoate 13b gave the vinylallene 5, which upon heating (69 deg C, 2 h) gave three geometrically isomeric retinoids: 11-sis (8), 11-cis,13-cis (9), and 9-cis,11-cis,13-cis (11).The fourth possible geometric isomer, 9-cis,11-cis (10), was unstable to the conditions of thermolysis and underwent further electrocyclizations to the tricyclic compound 22.The thermal rearramgement of 9,10-allene 5, though highly specific for the formation of 11-cis-retinoids, exhibits no selectivity in the formation of Δ9 and Δ13 double bonds.The highly hindered 11-cis,13-cis- and 9-cis,11-cis,13-cis-retinals, 9b and 11b, exhibit extraordinary electronic absorption spectra in that they exhibit their main maxima (302 nm) actually to the blue of the corresponding alcohols.The retinals 9b and 11b were thermally unstable and underwent clean isomerization to 13-cis-retinal and 9-cis,13-cis-retinal, respectively.