29443-88-7

Usage

Chemical Properties

Orange Oil

Uses

11-cis Retinal intermediate.

Upstream product

• 6153-06-6 (E)-3-methylpent-2-en-4-yn-1-ol 
• 14398-40-4 (E)-2-methyl-4-(2,6,6-trimethyl-1-cyclohexenyl)-2-butenal 
• 79-77-6 (E)-β-ionone 
• 3917-41-7 (2E,4E)-3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienal 
• 17974-55-9 (2E,4E)-ethyl 3-methyl-5-(2,6,6-trimethylcyclohex-1-enyl)penta-2,4-dienoate 
• 103633-89-2 3-(β-ionilidene)-1-propyne 
• 37384-77-3 ethyl β-ionylidene acetate 
• 25576-25-4 (3E,5E)-4-methyl-6-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3,5-hexadien-1-yne 
• 3917-39-3 (2E,4E)-3-methyl-5-(2,6,6-trimethyl-1-cyclohexenyl)-2,4-pentadien-1-ol 
• 884845-78-7 N-benzyl-N-methoxy-3-(2,6,6-trimethyl-cyclohex-1-enyl)-acrylamide 
• 210700-51-9 ((2E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)nona-2,6,8-trien-4-ynyloxy)(tert-butyl)dimethylsilane 
• 50895-69-7 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)nona-2E,7E-dien-4-yne-1,6-diol 
• 3230-75-9 (+/-)-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2t,7ξ-dien-4-yne-1,6-diol 

Downstream Products

• 22737-96-8 11-cis-retinol 
• 68-26-8 RETINOL 
• 1430344-84-5 (11E)-11-benzyldimethylsilyl-12-deuteroretinol 
• 1430344-82-3 11,12-dehydroretinyl benzyldimethylsilyl ether 
• 1430344-85-6 (11E)-11-benzyldimethylsilylretinol 
• 1430344-81-2 (11E)-12-benzyldimethylsilylretinol 
• 1430344-80-1 (11E)-11-triethoxysilylretinol 
• 74410-14-3 11-cis-11,12-dideuteroretinal 
• 564-87-4 (11Z)-retinal 
• 1430344-87-8 11-cis-11-deuteroretinol 
• 1430344-86-7 11-cis-11-deuteroretinol 
• 31414-91-2 [(2E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,6,8-trien-4-ynyl]-triphenyl-phosphonium; bromide 
• 201658-43-7 (11Z,11'Z)-β,β-carotene 
• 4517-40-2 11,12,11',12'-tetradehydro-β,β-carotene 

Relevant academic research and scientific papers

Syntheses of 13C2-labelled 11Z-retinals

To enable solid-state NMR investigations of the rhodopsin chromophore and its photointermediates, a series of 11Z-retinal isotopomers have been synthesised containing pairs of adjacent 13C labels at C9/C10, C10/C11 or C11/C12, respectively. The C9 labelled carbon atom was introduced through the Heck reaction of a 13C-labelled Weinreb acrylamide derivative, and the label at the C12 position derived from a 13C-containing ethoxy Bestmann-Ohira reagent. The 13C labels at C10 and C11 were introduced through the reaction of β-ionone with labelled triethyl phosphonoacetate.

Accurate measurements of 13C-13C J-couplings in the rhodopsin chromophore by double-quantum solid-state NMR spectroscopy

A new double-quantum solid-state NMR pulse sequence is presented and used to measure one-bond 13C-13C J-couplings in a set of 13C2-labeled rhodopsin isotopomers. The measured J-couplings reveal a perturbation of the electronic structure at the terminus of the conjugated chain but show no evidence for protein-induced electronic perturbation near the C11-C12 isomerization site. This work establishes NMR methodology for measuring accurate 1JCC values in noncrystalline macromolecules and shows that the measured J-couplings may reveal local electronic perturbations of mechanistic significance. Copyright

Efficient synthesis of 11-cis-retinoids

The light sensitivity and unstable nature of 11-cis-retinoids makes them ideal visual chromophores in nature. The synthesis of 11-cis-retinal analogues is of paramount importance in bioorganic studies of rhodopsin, the photoreceptor of the visual transduction pathway, but the instability of 11- cis-retinoids complicates their synthesis and there is no general synthetic route. Common strategies to the cis geometry have failed in the case of 11- cis-retinoids, and most often low yields and complex isomeric mixtures are obtained. Herein we report an efficient, general, and mild preparation of 11- cis-retinoids by semi-hydrogenation of 11-yne-retinoid precursors with Cu/Ag- activated zinc dust.