25576-25-4

Usage

Uses

1. Used as an intermediate in the preparation of Retinoic Acid derivatives:
1,3,3-TriMethyl-2-[(1E,3E)-3-Methyl-1,3-hexadien-5-ynyl]-cyclohexane is utilized as a crucial intermediate in the synthesis of Retinoic Acid derivatives. Retinoic Acid, a metabolite of Vitamin A, plays a vital role in various biological processes, including cell growth, differentiation, and embryonic development. The compound's unique structure allows it to serve as a key building block in the development of these important pharmaceutical compounds.
Different applications in different industries:
Used in Pharmaceutical Industry:
1,3,3-TriMethyl-2-[(1E,3E)-3-Methyl-1,3-hexadien-5-ynyl]-cyclohexane is used as a synthetic intermediate for the production of various pharmaceutical compounds. Its unique structure and reactivity make it a valuable asset in the development of new drugs and therapeutic agents.
Used in Chemical Industry:
In the chemical industry, 1,3,3-TriMethyl-2-[(1E,3E)-3-Methyl-1,3-hexadien-5-ynyl]-cyclohexane can be employed as a starting material for the synthesis of various specialty chemicals, including fragrances, dyes, and other organic compounds. Its versatility and unique structural features make it an attractive candidate for further exploration and development in this field.
Used in Research and Development:
1,3,3-TriMethyl-2-[(1E,3E)-3-Methyl-1,3-hexadien-5-ynyl]-cyclohexane is also used in research and development settings, where its unique chemical properties and reactivity can be explored for potential applications in various scientific and technological fields. Researchers may investigate its potential use in the development of new materials, catalysts, or other innovative applications.

Upstream product

• 3917-41-7 (2E,4E)-3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienal 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 884845-78-7 N-benzyl-N-methoxy-3-(2,6,6-trimethyl-cyclohex-1-enyl)-acrylamide 
• 79-77-6 (E)-β-ionone 
• 3917-39-3 (2E,4E)-3-methyl-5-(2,6,6-trimethyl-1-cyclohexenyl)-2,4-pentadien-1-ol 
• 37384-77-3 ethyl β-ionylidene acetate 
• 74352-11-7 6-(2-methyl-6,6-dimethylcyclohex-1-en-1-yl)-3-methylhex-1-ene-5-yne-3-ol 
• 17974-55-9 (2E,4E)-ethyl 3-methyl-5-(2,6,6-trimethylcyclohex-1-enyl)penta-2,4-dienoate 
• 22029-76-1 beta-ionol 
• 303779-99-9 (E)-2-(2,6,6-trimethylcyclohexen-1-yl)-ethenyl (trifluoromethyl)sulfonate 
• 74352-12-8 9-(2-propynyl)-β-ionyl acetate 
• 917-54-4 methyllithium 
• 79985-69-6 (2E,4E,6E)-2-Fluoro-5-methyl-7-(2,6,6-trimethyl-cyclohex-1-enyl)-hepta-2,4,6-trienoic acid 
• 624-67-9 Propargylic aldehyde 

Downstream Products

• 2130-29-2 1,18-Bis-<2,2,6-trimethyl-cyclohexen-(6)-yl>-7,12-dihydroxy-3,7,12,16-tetramethyl-octadeca-pentaen-(1,3,9,15,17)-diin-(5,13) 
• 59699-82-0 ethyl 13-cis-retinoate 
• 3899-20-5 ethyl (all-E)-retinoate 
• 353744-04-4 ethyl (2E,4E,6E,8E)-3-butyl-7-methyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoate 
• 353744-01-1 ethyl (2E,4E,6E,8E)-3-ethyl-7-methyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoate 
• 353744-02-2 ethyl (2E,4E,6E,8E)-7-methyl-3-propyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoate 
• 353744-05-5 ethyl (2E,4E,6E,8E)-7-methyl-3-(2-phenyl)ethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoate 
• 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 
• 885050-34-0 [9,10-13C₂]-11Z-retinol 
• 29443-88-7 (2E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,6,8-trien-4-yn-1-ol 
• 68-26-8 vitamine A 
• 302-79-4 all-trans-retinoic-acid 
• 22737-96-8 11-cis-retinol 
• 68-26-8 RETINOL 

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.

Carboxylate-directed tandem functionalisations of α,β- dihaloalkenoic acids with 1-alkynes: A straightforward access to (Z)-configured, α,β-substituted γ-alkylidenebutenolides

An easy and mild copper(I)-catalysed lactonisation of readily available (E)-2,3-dihalopropenoic acid derivatives regio- and stereoselectively leads to rarely described (Z)-3-halo-5-ylidene-5H-furan-2-ones. These compounds are subsequently able to undergo classical Pd-catalysed cross-coupling reactions, providing 3-substituted and 3,4-disubstituted 5-ylidene-5H-furan-2-ones (see scheme).

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

Preparation and biological activity of 13-substituted retinoic acids

13-Demethyl or 13-substituted all-E- and 9Z-retinoic acids were synthesized using a palladium-catalyzed coupling reaction of enol triflates and tributylstannylolefins. Their biological activities were then measured. The 13-ethyl analogs exhibited approximately one-half of the antiproliferative and differentiation-inducing activity of ATRA in HL-60 cells. In contrast, in the 9Z-derivatives, all analogs, except for the 13-butyl derivatives, showed apoptosis-inducing activity.

Stereocontrolled synthesis of 13-substituted retinoic acids by palladium-catalyzed coupling reaction of alkenyl stannane with vinyl triflate

A novel method for the stereoselective synthesis of all-E-, 13Z- and 9Z- retionic acid esters was developed by palladium-catalyzed cross coupling reactions of tetraenyl stannanes with E- or Z-vinyl triflates in good yields. Applying this methodology, 13-substituted all-E- and 9Z- retinoic acids were prepared in satisfactory yields.

10-Mono-, 11-mono-, 12-mono and 11,12-dideuteroretinal

The 11-mono and 12-mono- and 11,12-dideuteroretinal (in the all-trans, 9-cis, 11-cis and 13-cis form) with > 98percent chemical purity and > 95percent mono- and dideuterium incorporation were prepared using the same scheme for all three compounds.The all-