17974-55-9

Usage

Structure

An ethyl ester derivative of 2,4-pentadienoic acid with a 3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl) group

Usage

Perfumes and fragrance products due to its pleasant aroma

Potential applications

Flavoring industry

Reactivity

Utilized in the synthesis of other organic compounds

Chemical properties

Versatile chemical properties due to its structure and reactivity

Upstream product

• 79-77-6 (E)-β-ionone 
• 927-80-0 1-ethoxyacetylene 
• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 
• 69445-88-1 (triethyl-λ⁵-phosphanylidene)-acetic acid ethyl ester 
• 105-36-2 ethyl bromoacetate 
• 141208-06-2 (2E)-N-methoxy-N-methyl-3-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-propenamide 
• 311-46-6 ethyl 2-(dimethoxyphosphoryl)acetate 
• 174836-75-0 (E)-5-(2,6,6-Trimethyl-cyclohex-1-enyl)-pent-4-en-2-ynoic acid ethyl ester 

Downstream Products

• 14398-42-6 (2E,4E)-3-methyl-5-(2,6,6-trimethylcyclohex-1-enyl)penta-2,4-dienoic acid 
• 103476-47-7 (2E,4Z,6E,8E)-2,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)-2,4,6,8-nonatetraenal 
• 53121-26-9 all-trans-13-demethyl-14-methylretinal 
• 128293-05-0 (E,E,E,E)-<2,7-Dimethyl-9-(2,6,6-trimethylcycloxhex-1-enyl)nona-2,4,6,8-tetraenyl>sulfonylbenzene 
• 62285-98-7 5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide 
• 98754-72-4 all-trans-13-demethyl-14-methylretinol 
• 1027568-72-4 Acetic acid (2E,4E,6E,8E)-2,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraenyl ester 
• 43059-50-3 4-methyl-6-[(1E,3E)-2-methyl-4-(2,6,6-trimethylcyclohex-1-en-1-yl)buta-1,3-dien-1-yl]-5,6-dihydro-2H-pyran-2-one 
• 4759-48-2 13-cis-retinoic acid 
• 115797-14-3 13,14-dihydro-all-trans retinol 
• 172302-35-1 13,14-dihydroretinal 
• 98299-59-3 all-trans-13,14-dihydroretinoic acid 
• 879295-61-1 11-cis-DROL 

Relevant academic research and scientific papers

An efficient commercial process for the preparation of isotretinoin

We describe an efficient process for the preparation of isotretinoin (13-cis isomer of vitamin A acid) in a single step starting from β-ionylidene acetaldehyde (5). The process conditions are convenient to operate on a commercial scale and afford isotretinoin of excellent quality; levels of related isomeric impurities such as tretinoin (all trans retinoic acid) and 9,13-di-cis-retinoic acid are extremely low. Thus, condensation of dienolate of methyl 3,3-dimethylacrylate with β-ionylidene acetaldehyde (5) followed by aqueous acidic workup afforded isotretinoin in >95% purity. The condensation reaction proceeds via in situ formation of lactone (8); furthermore, the reaction conditions have been optimized to exploit in situ generated methoxide anion for lactone ring opening to afford the desired product. Distinct advantages of this process are that it does not require isolation of intermediate lactone and utilizes in situ generated methoxide for lactone ring opening, thus obviating the need for an additional step and base. We also describe an optimized process for the preparation of β-ionylidene acetaldehyde (5), a key intermediate for isotretinoin.

Photocatalytic e → Z Isomerization of β-Ionyl Derivatives

An operationally simple E → Z isomerization of activated dienes, based on the β-ionyl motif intrinsic to retinal, is reported using inexpensive (-)-riboflavin (vitamin B2) under irradiation at 402 nm. Selective energy transfer from photoexcited (-)-riboflavin to the starting E-isomer enables geometrical isomerization. Since the analogous process with the Z-isomer is inefficient, microscopic reversibility is circumvented, thereby enabling a directional isomerization to generate the contra-thermodynamic product (up to 99% yield, up to 99:1 Z/E). Prudent choice of photocatalyst enables chemoselective isomerization to be achieved in both inter- and intramolecular systems. The principles established from this study, together with a molecular editing approach, have facilitated the development of a regioselective isomerization of a truncated triene based on the retinal scaffold.

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.

Effect of conjugates of all-trans-retinoic acid and shorter polyene chain analogues with amino acids on prostate cancer cell growth

In the present work, a series of conjugates of amino acids with all-trans-retinoic acid (ATRA) and shorter polyene chain analogues were rationally designed, synthesized by coupling the succinimidyl active esters of the acidic retinoids with appropriately

All-Trans-Retinol: All-Trans-13,14-Dihydroretinol Saturase and Methods of Its Use

Compositions of all-trans-retinol: all-trans-13,14-dihydroretinal saturase and methods of use thereof are provided.

Agents for use on skin and/or hair containing quadruply substituted cyclohexene compounds

The invention relates to agents for use on skin or hair, particularly for increasing skin tanning and the synthesis of melanin in skin or hair. The invention contains, in particular, cosmetic or dermatological preparations containing quadruply substituted

Total synthesis of capsanthin and capsorubin using Lewis acid-promoted regio- and stereoselective rearrangement of tetrasubsutituted epoxides

The synthesis of capsanthin 1 and capsorubin 2 was accomplished via the C15-cyclopentyl ketone 6 prepared by Lewis acid-promoted regio- and stereoselective rearrangement of the epoxy dienal 5. The Royal Society of Chemistry.

Synthesis of 10,11,14,15-13C4- and 14,15-13C2-retinyl acetate

The synthesis of 10,11,14,15-13C4- and 14,15-13C2-retinyl acetate is described. The procedure uses a modified Wittig-Horner synthesis. By using the 13C isotope, sensitive gas chromatography-combustion

Stereoselective synthesis and receptor activity of conformationally defined retinoid X receptor selective ligands

Retinoid X Receptor (RXR) specific ligands are currently being investigated for the treatment of metabolic diseases such as type II diabetes. We report the synthesis of conformationally locked retinoids, which are potent RXR selective ligands, and the att

A Novel Method for a Stereoselective Synthesis of Trisubstituted Olefin Using Tricarbonyliron Complex: A Highly Stereoselective Synthesis of (all-E)- and (9Z)-Retinoic Acids

In order to establish the stereoselective synthesis of retinoic acids, which are ligand molecules of the retinoic acid receptors (RARs, all-E-isomer) and the retinoid X receptors (RXRs, 9Z-isomer), the reaction of β-ionone-tricarbonyliron complex 7 with carbanions was investigated. Treatment of 7 with the lithium salt of acetonitrile afforded (7E,9E)-β-ionylideneacetonitrile-tricarbonyliron complex 8 exclusively, via addition, dehydration, and migration of tricarbonyliron complex. On the contrary, the reaction of 7 with the lithium enolate of ethyl acetate and subsequent dehydration by thionyl chloride afforded the ethyl (7E,9Z)-β-ionylideneacetate-tricarbonyliron complex 16b predominantly. These compounds (8 and 16b) were converted to the corresponding β-ionylidene-acetaldehyde-tricarbonyliron complexes (10 and 22) in excellent yields, respectively. The Emmons-Horner reaction of these compounds with C5-phosphonate followed by the sequence of decomplexation and alkaline hydrolysis gave the corresponding retinoic acids (26 and 29).