17974-55-9

Basic information

• Product Name: 2,4-Pentadienoic acid, 3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-, ethyl ester, (2E,4E)-
• CAS NO: 17974-55-9
• Molecular Formula: C17H26O2
• Molecular Weight: 262.392
• Mol File: 17974-55-9.mol
• Article Data: 11

Chemical Properties

• CAS DataBase Reference: 2,4-Pentadienoic acid, 3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-, ethyl ester, (2E,4E)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-Pentadienoic acid, 3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-, ethyl ester, (2E,4E)-(17974-55-9)
• EPA Substance Registry System: 2,4-Pentadienoic acid, 3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-, ethyl ester, (2E,4E)-(17974-55-9)

Safety Data

• Hazardous Substances Data: 17974-55-9(Hazardous Substances Data)

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 
• 105-36-2 ethyl bromoacetate 
• 927-80-0 1-ethoxyacetylene 
• 174836-75-0 (E)-5-(2,6,6-Trimethyl-cyclohex-1-enyl)-pent-4-en-2-ynoic acid ethyl ester 
• 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 
• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 
• 69445-88-1 (triethyl-λ⁵-phosphanylidene)-acetic acid ethyl ester 

Downstream Products

• 14398-42-6 (2E,4E)-3-methyl-5-(2,6,6-trimethylcyclohex-1-enyl)penta-2,4-dienoic acid 
• 3917-39-3 (2E,4E)-3-methyl-5-(2,6,6-trimethyl-1-cyclohexenyl)-2,4-pentadien-1-ol 
• 3917-41-7 (2E,4E)-3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienal 
• 17974-57-1 (3E,5E,7E)-6-methyl-8-(2,6,6-trimethyl-1-cyclohexenyl)-3,5,7-octatriene-2-one 
• 347384-09-2 14,15-¹³C₂-retinoic acid ethyl ester 
• 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 

Relevant articles and documents

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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.

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.

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.