20638-88-4

Basic information

• Product Name: all-trans-Retinonitrile
• Synonyms: all-trans-Retinonitrile;(2E,4E,6E,8E)-3,7-DiMethyl-9-(2,6,6-triMethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenenitrile;all-trans-VitaMin A Nitrile
• CAS NO: 20638-88-4
• Molecular Formula: C₂₀H₂₇N
• Molecular Weight: 281
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals;Retinoids
• Mol File: 20638-88-4.mol
• Article Data: 15

Chemical Properties

• Appearance: /
• CAS DataBase Reference: all-trans-Retinonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: all-trans-Retinonitrile(20638-88-4)
• EPA Substance Registry System: all-trans-Retinonitrile(20638-88-4)

Safety Data

• Hazardous Substances Data: 20638-88-4(Hazardous Substances Data)

Usage

Uses

Retinal intermediate.

Upstream product

• 17974-57-1 (3E,5E,7E)-6-methyl-8-(2,6,6-trimethyl-1-cyclohexenyl)-3,5,7-octatriene-2-one 
• 372-09-8 cyanoacetic acid 
• 116-31-4 all-trans-Retinal 
• 102935-64-8 9,14-dihydroxy-9,13-dimethyl-7-(1,1,5-trimethyl-5-cyclohexen-6-yl)-10,12-nonadiene-15-nitrile 
• 67890-46-4 all-trans-retinaldoxime 
• 3917-41-7 (2E,4E)-3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienal 
• 105175-91-5 3-methyl-5-(2’,6’,6’-trimethylcyclohex-1’-en-1’-yl)-penta-2,4-dienenitrile 
• 110875-15-5 (4E,6E,8E)-3,7-dimethyl-3-hydroxy-9-(2,6,6-trimethyl-1-cyclohexenyl)-4,6,8-nonatrienenitrile 
• 79-77-6 (E)-β-ionone 
• 5299-98-9 (2E,4E)-3-methyl-5-(2,6,6-trimethyl-cyclohex-1-enyl)-penta-2,4-dienenitrile 
• 1856-64-0 2-Cyan-Vitamin-A-saeure 
• 94875-99-7 (4E,6E,8E)-7-Methyl-3-methylene-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-4,6,8-trienenitrile 
• 1220-77-5 6-methyl-8-(2,6,6-trimethyl-1-cyclohexenyl)-3,5,7-octatriene-2-one 
• 79-77-6 4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-buten-2-one 

Downstream Products

• 472-86-6 13-cis-vitamin A aldehyde 
• 116-31-4 all-trans-Retinal 
• 6985-27-9 β-apo-14'-carotenal 
• 1856-68-4 Retinyliden-malonsaeure-mononitril 
• 1436-55-1 3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenal 
• 339-16-2 all-trans-methyl retinoate 
• 53121-25-8 all-trans-14-methyl-retinal 
• 7235-40-7 beta-carotene 
• 330808-45-2 3,7-dimethyl-2-iodo-9-(2',6',6'-trimethyl-1'-cyclohexen-1'-yl)-2,4,6,8-nonatetraenenitrile 
• 99302-31-5 retinal 
• 99302-30-4 retinal 
• 87391-97-7 <15-13C>13-cis-retinal 
• 78508-47-1 C₁₉⁽¹³⁾CH₂₈O 
• 20638-90-8 (2E,4E,6Z,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraenenitrile 

Relevant articles and documents

COMPOUNDS AND METHODS OF TREATING OCULAR DISORDERS

A method of treating an ocular disorder in a subject associated with increased all-trans-retinal in an ocular tissue includes administering to the subject a therapeutically effective amount of a primary amine compound of formula (I); and pharmaceutically acceptable salts thereof.

New syntheses of retinal and its acyclic analog γ-retinal by an extended aldol reaction with a C6 building block that incorporates a C5 unit after decarboxylation. A formal route to lycopene and β-carotene

Since the C15 β-end-group aldehyde 10 ((β-ionylidene) acetaldehyde), an excellent intermediate in the syntheses of retinoids, can be synthesized in many ways from β-ionone, and since the corresponding acyclic C15 ψ-end-group aldehyde 5 can easily be synthesized from citral (1) (Scheme 3), we applied the C15 + C5 route to the syntheses of γ-retinal ((all-E)-8) (Scheme 3) and retinal ((all-E)-13) (Scheme 4), and therefore, by coupling (2 x C20 → C 40), to the preparation of lycopene (14) and β-carotene (15) (Scheme 5). Our new syntheses of retinal ((all-E)-13) and γ-retinal ((all-E)-8 use an extended aldol reaction with a C6 building block that incorporates a C5 unit after decarboxylation.

Rhenium(VII) oxo complexes as extremely active catalysts in the dehydration of primary amides and aldoximes to nitriles

An economical and environmentally benign process for the preparation of nitriles by the dehydration of primary amides and aldoximes is catalyzed by rhenium(VII) oxo complexes such as perrhenic acid and trimethylsilylperrhenate (see scheme). The reaction proceeds at azeotropic reflux (with the removal of water) under essentially neutral conditions.