20638-89-5

Basic information

• Product Name: 13-cis-Retinonitrile
• Synonyms: 13-cis-Retinonitrile;(2E,4E,6E,8Z)-3,7-DiMethyl-9-(2,6,6-triMethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenenitrile
• CAS NO: 20638-89-5
• Molecular Formula: C₂₀H₂₇N
• Molecular Weight: 281
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals;Retinoids
• Mol File: 20638-89-5.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 13-cis-Retinonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 13-cis-Retinonitrile(20638-89-5)
• EPA Substance Registry System: 13-cis-Retinonitrile(20638-89-5)

Safety Data

• Hazardous Substances Data: 20638-89-5(Hazardous Substances Data)

Usage

Uses

An isomer of an all-trans-Retinal intermediate

Upstream product

• 94875-99-7 (4E,6E,8E)-7-Methyl-3-methylene-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-4,6,8-trienenitrile 
• 1856-64-0 2-Cyan-Vitamin-A-saeure 
• 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 
• 19834-52-7 3-Methyl-1-(2,6,6-trimethyl-cyclohexen-⁽¹⁾-yl)-pentadien-(1,3)-saeure-⁽⁵⁾-nitril 
• 1209-68-3 3-methyl-5-(2,6,6-trimethylcyclohex-1-enyl)penta-2, 4-dienal 
• 1856-64-0 C₂₁H₂₇NO₂ 
• 20638-88-4 9-trans-13-trans-dimethyl-7-(1,1,5-trimethyl-5-cyclohexen-6-yl)-7,9,11,13-nonatetraene-15-nitrile 
• 102935-64-8 9,14-dihydroxy-9,13-dimethyl-7-(1,1,5-trimethyl-5-cyclohexen-6-yl)-10,12-nonadiene-15-nitrile 
• 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 
• 2537-48-6 diethyl 1-cyanomethylphosphonate 
• 76929-15-2 (5Z,7E)-6-Methyl-8-(2,6,6-trimethyl-cyclohex-1-enyl)-octa-5,7-dien-3-yn-2-ol 
• 54226-17-4 (2Z,4E)-3-methyl-5-[2,6,6-trimethylcyclohex-1-enyl]penta-2,4-dienal 

Downstream Products

• 116-31-4 all-trans-Retinal 
• 87391-97-7 <15-13C>13-cis-retinal 
• 78508-47-1 C₁₉⁽¹³⁾CH₂₈O 
• 99302-30-4 retinal 
• 99302-31-5 retinal 
• 472-86-6 13-cis-vitamin A aldehyde 
• 7235-40-7 beta-carotene 
• 1436-55-1 3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenal 

Relevant articles and documents

SOLVENT DEPENDENT PHOTOISOMERIZATION OF POLYENE NITRILES

The initial product ratio of several polyene nitriles, wich do not have low lying n,?* states, are reported.The solvent dependent chemistry has been discussed in conjunction with the well known retinal chemistry.

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.

Preparation of (9Z, 11Z) - Vitamin A

Starting from (7E,9Z)-C15-aldehyde 4, the syntheses of (9Z, 11Z)-vitamin A acetate and palmitate are reported. The construction strategy is based on treatment of 4 with Zn-PPh3/CBr4, addition of acetaldehyde followed by a