54226-17-4

Basic information

• Product Name: (7E,9Z)-β-Ionylidene Acetaldehyde
• Synonyms: (7E,9Z)-β-Ionylidene Acetaldehyde;(2Z,4E)-3-Methyl-5-(2,6,6-triMethyl-1-cyclohexen-1-yl)-2,4-pentadienal;(Z,E)-3-Methyl-5-(2,6,6-triMethyl-1-cyclohexen-1-yl)-2,4-pentadienal
• CAS NO: 54226-17-4
• Molecular Formula: C₁₅H₂₂O
• Molecular Weight: 218.33458
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals;Retinoids
• Mol File: 54226-17-4.mol
• Article Data: 19

Chemical Properties

• Boiling Point: 329.1±11.0 °C(Predicted)
• Appearance: /
• Density: 0.948±0.06 g/cm3(Predicted)
• Solubility: Acetone, Chloroform, Dichloromethane, Ether, Ethyl Acetate
• CAS DataBase Reference: (7E,9Z)-β-Ionylidene Acetaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: (7E,9Z)-β-Ionylidene Acetaldehyde(54226-17-4)
• EPA Substance Registry System: (7E,9Z)-β-Ionylidene Acetaldehyde(54226-17-4)

Safety Data

• Hazardous Substances Data: 54226-17-4(Hazardous Substances Data)

Usage

Chemical Properties

Yellow Oil

Uses

Intermediate in the preparation of Retinoic Acid derivatives.

Upstream product

• 3917-40-6 (2Z,4E)-3-methyl-5-(2,6,6-trimethylcyclohex-1-enyl)penta-2,4-dienol 
• 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 
• 1224-76-6 9-hydroxy-β-ionylideneacetaldehyde dimethyl acetal 
• 20110-08-1 methyl (2Z,4E)-3-methyl-5-(2,6,6-trimethylcyclohex-1-enyl)penta-2,4-dienoate 
• 56013-12-8 7-cis-β-ionylideneacetaldehyde 
• 62924-18-9 β-ionylidene-acetonitrile 
• 29789-62-6 (2Z,4E)-ethyl 3-methyl-5-(2,6,6-trimethylcyclohex-1-enyl)penta-2,4-dienoate 
• 432-25-7 2,6,6-trimethylcyclohex-1-enecarbaldehyde 
• 114968-77-3 lithio-1 methyl-2 trimethylsiloxy-4 butadiene 
• 303779-99-9 (E)-2-(2,6,6-trimethylcyclohexen-1-yl)-ethenyl (trifluoromethyl)sulfonate 
• 472-66-2 (2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde 
• 6153-05-5 (Z)-3-methylpent-2-en-4-ynol 
• 2408-37-9 2,2,6-trimethylcyclohexan-1-one 

Downstream Products

• 6703-19-1 9Z,11E,13Z-12-carboxyretinoic acid 
• 25529-00-4 6-methyl-8t-(2,6,6-trimethyl-cyclohex-1-enyl)-octa-3t,5c,7-trien-2-one 
• 72903-62-9 (9Z,13Z)-11,12-Dihydro-11-hydroxyretinoic acid δ-lactone 
• 514-85-2 9-cis vitamin A aldehyde 
• 472-86-6 13-cis-vitamin A aldehyde 
• 116-31-4 all-trans-Retinal 
• 25576-26-5 (3Z,5E)-4-methyl-6-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3,5-hexadien-1-yne 
• 131235-61-5 13-demethyl 9-cis-retinoic acid 
• 68-26-8 9-cis-retinol 
• 13312-52-2 9-cis-β-carotene 
• 7235-40-7 beta-carotene 
• 879295-58-6 9-cis-ethyl retinoate 
• 43219-56-3 (1E,3E)-3-methyl-1-[2,6,6-trimethylcyclohex-1-enyl]hexa-1,3,5-triene 
• 115207-29-9 (+/-)-7-hydroxy-3.7-dimethyl-1t-(2.2.6-trimethyl-cyclohexen-⁽⁶⁾-yl)-nonatrien-(1.3t.5t)-oic acid-⁽⁹⁾-ethyl ester 

Relevant articles and documents

METHOD FOR SYNTHESIS OF 9-CIS-BETA-CAROTENE AND FORMULATIONS THEREOF

The present invention relates to a method for total chemical synthesis of 9-cis-β-carotene (9CBC), and further provides stable formulations 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.

Synthesis of 9Z-9-substituted retinoic acids by palladium catalyzed coupling reaction of a vinyl triflate with alkenyl stannanes

Palladium catalyzed cross coupling reactions of a vinyl triflate intermediate and various alkenyl stannanes afforded trisubstituted Z-olefins stereoselectively in high yields. These olefins were then converted to the corresponding 9Z-retinoic acids via Ho