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

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

• 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 
• 432-25-7 2,6,6-trimethylcyclohex-1-enecarbaldehyde 
• 114968-77-3 lithio-1 methyl-2 trimethylsiloxy-4 butadiene 
• 161676-56-8 C₁₅H₂₄O₂ 
• 638-10-8 ethyl 3-methylbut-2-enoate 
• 51318-62-8 ethyl 4-bromo-3-methylcrotonate 
• 14393-37-4 5,4-Dihydro-4-methyl-6-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2H-pyran-2-one 
• 54340-95-3 1,1-diethoxy-3-methyl-3-butene 
• 145572-38-9 1,2-dibromo-4,4-diethoxy-2-methylbutane 
• 145572-39-0 1-bromo-4,4-diethoxy-2-methylbut-1-ene 
• 303779-99-9 (E)-2-(2,6,6-trimethylcyclohexen-1-yl)-ethenyl (trifluoromethyl)sulfonate 
• 29789-62-6 (2Z,4E)-ethyl 3-methyl-5-(2,6,6-trimethylcyclohex-1-enyl)penta-2,4-dienoate 

Downstream Products

• 72903-62-9 (9Z,13Z)-11,12-Dihydro-11-hydroxyretinoic acid δ-lactone 
• 111923-51-4 (3E,5Z,7E)-1,1,1-Trifluoro-6-methyl-8-(2,6,6-trimethyl-cyclohex-1-enyl)-octa-3,5,7-trien-2-one 
• 81176-73-0 11-cis,13-cis-12-carboxyretinoic acid 
• 86708-67-0 ethyl (2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoate 
• 757240-62-3 ethyl 9Z-13-demethylretinoate 
• 68-26-8 9-cis-retinol 
• 13312-52-2 9-cis-β-carotene 
• 25529-00-4 6-methyl-8t-(2,6,6-trimethyl-cyclohex-1-enyl)-octa-3t,5c,7-trien-2-one 
• 17974-57-1 (3E,5E,7E)-6-methyl-8-(2,6,6-trimethyl-1-cyclohexenyl)-3,5,7-octatriene-2-one 
• 302-79-4 9,13-di-cis-retinoic acid 
• 302-79-4 9-cis-retinoic acid 
• 6703-19-1 9Z,11E,13Z-12-carboxyretinoic acid 
• 514-85-2 9-cis vitamin A aldehyde 
• 472-86-6 13-cis-vitamin A aldehyde 

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.

A cross-metathesis approach to the synthesis of new etretinate type retinoids, ethyl retinoate and its 9Z-isomer

Two aromatic retinoids were synthesized from styrene derivatives using a novel strategy with a cross-metathesis reaction as a key step. The biological activity of the new etretinate analogues was tested. Cross-metathesis reactions were also employed for the preparation of ethyl retinoate and its 9Z-isomer via the C15 + C5 route.

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 and biological activity of 13-substituted retinoic acids

13-Demethyl or 13-substituted all-E- and 9Z-retinoic acids were synthesized using a palladium-catalyzed coupling reaction of enol triflates and tributylstannylolefins. Their biological activities were then measured. The 13-ethyl analogs exhibited approximately one-half of the antiproliferative and differentiation-inducing activity of ATRA in HL-60 cells. In contrast, in the 9Z-derivatives, all analogs, except for the 13-butyl derivatives, showed apoptosis-inducing activity.

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

Stereoselective synthesis of 9-cis-retinoic acid by Suzuki reaction

The entire polyenic side chain of ethyl 9-cis-retinoate (7) has been stereoselectively synthesized and attached to the hydrophobic ring by a high-yielding thallium-accelerated Suzuki cross-coupling reaction. The Suzuki reaction partners, tetraenyl iodide 18 and alkenyl organoborane 19, are more conveniently used immediately after generation from their precursors. Alternative approaches using either the Stille reaction or a Suzuki reaction with a shorter polyenic component proved less efficient. The highly convergent sequence can be adapted to the preparation of analogs of 9-cis-retinoic acid (2), the natural ligand for the retinoid X (RXR) subfamily of nuclear receptors.

Synthesis of a new phospholipase A2 inhibitor of an aldehyde terpenoid and its possible inhibitory mechanism

3-(E)Methoxycarbonyl-2,4,6-trienal compound A was stereoselectively synthesized and found to show strong inhibitory activity toward phospholipase A2 (PLA2) from bovine pancreas. As the inhibitory mechanism of PLA2 by A, the irreversible formation of dihydropyridine resulting from the reaction of A with lysine residues in PLA2 is proposed based on the model reactions.

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).

Stereoselective synthesis of 7E,9E- and 7E,9Z-β-ionylidene-acetaldehydes by use of tricarbonyl iron complex

Stereoselective synthesis of 7E,9E- and 7E,9Z-β-ionylideneacetaldehydes was accomplished from the β-ionone tricarbonyl iron complex, and the latter was converted to 9Z-retinoic acid.