419534-29-5

Basic information

• Product Name: (4E)-5-(4-Methoxy-2,3,6-trimethylphenyl)-3-methyl-2,4-pentadienal
• Synonyms: (4E)-5-(4-Methoxy-2,3,6-trimethylphenyl)-3-methyl-2,4-pentadienal;(4E)-5-(4-Methoxy-2,3,6-triMethylphenyl)-3-Methyl-2,4-pentadienal (cis/trans Mixture)
• CAS NO: 419534-29-5
• Molecular Formula: C16H20O2
• Molecular Weight: 244.33
• Product Categories: Aromatics Compounds;Aromatics
• Mol File: 419534-29-5.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• Storage Temp.: Amber Vial, -86°C Freezer, Under Inert Atmosphere
• Solubility: Acetone, Chloroform, Dichloromethane, Ethyl Acetate, Hexane, Methanol
• CAS DataBase Reference: (4E)-5-(4-Methoxy-2,3,6-trimethylphenyl)-3-methyl-2,4-pentadienal(CAS DataBase Reference)
• NIST Chemistry Reference: (4E)-5-(4-Methoxy-2,3,6-trimethylphenyl)-3-methyl-2,4-pentadienal(419534-29-5)
• EPA Substance Registry System: (4E)-5-(4-Methoxy-2,3,6-trimethylphenyl)-3-methyl-2,4-pentadienal(419534-29-5)

Safety Data

• Hazardous Substances Data: 419534-29-5(Hazardous Substances Data)

Usage

Description

(4E)-5-(4-Methoxy-2,3,6-trimethylphenyl)-3-methyl-2,4-pentadienal is a pale yellow solid that serves as an intermediate in the synthesis of aromatic analogs of retinal and retinoic acid. It is a complex organic molecule with a unique structure that contributes to its specific applications in the chemical and pharmaceutical industries.

Uses

Used in Pharmaceutical Industry:
(4E)-5-(4-Methoxy-2,3,6-trimethylphenyl)-3-methyl-2,4-pentadienal is used as an intermediate for the synthesis of aromatic analogs of retinal and retinoic acid. These analogs are essential in the development of treatments for various medical conditions, including vision-related disorders and other health issues that can be addressed through the modulation of retinal and retinoic acid pathways.
Used in Chemical Industry:
In the chemical industry, (4E)-5-(4-Methoxy-2,3,6-trimethylphenyl)-3-methyl-2,4-pentadienal is used as a key intermediate in the synthesis of various aromatic compounds. Its unique structure allows for the creation of a wide range of products with different applications, such as fragrances, dyes, and other specialty chemicals.

Upstream product

• 63650-98-6 5-(4-methoxy-2,3,6-trimethylphenyl)-3-methylpenta-2,4-dien-1-ol 
• 167637-41-4 ethyl 3-methyl-5-(4'-methoxy-2',3',6'-trimethylphenyl)-2,4-pentadienoate 
• 54757-47-0 4-(4'-methoxy-2',3',6'-trimethylphenyl)-but-3-ene-2-one 
• 54344-92-2 2,3,6-trimethyl-4-methoxy-benzaldehyde 
• 697-82-5 2,3,5-trimethylphenol 
• 20469-61-8 2,3,5-trimethylanisole 
• 167637-42-5 5-(4'-methoxy-2',3',6'-trimethylphenyl)-3-methylpenta-2,4-dienol 
• 51318-62-8 ethyl (E)-4-bromo-3-methyl-2-butenoate 
• 41891-54-7 diethyl 3-(ethoxycarbonyl)-3-methylprop-2-en-yl phosphate 
• 65527-85-7 ethyl (E)-4-hydroxy-3-methyl-2-butenoate 
• 1269259-99-5 (2E,4E)-ethyl 5-(-4-methoxy-2,3,6-trimethylphenyl)-3-methylpenta-2,4-dienoate 
• 3621-52-1 (E)-ethyl 4-chloro-3-methylbut-2-enoate 
• 154152-57-5 4-bromo-3-nitro-1,2,5-trimethylbenzene 
• 478496-92-3 2-[(1E)-3-(2,2-dimethoxyethyl)buta-1,3-dienyl]-5-methoxy-1,3,4-trimethylbenzene 

Downstream Products

• 54350-48-0 etretinate 
• 1621283-97-3 4,4’-((1E,3E,5E,7E,9E,11E,13E)-3,7,12-trimethyltetradeca-1,3,5,7,9,11,13-heptaene-1,14-diyl)bis(1-methoxy-2,3,5-trimethylphenol) 
• 1621284-01-2 4,4’-((1E,3E,5E,7E,9E,11E,13E)-3,7,12-trimethyltetradeca-1,3,5,7,9,11,13-heptaene-1,14-diyl)bis(1-methoxy-2,3,5-trimethylbenzene) 
• 1621283-96-2 4,4’-((1E,3E,5E,7E,9E)-3,8-dimethyldeca-1,3,5,7,9-pentaene-1,10-diyl)bis(2,3,5-trimethylphenol) 
• 1621284-00-1 4,4’-((1E,3E,5E,7E,9E)-3,8-dimethyldeca-1,3,5,7,9-pentaene-1,10-diyl)bis(1-methoxy-2,3,5-trimethylbenzene) 
• 63650-94-2 9-(4-methoxy-2,3,6-trimethylphenyl)-2-fluoro-3,7-dimethyl-2(Z),4(E),6(E),8(E)-nonatetraenoic acid ethyl ester 
• 63651-29-6 (2E,4E,6E,8E)-9-(4-Methoxy-2,3,6-trimethyl-phenyl)-7-methyl-3-trifluoromethyl-nona-2,4,6,8-tetraenoic acid ethyl ester 
• 63651-10-5 (2E,4E,6E,8E)-4-Fluoro-9-(4-methoxy-2,3,6-trimethyl-phenyl)-3,7-dimethyl-nona-2,4,6,8-tetraenoic acid ethyl ester 
• 63700-90-3 9-(4-methoxy-2,3,6-trimethylphenyl)-4-fluoro-3,7-dimethyl-2(E),4(E),6(E),8(E)-nonatetraenoic acid ethyl ester 
• 63650-95-3 (2Z,4E,6Z,8E)-2-Fluoro-9-(4-methoxy-2,3,6-trimethyl-phenyl)-3,7-dimethyl-nona-2,4,6,8-tetraenoic acid ethyl ester 
• 63651-18-3 7-(4-methoxy-2,3,6-trimethylphenyl)-2-fluoro-5-methyl-2(Z),4(E),6(E)-heptatrienoic acid, ethyl ester 

Relevant articles and documents

Tailoring 3,3'-dihydroxyisorenieratene to hydroxystilbene: Finding a resveratrol analogue with increased antiproliferation activity and cell selectivity

Four novel compounds were designed by "tailoring" 3,3'-dihydroxyisorenieratene (a natural carotenoid) based on an isoprene unit retention truncation strategy. Among them, the smallest molecule 1 (2,3,6,2',3',6'-hexamethyl-4,4'-dihydroxy-trans-stilbene) was concisely synthesized in a one-pot Stille-Heck tandem sequence, and surfaced as a promising lead molecule in terms of its selective antiproliferative activity mediated by blocking the NCI-H460 cell cycle in G1 phase. Additionally, theoretical calculations and cell uptake experiments indicate that the unique polymethylation pattern of compound 1 significantly induces a conformational change shift out of planarity and increases its cell uptake and metabolic stability. The observation should be helpful to rationally design resveratrol-inspired antiproliferative agents. Four novel compounds were designed by "tailoring" 3,3'-dihydroxyisorenieratene (a natural carotenoid) based on an isoprene unit retention truncation strategy. Among them, the smallest molecule 1 was concisely synthesized by a one-pot Stille-Heck tandem sequence, and surfaced as a promising lead molecule in terms of its selective antiproliferative activity (see figure).

A new stereoselective synthesis of acitretin (=Soriatane, Neotigason)

A new synthesis of acitretin via a C15 + C5 route is reported. The C15 unit is the key step, involving a procedure that provides the required (all-E)-C15-aldehyde with high stereoselectivity.

STEREOSELECTIVE SYNTHESIS OF 5-ARYL-3-METHYL-2E,4E-PENTADIENALS

A series of 5-aryl-3-methyl-2E,4E-pentadienals were synthesized stereoselectively from 4-aryl-3E-buten-2-ones and methylmagnesium iodide followed by formylation of the obtained tertiary dimethylstyrylcarbinols by the formylating complex produced from dimethylformamide and phosphorus oxychloride.A synthesis of 2,3,6-trimethyl-4-methoxybenzaldehyde, starting from pseudocumene, is proposed.