90107-62-3

Basic information

• Product Name: (2E,4E)-4-Methyl-2,4-hexadienoic Acid Ethyl Ester
• Synonyms: (2E,4E)-4-Methyl-2,4-hexadienoic Acid Ethyl Ester;RCGUDPCNDKMRQV-CUXHJGIESA-N;ethyl 4-methylhexa-2,4-dienoate
• CAS NO: 90107-62-3
• Molecular Formula: C₉H₁₄O₂
• Molecular Weight: 154.20626
• Product Categories: Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 90107-62-3.mol
• Article Data: 16

Chemical Properties

• Appearance: /
• Solubility: Dichloromethane
• CAS DataBase Reference: (2E,4E)-4-Methyl-2,4-hexadienoic Acid Ethyl Ester(CAS DataBase Reference)
• NIST Chemistry Reference: (2E,4E)-4-Methyl-2,4-hexadienoic Acid Ethyl Ester(90107-62-3)
• EPA Substance Registry System: (2E,4E)-4-Methyl-2,4-hexadienoic Acid Ethyl Ester(90107-62-3)

Safety Data

• Hazardous Substances Data: 90107-62-3(Hazardous Substances Data)

Usage

Description

(2E,4E)-4-Methyl-2,4-hexadienoic Acid Ethyl Ester is an organic compound characterized by its double bond configuration and ester functional group. It is a derivative of hexadienoic acid with a methyl group at the 4-position and an ethyl ester group attached to the carboxylic acid. (2E,4E)-4-Methyl-2,4-hexadienoic Acid Ethyl Ester is known for its reactivity and potential applications in the synthesis of various organic compounds.

Uses

Used in Pharmaceutical Industry:
(2E,4E)-4-Methyl-2,4-hexadienoic Acid Ethyl Ester is used as a reactant in the preparation of Quassin (Q509400), a natural product with potential anti-cancer properties. It is also used in the synthesis of Stigmatellin A (S686780), another bioactive compound with potential applications in drug development.
Used in Organic Synthesis:
(2E,4E)-4-Methyl-2,4-hexadienoic Acid Ethyl Ester is used as a building block in the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and other specialty chemicals. Its unique structure and reactivity make it a valuable intermediate in the development of new molecules with specific properties and applications.

Upstream product

• 26526-09-0 4-methylhexa-2,4-dienoic acid 
• 64-17-5 ethanol 
• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 
• 497-03-0 2-methylbut-2-enal 
• 188945-44-0 ethyl 2-[bis(2-isopropylphenoxy)phosphoryl]acetate 
• 6038-09-1 (Z)-2-methyl-2-butenal 
• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 
• 22822-85-1 ethyl sodiodiethylphosphonoacetate 
• 497-03-0 tiglic aldehyde 

Downstream Products

• 1401338-04-2 (2E,4E)-ethyl 7-hydroxy-4-methyl-7-phenylhepta-2,4-dienoate 
• 1401337-53-8 (2E,4E,7S,8R,9S)-ethyl 9-(tert-butyldimethylsilyloxy)-7-hydroxy-4,8-dimethyl-9-phenylnona-2,4-dienoate 
• 1401338-08-6 (2E,4E,7R,8R,9S)-ethyl 9-(tert-butyldimethylsilyloxy)-7-hydroxy-4,8-dimethyl-9-phenylnona-2,4-dienoate 
• 1401337-94-7 (2E,4E,7S,8S,9S)-ethyl 9-(tert-butyldimethylsilyloxy)-7-hydroxy-4,8-dimethyl-9-phenylnona-2,4-dienoate 
• 1401338-79-1 (2E,4E,7R,8S,9S)-ethyl 9-(tert-butyldimethylsilyloxy)-7-hydroxy-4,8-dimethyl-9-phenylnona-2,4-dienoate 
• 1401337-52-7 (2E,4E,7S,8R,9S)-ethyl 7-hydroxy-9-(methoxymethoxy)-4,8-dimethyl-9-phenylnona-2,4-dienoate 
• 1401338-07-5 (2E,4E,7R,8R,9S)-ethyl 7-hydroxy-9-(methoxymethoxy)-4,8-dimethyl-9-phenylnona-2,4-dienoate 
• 1401337-93-6 (2E,4E,7R,8S,9S)-ethyl 7-hydroxy-9-(methoxy-methoxy)-4,8-dimethyl-9-phenylnona-2,4-dienoate 
• 1401338-77-9 (2E,4E,7S,8S,9S)-ethyl 7-hydroxy-9-(methoxymethoxy)-4,8-dimethyl-9-phenylnona-2,4-dienoate 
• 1401337-75-4 (2E,4E,7S,8R,9S)-ethyl 11-(tert-butyldimethylsilyl)-9-(triphenylsilyloxy)-7-hydroxy-4,8-dimethylundeca-2,4-dien-10-ynoate 
• 1401338-46-2 (2E,4E,7R,8R,9S)-ethyl 11-(tert-butyldimethylsilyl)-9-(triphenylsilyloxy)-7-hydroxy-4,8-dimethylundeca-2,4-dien-10-ynoate 
• 76-78-8 d,l-quassin 
• 149494-65-5 (-)-(1β,9β,16β)-20-(tert-butyldiphenylsiloxy)-1,16-dimethoxypicrasan-12-one 
• 149400-40-8 (3R,3aS,5S,6aR,7aS,8R,11R,11aS,11bS,11cS)-11c-(tert-Butyl-diphenyl-silanyloxymethyl)-5,11-dimethoxy-3,8,11a-trimethyl-2-trimethylsilanyloxy-3,3a,4,5,6a,7,7a,8,9,10,11,11a,11b,11c-tetradecahydro-6-oxa-benzo[de]anthracene 

Relevant articles and documents

Step-Economic Synthesis of Biomimetic β-Ketopolyene Thioesters and Demonstration of Their Usefulness in Enzymatic Biosynthesis Studies

Studies on the biosynthetic processing of polyene thioester intermediates are complicated by limited access to appropriate substrate surrogates. We present a step-economic synthetic access to biomimetic β-ketopolyene thioesters that is based on an Ir-catalyzed reductive Horner-Wadsworth-Emmons olefination. New β-ketotriene and pentaenethioates of pantetheine and N-acetylcysteamine were exemplarily synthesized via short and concise routes. The usefulness of these compounds was demonstrated in an in vitro assay with the ketoreductase domain MycKRB from mycolactone biosynthesis.

TRIENETHER COMPOUND, PERFUME COMPOSITION, FOOD AND DRINK PRODUCT AND PERFUMERY AND COSMETIC EACH CONTAINING THEM

PROBLEM TO BE SOLVED: To provide a means capable of imparting unique sweetness and fruit juice feeling suggestive of fruit flesh feeling of mango and a core part of pineapple. SOLUTION: A trienether compound having an isopropenyloxy group as represented by formula (1) is provided. EFFECT: Excellent fruit-like fragrance and flavor with unique sweetness and fruit juice feeling can be imparted by adding the compound represented by formula (1) to food and drink product, and perfumery and cosmetic. SELECTED DRAWING: None COPYRIGHT: (C)2019,JPOandINPIT

Ene-diene transmissive cycloaddition reactions with singlet oxygen: The vinylogous gem effect and its use for polyoxyfunctionalization of dienes

The singlet oxygen reactivities and regioselectivities of the model compounds 1b-d were compared with those of the geminal (gem) selectivity model ethyl tiglate (1a). The kinetic cis effect is kE/kZ = 5.2 for the tiglate/angelate system 1a/1a′ without a change in the high gem regioselectivity. Further conjugation to vinyl groups enabled mode-selective processes, namely, [4 + 2] cycloadditions versus ene reactions. The site-specific effects of methylation on the mode selectivity and the regioselectivity of the ene reaction were studied for dienes 1e-g. A vinylogous gem effect was observed for the γ,δ-dimethylated and α,γ,δ-trimethylated substrates 1h and 1i, respectively. The corresponding phenylated substrates 1j-l showed similar mode selectivity, as monomethylated 1j exhibited exclusively [4 + 2] reactivity while the tandem products 12 and 14 were isolated from the di- and trimethylated substrates 1k and 1l, respectively. The vinylogous gem effect favors the formation of 1,3-dienes from the substrates, and thus, secondary singlet oxygen addition was observed to give hydroperoxy-1,2-dioxenes 19 and 20 in an ene-diene transmissive cycloaddition sequence. These products were reduced to give alcohols (16, 17, and 18) or furans (24 and 25), respectively, or treated with titanium(IV) alkoxides to give the epoxy alcohols 26 and 27. The vinylogous gem effect is rationalized by DFT calculations showing that biradicals are the low-energy intermediates and that no reaction path bifurcations compete.