81581-27-3

Basic information

• Product Name: 3-BENZO[1,3]DIOXOL-5-YL-3-OXO-PROPIONIC ACID ETHYL ESTER
• Synonyms: 3-BENZO[1,3]DIOXOL-5-YL-3-OXO-PROPIONIC ACID ETHYL ESTER;ETHYL 3-(BENZO[D][1,3]DIOXOL-6-YL)-3-OXOPROPANOATE;ETHYL [3,4-(METHYLENEDIOXY)BENZOYL]ACETATE;Ethyl 3-(benzo[d][1,3]dioxol-5-yl)-3-oxopropanoate;ethyl 3-(2H-1,3-benzodioxol-5-yl)-3-oxopropanoate
• CAS NO: 81581-27-3
• Molecular Formula: C₁₂H₁₂O₅
• Molecular Weight: 236.22
• Mol File: 81581-27-3.mol
• Article Data: 22

Chemical Properties

• Melting Point: 42.5 °C
• Boiling Point: 358.8 °C at 760 mmHg
• Flash Point: 197.3 °C
• Appearance: /
• Density: 1.275 g/cm³
• Vapor Pressure: 2.48E-05mmHg at 25°C
• Refractive Index: 1.54
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 10.77±0.20(Predicted)
• CAS DataBase Reference: 3-BENZO[1,3]DIOXOL-5-YL-3-OXO-PROPIONIC ACID ETHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 3-BENZO[1,3]DIOXOL-5-YL-3-OXO-PROPIONIC ACID ETHYL ESTER(81581-27-3)
• EPA Substance Registry System: 3-BENZO[1,3]DIOXOL-5-YL-3-OXO-PROPIONIC ACID ETHYL ESTER(81581-27-3)

Safety Data

• Hazardous Substances Data: 81581-27-3(Hazardous Substances Data)

Usage

General Description

3-Benzo[1,3]dioxol-5-yl-3-oxo-propionic acid ethyl ester is a chemical compound that belongs to the class of dioxolane derivatives. It is an ethyl ester of 3-Benzo[1,3]dioxol-5-yl-3-oxo-propionic acid, which is a synthetic intermediate used in the production of pharmaceuticals and other organic compounds. The chemical structure of 3-Benzo[1,3]dioxol-5-yl-3-oxo-propionic acid ethyl ester contains a dioxolane ring and a propionic acid moiety, making it useful in various organic synthesis reactions. 3-Benzo[1,3]dioxol-5-yl-3-oxo-propionic acid ethyl ester is often used in research and development in the pharmaceutical industry, as well as in academic and industrial laboratories for its potential therapeutic properties and as a building block in the synthesis of more complex molecules.

InChI:InChI=1/C12H12O5/c1-2-15-12(14)6-9(13)8-3-4-10-11(5-8)17-7-16-10/h3-5H,2,6-7H2,1H3

Upstream product

• 25054-53-9 3,4-(methylenedioxy)benzoyl chloride 
• 1007476-32-5 sodium ethyl acetylacetate enolate 
• 326-56-7 methyl 3,4-methylenedioxybenzoate 
• 141-78-6 ethyl acetate 
• 81581-26-2 3,4-Methylendioxybenzoyl-acetessigsaeure-ethylester 
• 94-53-1 Piperonylic acid 
• 37517-78-5 magnesium bis(3-ethoxy-3-oxopropanoate) 
• 623-73-4 diazoacetic acid ethyl ester 
• 120-57-0 piperonal 
• 34023-63-7 ethyl 3-(benzo[d][1,3]dioxol-5-yl)-3-hydroxypropanoate 
• 3162-29-6 1-(benzo[d][1,3]dioxol-6-yl)ethanone 
• 105-58-8 Diethyl carbonate 
• 6148-64-7 ethyl potassium malonate 
• 135696-67-2 piperomylimidazole 

Downstream Products

• 3162-29-6 1-(benzo[d][1,3]dioxol-6-yl)ethanone 
• 207272-65-9 [2-Benzo[1,3]dioxol-5-yl-5-(3,4-dimethoxy-phenyl)-4-hydroxymethyl-furan-3-yl]-methanol 
• 207272-63-7 2-Benzo[1,3]dioxol-5-yl-5-(3,4-dimethoxy-phenyl)-furan-3,4-dicarboxylic acid diethyl ester 
• 207272-61-5 2-(Benzo[1,3]dioxole-5-carbonyl)-3-(3,4-dimethoxy-benzoyl)-succinic acid diethyl ester 
• 146713-95-3 pongapinone A 
• 191677-66-4 (Z)-3-Benzo[1,3]dioxol-5-yl-3-hydroxy-1-[4-hydroxy-2,6-dimethoxy-3-(3-methyl-but-2-enyl)-phenyl]-propenone 
• 191677-62-0 2-(2-Benzo[1,3]dioxol-5-yl-[1,3]dioxolan-2-yl)-1-[4-hydroxy-2,6-dimethoxy-3-(3-methyl-but-2-enyl)-phenyl]-ethanone 
• 191678-09-8 2-(2-Benzo[1,3]dioxol-5-yl-[1,3]dioxolan-2-yl)-1-[8-(tert-butyl-diphenyl-silanyloxy)-5-methoxy-2,2-dimethyl-2H-chromen-6-yl]-ethanol 
• 191677-51-7 2-(2-Benzo[1,3]dioxol-5-yl-[1,3]dioxolan-2-yl)-1-[4-(tert-butyl-diphenyl-silanyloxy)-2,6-dimethoxy-3-(3-methyl-but-2-enyl)-phenyl]-ethanol 
• 191678-11-2 2-(2-Benzo[1,3]dioxol-5-yl-[1,3]dioxolan-2-yl)-1-[8-(tert-butyl-diphenyl-silanyloxy)-5-methoxy-2,2-dimethyl-2H-chromen-6-yl]-ethanone 
• 191677-58-4 2-(2-Benzo[1,3]dioxol-5-yl-[1,3]dioxolan-2-yl)-1-[4-(tert-butyl-diphenyl-silanyloxy)-2,6-dimethoxy-3-(3-methyl-but-2-enyl)-phenyl]-ethanone 
• 112333-50-3 7-(4-methoxyphenyl)-6-(3,4-methylenedioxyphenyl)-1,2,3,4,6,9,9a-octahydroquinolizine 
• 133-03-9 2-exo,6-exo-bis(3',4'-methylenedioxyphenyl)-3,7-dioxabicyclo[3.3.0]octane 
• 112778-68-4 (6R,7S,8R)-5-Oxo-8-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6,7-dicarboxylic acid diethyl ester 

Relevant articles and documents

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Sulfur-controlled and rhodium-catalyzed formal (3 + 3) transannulation of thioacyl carbenes with alk-2-enals and mechanistic insights

A rhodium-catalyzed denitrogenative formal (3 + 3) transannulation of 1,2,3-thiadiazoles with alk-2-enals is achieved, producing 2,3-dihydrothiopyran-4-ones in moderate to excellent yields. An inverse KIE of 0.49 is obtained, suggesting the reversibility of the oxidative addition of thioacyl Rh(i) carbenes to alk-2-enals. The late-stage structural modifications of steroid compounds are realized. Moreover, our studies show that thioacyl carbenes have different reactivities to those of α-oxo and α-imino carbenes, and highlight the importance of heteroatoms in deciding the reactivities of heterovinyl carbenes.

Synthesis of Dithiolethiones and Identification of Potential Neuroprotective Agents via Activation of Nrf2-Driven Antioxidant Enzymes

Oxidative stress is implicated in the pathogenesis of a wide variety of neurodegenerative disorders, and accordingly, dietary supplement of exogenous antioxidants or/and upregulation of the endogenous antioxidant defense system are promising for therapeutic intervention or chemoprevention of neurodegenerative diseases. Nrf2, a master regulator of the cellular antioxidant machinery, cardinally participates in the transcription of cytoprotective genes against oxidative/electrophilic stresses. Herein, we report the synthesis of 59 structurally diverse dithiolethiones and evaluation of their neuroprotection against 6-hydroxydopamine-or H2O2-induced oxidative damages in PC12 cells, a neuron-like rat pheochromocytoma cell line. Initial screening identified compounds 10 and 11 having low cytotoxicity but conferring remarkable protection on PC12 cells from oxidative-mediated damages. Further studies demonstrated that both compounds upregulated a battery of antioxidant genes as well as corresponding genes' products. Significantly, silence of Nrf2 expression abolishes cytoprotection of 10 and 11, indicating targeting Nrf2 activation is pivotal for their cellular functions. Taken together, the two lead compounds discovered here with potent neuroprotective functions against oxidative stress via Nrf2 activation merit further development as therapeutic or chemopreventive candidates for neurodegenerative disorders.