84736-28-7

Basic information

• Product Name: (3Z)-4-(1,3-benzodioxol-5-yl)-3-(methoxycarbonyl)but-3-enoic acid
• CAS NO: 84736-28-7
• Molecular Formula: C₁₃H₁₂O₆
• Molecular Weight: 264.2308
• Mol File: 84736-28-7.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 448°C at 760 mmHg
• Flash Point: 173°C
• Density: 1.397g/cm³
• Vapor Pressure: 8.21E-09mmHg at 25°C
• Refractive Index: 1.608
• CAS DataBase Reference: (3Z)-4-(1,3-benzodioxol-5-yl)-3-(methoxycarbonyl)but-3-enoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (3Z)-4-(1,3-benzodioxol-5-yl)-3-(methoxycarbonyl)but-3-enoic acid(84736-28-7)
• EPA Substance Registry System: (3Z)-4-(1,3-benzodioxol-5-yl)-3-(methoxycarbonyl)but-3-enoic acid(84736-28-7)

Safety Data

• Hazardous Substances Data: 84736-28-7(Hazardous Substances Data)

Usage

Description

(3Z)-4-(1,3-benzodioxol-5-yl)-3-(methoxycarbonyl)but-3-enoic acid is a complex chemical compound that features a 1,3-benzodioxol-5-yl group and a methoxycarbonyl group attached to a butenoic acid backbone. The (3Z) configuration in its name specifies the geometric arrangement of the double bond within the molecule, which is crucial for its potential reactivity and interactions with other molecules.

Uses

Used in Medicinal Chemistry:
(3Z)-4-(1,3-benzodioxol-5-yl)-3-(methoxycarbonyl)but-3-enoic acid is used as a building block or intermediate in the synthesis of pharmaceutical compounds due to its unique structural features and functional groups. Its presence of the 1,3-benzodioxol-5-yl and methoxycarbonyl groups may contribute to the compound's ability to form specific interactions with biological targets, making it a promising candidate for drug development.
Used in Drug Development:
In the pharmaceutical industry, (3Z)-4-(1,3-benzodioxol-5-yl)-3-(methoxycarbonyl)but-3-enoic acid may be utilized as a precursor or key component in the creation of new drugs. Its structural complexity and the presence of the double bond in the (3Z) configuration could be leveraged to design molecules with specific biological activities, potentially leading to the development of novel therapeutic agents.
Further research and analysis of (3Z)-4-(1,3-benzodioxol-5-yl)-3-(methoxycarbonyl)but-3-enoic acid are necessary to fully understand its potential applications and benefits in the fields of medicinal chemistry and drug development. Its unique structural features and functional groups may offer new avenues for the treatment of various diseases and conditions.

Upstream product

• 120-57-0 piperonal 
• 124-41-4 sodium methylate 
• 123-25-1 succinic acid diethyl ester 
• 15930-53-7 6-bromo-3,4-methylenedioxybenzaldehyde 
• 106-65-0 Dimethyl succinate 

Downstream Products

• 17187-79-0 (E)-4-(benzo[d][1,3]dioxol-5-ylmethyl)-3-(3,4,5-trimethoxybenzylidene)dihydrofuran-2(3H)-one 
• 108146-55-0 (E)-3-(3,4,5-trimethoxybenzylidene)-4-((benzo-[d][1,3]dioxol-5-yl)methyl)dihydrofuran-2(3H)-one 
• 17187-78-9 (R)-4-Benzo[1,3]dioxol-5-ylmethyl-3-[hydroxy-(3,4,5-trimethoxy-phenyl)-methyl]-dihydro-furan-2-one 
• 17187-78-9 (S)-4-Benzo[1,3]dioxol-5-ylmethyl-3-[hydroxy-(3,4,5-trimethoxy-phenyl)-methyl]-dihydro-furan-2-one 
• 72690-16-5 (3S,4S)-4-(benzo[d][1,3]dioxol-5-ylmethyl)-3-(3,4,5-trimethoxybenzyl)dihydrofuran-2(3H)-one 
• 144539-72-0 4-Benzo[1,3]dioxol-5-ylmethyl-3-[hydroxy-(3,4,5-trimethoxy-phenyl)-methyl]-dihydro-furan-2-one 

Relevant articles and documents

Design, synthesis, and in vitro antiplatelet aggregation activities of taiwanin C

Total synthesis of taiwanin C was realised efficiently in a global yield of 52%. Taiwanin C in aggregation assays inhibited platelet aggregation in a concentration-dependent manner with an IC50 of 0.46 μM after exposure of human platelet to AA. Similarly, to AA, taiwanin C inhibited significantly TRAP-6-induced platelet aggregation with IC50 of 0.56 μM. Molecular docking studies were carried out using the molecular target the COX-1, COX-2 and PAR-1 proteins. These studies suggest that taiwanin inhibits COX-1 more strongly than COX-2. Taiwanin C showed better antiplatelet action in the presence of TRAP-6 than indomethacin and molecular docking studies suggest different mechanisms of action for the two compounds on PAR-1. These results demonstrate that taiwanin C acts very efficiently in two different signaling pathways of platelet aggregation. Although preliminary, these results indicate that taiwanin C has potential for further studies on its use for the development of new antiplatelet.

Design and synthesis of novel arctigenin analogues for the amelioration of metabolic disorders

Analogues of the natural product (-)-arctigenin, an activator of adenosine monophosphate activated protein kinase, were prepared in order to evaluate their effects on 2-deoxyglucose uptake in L6 myotubes and possible use in ameliorating metabolic disorders. Racemic arctigenin 2a was found to display a similar uptake enhancement as does (-)-arctigenin. As a result, the SAR study was conducted utilizing racemic compounds. The structure-activity relationship study led to the discovery of key substitution patterns on the lactone motif that govern 2-deoxyglucose uptake activities. The results show that replacement of the para-hydroxyl group of the C-2 benzyl moiety of arctigenin by Cl has a pronounced effect on uptake activity. Specifically, analogue 2p, which contains the p-Cl substituent, stimulates glucose uptake and fatty acid oxidation in L6 myotubes.