2815-95-4

Basic information

• Product Name: 3-(3,4-METHYLENEDIOXYPHENYL)PROPIONIC ACID
• Synonyms: 1,3-BENZODIOXOLE-5-PROPANOIC ACID;3-(3,4-METHYLENEDIOXYPHENYL)PROPIONIC ACID;3-(1,3-BENZODIOXOL-5-YL)PROPANOIC ACID;3,4-METHYLENEDIOXYDIHYDROCINNAMIC ACID;3,4-(METHYLENEDIOXY)HYDROCINNAMIC ACID;PIPERONYL ACETIC ACID;TIMTEC-BB SBB000324;3,4-(methylenedioxy)-hydrocinnamicaci
• CAS NO: 2815-95-4
• Molecular Formula: C₁₀H₁₀O₄
• Molecular Weight: 194.18
• EINECS: 220-565-9
• Product Categories: Aromatic Propionic Acids;Aromatics;Heterocycles
• Mol File: 2815-95-4.mol
• Article Data: 29

Chemical Properties

• Melting Point: 86-88°C
• Boiling Point: 349℃
• Flash Point: 142℃
• Appearance: /
• Density: 1.343
• Vapor Pressure: 1.81E-05mmHg at 25°C
• Storage Temp.: 2-8°C
• Solubility: Soluble in chloroform and ethyl acetate.
• PKA: 4.59±0.10(Predicted)
• BRN: 181735
• CAS DataBase Reference: 3-(3,4-METHYLENEDIOXYPHENYL)PROPIONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(3,4-METHYLENEDIOXYPHENYL)PROPIONIC ACID(2815-95-4)
• EPA Substance Registry System: 3-(3,4-METHYLENEDIOXYPHENYL)PROPIONIC ACID(2815-95-4)

Safety Data

• Hazard Codes: Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36/37/39
• WGK Germany: 2
• RTECS: MW5600000
• HazardClass: IRRITANT
• Hazardous Substances Data: 2815-95-4(Hazardous Substances Data)

Usage

Chemical Properties

Grey Solid

Uses

Substituted cinnamic and dihydrocinnamic acids show anti-inflammatory and analgesic activity, with cinnamic acids being more biologically active.

InChI:InChI=1/C10H10O4/c11-10(12)4-2-7-1-3-8-9(5-7)14-6-13-8/h1,3,5H,2,4,6H2,(H,11,12)/p-1

Upstream product

• 136507-21-6 3-benzo[1,3]dioxol-5-yl-propionic acid methylamide 
• 2373-80-0 3,4-methylenedioxy-trans-cinnamic acid 
• 1162198-85-7 (Z)-2-acetoxy-3-(3,4-methylenedioxyphenyl)acrylic acid 
• 120-57-0 piperonal 
• 141-82-2 malonic acid 
• 143815-53-6 C₁₀H₈O₅ 
• 38243-40-2 β-(benzo[1,3]dioxol-5-yl)-α-acetamidoacrylic acid 
• 14731-78-3 ethyl 3,4-methylenedioxycinnamate 
• 139-85-5 3,4-dihydroxybenzaldehyde 
• 74402-06-5 2-benzo[1,3]dioxol-5-ylmethylmalonic acid dimethyl ester 
• 20850-43-5 5-(chloromethyl)-1,3-benzodioxole 
• 22180-30-9 Diethyl α-piperonylmalonate 
• 24393-66-6 ethyl (E)-3-(benzo[d][1,3]dioxol-5-yl)acrylate 
• 7315-32-4 5-vinyl-1,3-benzodioxole 

Downstream Products

• 7116-48-5 3-benzo[1,3]dioxol-5-yl-propionic acid ethyl ester 
• 6412-87-9 5,6-methylenedioxy-1-indanone 
• 108937-09-3 3-Benzo[1,3]dioxol-5-yl-N-[2-(2-benzyloxy-3-methoxy-phenyl)-ethyl]-propionamide 
• 114363-10-9 N-2-(3-benzyloxy-4-methoxyphenyl)ethyl-3-(3',4'-methylenedioxyphenyl)propionamide 
• 156488-61-8 3-(3,4-methylenedioxyphenyl)-N-(3,4-dimethoxyphenethyl)propionamide 
• 139747-16-3 2-piperonyl-3-(3,4,5-trimethoxy-benzyl)-succinic acid 
• 183853-60-3 (R)-3-(3-Benzo[1,3]dioxol-5-yl-propionyl)-4-benzyl-oxazolidin-2-one 
• 33543-11-2 N-[3-(1,3-benzodioxol-5-yl)propyl]-N-methylamine 
• 1400221-87-5 N-((R)-3-benzylthio-1-methoxy-1-oxo-2-propanyl)-3-((3,4-methylenedioxy)phenyl)propanamide 

Relevant articles and documents

Synthesis method and application of cubebin

The invention discloses a synthesis method of cubebin, which comprises the following steps: using 1,3-benzodioxole-5-carboxaldehyde and malonic acid as initial raw materials to generate 1,3-benzodioxole-5-propanoic acid, reacting the 1,3-benzodioxole-5-propanoic acid with oxalyl chloride to generate 1,3-benzodioxole-5-propionyl chloride, then reacting the 1,3-benzodioxole-5-propionyl chloride with (S)-4-benzyl-2-oxazolidinone to generate corresponding amide, reacting a product with bromopropyl to generate corresponding olefin, generating a corresponding carbonyl compound under the catalysis of a combined oxidant OsO4/NMO, using the carbonyl compound to prepare a corresponding hydroxyl compound, oxidizing the hydroxyl compound into a lactone compound by using a Fetizon reagent, reacting the lactone compound with 5-(bromomethyl)-1,3-benzodioxole, and finally, reducing the product by using diisobutylaluminium hydride to obtain cubebin. The invention further discloses application of cubebin in sedative and peaceful sleep. The invention provides a potential therapeutic drug for calming and sleeping.

Design, synthesis, trypanocidal activity, and studies on human albumin interaction of novel s-alkyl-1,2,4-triazoles

Chagas disease is a neglected tropical disease caused by the hemoflagellated parasite Trypanosoma cruzi (Kinetoplastida). The only available drug to treat chagasic patients in Brazil, the nitroheterocycle benznidazole, is effective solely during the acute phase of the infection. There is accordingly a need to develop new therapeutic tools for the treatment of Chagas disease. This work reports the synthesis, trypanocidal evaluation and human serum albumin (HSA) interactions of a novel series of 1,2,4-triazoles. The new derivatives were synthesized via microwave irradiation in good yields. Most compounds showed toxic effects against T. cruzi with low toxicity to host cells. Three S-alkylated-triazoles showed the best activity profile against amastigotes, with half maximal inhibitory concentration (IC50) values of 3.95 ± 1.41, 4.15 ± 0.92 and 3.61 ± 0.65 μmol L-1, respectively. The interaction between HSA and 3-[(1E,3E)-4-(1,3-benzodioxol-5-yl)buta-1,3-dien-1-yl]-5-(butylthio)-4-cyclohexyl-4,5-dihydro-1H-1,2,4-triazole was investigated using multiple spectroscopic techniques and molecular docking, revealing that serum albumin is a potential endogenous carrier to this compound in the human bloodstream.

Total Synthesis and Evaluation of B-Homo Palmatine and Berberine Derivatives as p300 Histone Acetyltransferase Inhibitors

Palmatine and berberine, structurally similar isoquinoline alkaloids exhibiting a broad range of biological activities, were recently found to inhibit p300 histone acetyltransferase (HAT), a potential therapeutic target for treating transcriptional activator-driven malignancies and diseases. Here, we report the first total synthesis of B-homo palmatine (11a) and berberine (11b) derivatives, which were synthesized from 3,4-dimethoxybenzaldehyde (1a) and benzo[d][1,3]dioxole-5-carbaldehyde (1b) in nine steps in 13.8 and 16.9 % overall yields, respectively. A number of other new B-homo palmatine and berberine derivatives were also prepared. These derivatives display good inhibitory activity against p300 HAT; compound 12a manifests the most potent inhibition with an IC50 value of 0.42 μm. Cell-based assays revealed that 12a exhibits certain inhibitory activity against HCG27, HT1080, and Z-138 cell lines, and no visible activity towards other cancer cell lines tested, reflecting that 12a has low cytotoxicity and acts against some types of cancer cells.