2107-70-2

Basic information

• Product Name: 3,4-Dimethoxyhydrocinnamic acid
• Synonyms: 3-(3,4-DiMethoxyphenyl)propionic acid, 99% 50GR;3-(3,4-DiMethoxy)phenyl Proponoic Acid;3,4-DiMethoxy-benzenepropanoic acid;3-(3,4-Dimethoxyphenyl)propanonic acid 99%;3,4-Dimethoxyhydrocinnamic acid, 3-(3,4-Dimethoxyphenyl)propionic acid;3-(3,4- twoMethoxy phenyl)propionic acid;3-(3,4-DiMethoxyphenyl)propionic Acid, 97+%;DiMethoxyphenyl)propionic ac
• CAS NO: 2107-70-2
• Molecular Formula: C₁₁H₁₄O₄
• Molecular Weight: 210.23
• EINECS: 218-288-3
• Product Categories: intermediate;Aromatics, Metabolites & Impurities;Aromatic Propionic Acids;Cinnamic acid;Organic acids;Aromatics
• Mol File: 2107-70-2.mol

Chemical Properties

• Melting Point: 96-97 °C(lit.)
• Boiling Point: 309.75°C (rough estimate)
• Flash Point: 132.022 °C
• Appearance: Slightly beige/Crystalline Powder
• Density: 1.1922 (rough estimate)
• Vapor Pressure: 2.56E-05mmHg at 25°C
• Refractive Index: 1.5384 (estimate)
• Storage Temp.: -20°C Freezer
• Solubility: DMSO, Water
• PKA: 4.71±0.10(Predicted)
• BRN: 2696272
• CAS DataBase Reference: 3,4-Dimethoxyhydrocinnamic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-Dimethoxyhydrocinnamic acid(2107-70-2)
• EPA Substance Registry System: 3,4-Dimethoxyhydrocinnamic acid(2107-70-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 2107-70-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3,4-Dimethoxyhydrocinnamic acid is used as a pharmaceutical compound for its potential role in inducing γ globin gene expression in reporter assays and erythropoiesis in vivo. This application is significant in the development of treatments for various blood-related disorders and conditions.
Used in Coffee Metabolism Research:
As a novel circulating coffee metabolite in human plasma, 3,4-Dimethoxyhydrocinnamic acid is used in the study of coffee's effects on human health and metabolism. This research can contribute to a better understanding of the benefits and potential risks associated with coffee consumption.
Used in Chemical and Material Science:
The complex formation between 3,4-Dimethoxyhydrocinnamic acid and copper (II) makes it a valuable compound in the field of chemical and material science. This property can be exploited for various applications, such as in the development of new materials with specific properties or in the synthesis of other complex molecules.

InChI:InChI=1/C11H14O4/c1-14-9-5-3-8(4-6-11(12)13)7-10(9)15-2/h3,5,7H,4,6H2,1-2H3,(H,12,13)/p-1

Upstream product

• 6380-23-0 3,4-dimethoxystyrene 
• 590-29-4 potassium formate 
• 5460-32-2 1-iodo-3,4-dimethoxybenzene 
• 802294-64-0 propionic acid 
• 118199-01-2 2,2-dibromo-1-(3,4-dimethoxyphenyl)ethene 
• 71616-34-7 ethyl 3-(3',4'-dimethoxyphenyl)propiolate 
• 1135-24-6 (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid 
• 5462-13-5 ethyl 3-(3,4-dimethoxyphenyl)propionate 
• 67101-91-1 5-[(3,4-dimethoxyphenyl)methylene]-2,2-dimethyl-1,3-dioxane-4,6-dione 
• 154317-78-9 5-(3,4-dimethoxybenzyl)-2,2-dimethyl-[1,3]dioxane-4,6-dione 
• 1658-27-1 1,5-dioxaspiro[5.5]undecane-2,4-dione 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 154318-00-0 2-(4-fluorophenyl)-1,3-dioxane-4,6-dione 
• 3709-16-8 2-phenyl-1,3-dioxane-4,6-dione 

Downstream Products

• 102375-29-1 3-(3,4-dimethoxy-phenyl)-propionic acid-(2-indol-3-yl-ethylamide) 
• 35491-94-2 1-chloro-4-(3,4-dimethoxy-phenyl)-butan-2-one 
• 5467-91-4 1,3-bis[2-(3,4-dimethoxyphenyl)ethyl]urea 
• 25017-47-4 N-<2-(3,4-dimethoxyphenylethyl)>urea 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 13575-74-1 4-(3,4-dimethoxyphenyl)butanoic acid 
• 3916-70-9 1,2-dimethoxy-4-(3-nitropropyl)benzene 
• 4503-15-5 1-<3.4-Dimethoxy-phenyl>-propanol-(3)-<3.5-dinitro-benzoat> 
• 3912-65-0 (+/-)-Acanthoidin 
• 3945-85-5 1-bromo-3-(3,4-dimethoxyphenyl)propane 
• 3912-66-1 (+/-)-1,4-Diamino-6-(3,4-dimethoxy-phenyl)-hexan 
• 3929-48-4 (+/-)-6-(3,4-Dimethoxy-phenyl)-4-nitro-hexansaeure-amid 
• 92498-35-6 (+/-)-6-(3,4-Dimethoxy-phenyl)-4-nitro-hexansaeure-methylester 
• 13575-75-2 6,7-dimethoxy-1-oxo-1,2,3,4-tetrahydronaphthalene 

Relevant articles and documents

A porous, crystalline truxene-based covalent organic framework and its application in humidity sensing

Truxene is employed as a building block to successfully synthesize novel covalent organic frameworks (COFs). The condensation reaction between truxene (10,15-dihydro-5H-diindeno[1,2-a:1′,2′-c]fluorene, TX) and 1,4-phenylenediboronic acid (DBA) results in a crystalline COF with boron ester linkages (COF-TXDBA) and a surface area of 1526 m2 g-1, as confirmed by powder X-ray diffraction (PXRD) and Brunauer-Emmett-Teller (BET) surface area measurements. This is the first study where nanochannels generated by periodic COF planar layers are shown to ease the interactions of the boron ester linkages with the water molecules for efficient humidity sensing. The COF-TXDBA based % RH sensor exhibits a change of 3 orders of magnitude in impedance in the 11-98% RH range, with response and recovery times of 37 s and 42 s, respectively. The response transients measured by switching COF-TXDBA sensor back and forth in 4 loops of % RH range displays excellent reversibility of the sensor with a deviation of 2.3% in the switching process.

Photoinduced Hydrocarboxylation via Thiol-Catalyzed Delivery of Formate across Activated Alkenes

Herein we disclose a new photochemical process to prepare carboxylic acids from formate salts and alkenes. This redox-neutral hydrocarboxylation proceeds in high yields across diverse functionalized alkene substrates with excellent regioselectivity. This operationally simple procedure can be readily scaled in batch at low photocatalyst loading (0.01% photocatalyst). Furthermore, this new reaction can leverage commercially available formate carbon isotologues to enable the direct synthesis of isotopically labeled carboxylic acids. Mechanistic studies support the working model involving a thiol-catalyzed radical chain process wherein the atoms from formate are delivered across the alkene substrate via CO2?- as a key reactive intermediate.

Generalized Chemoselective Transfer Hydrogenation/Hydrodeuteration

A generalized, simple and efficient transfer hydrogenation of unsaturated bonds has been developed using HBPin and various proton reagents as hydrogen sources. The substrates, including alkenes, alkynes, aromatic heterocycles, aldehydes, ketones, imines, azo, nitro, epoxy and nitrile compounds, are all applied to this catalytic system. Various groups, which cannot survive under the Pd/C/H2 combination, are tolerated. The activity of the reactants was studied and the trends are as follows: styrene'diphenylmethanimine'benzaldehyde'azobenzene'nitrobenzene'quinoline'acetophenone'benzonitrile. Substrates bearing two or more different unsaturated bonds were also investigated and transfer hydrogenation occurred with excellent chemoselectivity. Nano-palladium catalyst in situ generated from Pd(OAc)2 and HBPin extremely improved the TH efficiency. Furthermore, chemoselective anti-Markovnikov hydrodeuteration of terminal aromatic olefins was achieved using D2O and HBPin via in situ HD generation and discrimination. (Figure presented.).

Discovery of an Orally Bioavailable and Central Nervous System (CNS) Penetrant mGlu7 Negative Allosteric Modulator (NAM) in Vivo Tool Compound: N-(2-(1 H-1,2,4-triazol-1-yl)-5-(trifluoromethoxy)phenyl)-4-(cyclopropylmethoxy)-3-methoxybenzamide (VU6012962)

Herein, we report the discovery of a new, orally bioavailable and CNS-penetrant metabotropic glutamate receptor 7 (mGlu7) negative allosteric modulator (NAM) that achieves exposure in cerebral spinal fluid (CSF) 2.5× above the in vitro IC50 at minimum effective doses (MEDs) of 3 mg/kg in preclinical anxiety models.

Substituted cinnamic anhydrides act as selective inhibitors of acetylcholinesterase

Cinnamic anhydrides have been shown to be more than reactive reagents, but they also act as inhibitors of the enzyme acetylcholinesterease (AChE). Thus, out of a set of 33 synthesised derivatives, several of them were mixed type inhibitors for AChE (from electric eel). Thus, (E)-3-(2,4-dimethoxyphenyl)acrylic anhydride (2c) showed Ki = 8.30 ± 0.94 μM and Ki′ = 9.54 ± 0.38 μM, and for (E)-3-(3-chlorophenyl)acrylic anhydride (2u) Ki = 8.23 ± 0.93 μM and Ki′ = 13.07 ± 0.46 μM were measured. While being not cytotoxic to many human cell lines, these compounds showed an unprecedented and noteworthy inhibitory effect for AChE but not for butyrylcholinesterase (BChE).

Synthesis of various arylated trifluoromethyl substituted indanes and indenes, and study of their biological activity

A series of 1-trifluoromethyl substituted indanes and indenes bearing aryl groups in positions 1 and/or 3 of the indane core have been synthesized mainly by electrophilic cyclization and arylation of the corresponding trifluoromethylated allyl and propargyl alcohols. The distinctly lipophilic compounds thus obtained were tested against various components of human endocannabinoid system. None of the compounds displayed affinity toward CB1 or CB2 receptors. Two compounds inhibited monoacylglycerol lipase (MAGL) and three compounds showed inhibition of anandamide (AEA) uptake. The latter can be related to the low-micromolar inhibition of fatty acid amide hydrolase (FAAH) inhibition displayed by one of these compounds.

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.

Synthesis, in vitro and in silico evaluation of diaryl heptanones as potential 5LOX enzyme inhibitors

A new series of diaryl heptanones (12a-q) were synthesized and their structures were confirmed by its 1H, 13C NMR and Mass spectral data. These analogs were evaluated for their anti-oxidant activity and potential to inhibit 5-lipoxygenase. Compounds 12k and 12o showed potent in vitro 5-lipoxygenase enzyme inhibitory activity with IC50 values of 22.2, 21.5 μM, which are comparable to curcumin (24.4 μM). Further they also have shown significant antioxidant activity. Molecular docking studies clearly showed correlation between binding energy and potency of these compounds.

Pd-Catalyzed β-C(sp3)?H Arylation of Propionic Acid and Related Aliphatic Acids

A generally applicable Pd-catalyzed protocol for the β-C(sp3)?H arylation of propionic acid and related α-branched aliphatic acids is reported. Enabled by the use of N-acetyl-β-alanine as ligand our protocol delivers a broad range of arylation products. Notably, the highly challenging substrate, propionic acid, which lacks any acceleration through the Thorpe–Ingold effect, can be employed as substrate with synthetically useful yields. Furthermore, the scalability and synthetic applicability of the protocol are demonstrated.

A 3,4-dimethoxy-method for preparation of propionic acid (by machine translation)

The invention belongs to the technical field of chemical synthesis, in particular relates to a key intermediate donepezil hydrochloride 3,4-dimethoxy-method for preparation of propionic acid. The method comprises the following steps: to 3,4-dimethoxy-benzaldehyde as a raw material, sodium in ethanol and ethyl acetate under the action of the reaction, the intermediate 3,4-di-methoxy cinnamic acid ethyl ester; 3,4-di-methoxy cinnamic acid ethyl ester hydrolysis under alkaline conditions after the, re-hydrogenation reduction to obtain 3,4-dimethoxy-propionic acid. The preparation method of this invention has is friendly to the environment, the product has high purity, high yield, low cost of raw materials, and the like. (by machine translation)