2150-43-8

Basic information

• Product Name: Methyl 3,4-dihydroxybenzoate
• Synonyms: METHYL 3,4-DIHYDROXYBENZOATE;METHYL PROTOCATECHUATE;3,4-DIHYDROXY-BENZOIC ACID METHYL ESTER;RARECHEM AL BF 0069;Protocatechuic Acid Methyl Ester;3,4-Dihydroxybenzoic acid methyl;Protocatechuic acid methyl;Methyl 3,4-dihydroxy
• CAS NO: 2150-43-8
• Molecular Formula: C₈H₈O₄
• Molecular Weight: 168.15
• Product Categories: Aromatic Esters;Aromatics, Metabolites & Impurities, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 2150-43-8.mol
• Article Data: 100

Chemical Properties

• Melting Point: 134-135°C
• Boiling Point: 351.5 °C at 760 mmHg
• Flash Point: 148.5 °C
• Appearance: white to off-white crystalline powder
• Density: 1.354 g/cm³
• Vapor Pressure: 2.02E-05mmHg at 25°C
• Refractive Index: 1.587
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 8.19±0.18(Predicted)
• BRN: 1637939
• CAS DataBase Reference: Methyl 3,4-dihydroxybenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 3,4-dihydroxybenzoate(2150-43-8)
• EPA Substance Registry System: Methyl 3,4-dihydroxybenzoate(2150-43-8)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36-37
• Hazardous Substances Data: 2150-43-8(Hazardous Substances Data)

Usage

Description

Methyl 3,4-dihydroxybenzoate, also known as D451680, is a methyl ester derived from the formal condensation of the carboxy group of 3,4-dihydroxybenzoic acid with methanol. It is an off-white solid and possesses antioxidant properties, making it a valuable compound in various applications.

Uses

Used in Pharmaceutical Industry:
Methyl 3,4-dihydroxybenzoate is used as a pharmaceutical compound for its antioxidant properties. It can be utilized in the development of drugs that target oxidative stress-related conditions, as its antioxidant nature can help neutralize harmful free radicals and protect cells from damage.
Used in Cosmetics Industry:
In the cosmetics industry, Methyl 3,4-dihydroxybenzoate is used as an additive for its antioxidant properties. It can be incorporated into skincare products to help protect the skin from environmental stressors, such as pollution and UV radiation, and to maintain the stability of the product formulation.
Used in Food Industry:
Methyl 3,4-dihydroxybenzoate is used as a preservative in the food industry due to its antioxidant properties. It can help extend the shelf life of various food products by preventing oxidation and rancidity, ensuring freshness and maintaining the quality of the product.
Used in Chemical Research:
Methyl 3,4-dihydroxybenzoate is also used as a research compound in the field of chemistry. Its unique structure and properties make it a valuable tool for studying various chemical reactions and processes, contributing to the advancement of scientific knowledge in this area.

InChI:InChI=1/C8H8O4/c1-12-8(11)5-2-3-6(9)7(10)4-5/h2-4,9-10H,1H3

Upstream product

• 67-56-1 methanol 
• 99-50-3 3,4-Dihydroxybenzoic acid 
• 326-56-7 methyl 3,4-methylenedioxybenzoate 
• 3943-74-6 4-hydroxy-3-methoxybenzoic acid methyl ester 
• 81116-73-6 3,4-(Acetoxymethylendioxy)-benzoesaeuremethylester 
• 19438-10-9 methyl 3-hydroxybenzoate 
• 5026-62-0 sodium methylparaben 
• 57764-14-4 methyl 3-dehydroquinate 
• 99-76-3 methyl 4-hydroxylbenzoate 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 168961-20-4 (+)-Methyl 3,4-O-cyclohexylidene-5-didehydroshikimate 
• 7647-01-0 hydrogenchloride 
• 74-88-4 methyl iodide 
• 484018-34-0 methyl 4-(cyclohex-2-en-1-yloxy)-3-hydroxybenzoate 

Downstream Products

• 150191-58-5 methyl 2,5-dichloro-3,4-dihydroxybenzoate 
• 87687-75-0 methyl 4-(benzyloxy)-3-hydroxybenzoate 
• 54544-05-7 3,4-bis-benzyloxybenzoic acid methyl ester 
• 20197-75-5 2,3-dihydro-benzo[1,4]dioxine-6-carboxylic acid methyl ester 
• 645-08-9 Isovanillic acid 
• 144300-83-4 methyl 3,4-bis(7-(2S-methyl-3-acryloyl-4S-tert-butyl-2-oxazolidinyl)heptyloxy)benzoate 
• 144225-91-2 methyl 3,4-bis(7-(2R-methyl-3-acryloyl-4S-tert-butyl-2-oxazolidinyl)heptyloxy)benzoate 
• 134178-06-6 methyl 3,4-bis<(tert-butyldimethylsilyl)oxy>benzoate 
• 137668-94-1 methyl 3,4-bis(tosyloxy)benzoate 

Relevant articles and documents

Study of acylhydrazone derivatives with deoxygenated seven-membered rings as potential β-ketoacyl-acyl carrier protein synthase III (FabH) inhibitors

Fatty acid biosynthesis is essential for bacterial survival. FabH, β-ketoacyl-acyl carrier protein (ACP) synthase III, is a particularly attractive target, since it is central to the initiation of fatty acid biosynthesis and highly conserved among Gram-positive and Gram-negative bacteria. Following previous studies, a series of acylhydrazone derivatives with deoxygenated rings were synthesized in this work. For all of the 36 analogues synthesized, studies using H NMR, C NMR, MS and elemental analyses were conducted. Their biological activities were also evaluated against two Gram-negative bacterial strains: E. coli and P. aeruginosa, and two Gram-positive bacterial strains: B. subtilis and S. aureus by the MTT method as potential FabH inhibitors. The resulting compound F18 showed the highest antibacterial activity with MIC values of 1.56-3.13 μg mL-1 against the tested bacterial strains and was found to be the most potent E. coli FabH inhibitor with an IC50 value of 2.0 μM. Molecular modeling simulation studies were performed in order to predict the biological activities of compound F18 into the E. coli FabH active site.

Oxidative dimers produced from protocatechuic and gallic esters in the DPPH radical scavenging reaction

DPPH (2,2-diphenyl-1-picrylhydrazyl) radical scavenging reactions of protocatechuic and gallic acids, and their methyl esters, have been investigated by NMR. In acetone, methyl protocatechuate was gradually converted to a Diels-Alder adduct of two molecul

Direct conversion of phenols to o-quinones by copper(I) dioxygen. Questions regarding the monophenolase activity of tyrosinase mimics

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Structure-property-activity relationship of phenolic acids and derivatives. Protocatechuic acid alkyl esters

The esterification of hydrophilic phenolic antioxidants is an efficient approach to enhance their solubility in apolar media. Herein, structurea property studies on the antiradical activity of a series of protocatechuic acid alkyl esters have been accomplished. The increase of the lipophilicity was shown to significantly improve the antioxidant activity of protocatechuic esters. Their efficiency as radical scavengers was evaluated using distinctive analytical methods, namely, 2,2-diphenyl-1-picrylhydrazyl (DPPH) UV/visible method, electrochemistry, and differential scanning calorimetry. All the new alkyl protocatechuate antioxidants studied possessed better radical-scavenging capacity than the natural antioxidant protocatechuic acid. This work has shown that the alkyl ester side chain markedly influences the lipophilicity of this type of phenolic system without disturbing the core of the molecule responsible for antioxidant activity. The data on the antioxidant activity obtained using the different analytical methods correlated well with each other and have revealed the interesting antioxidant potential of alkyl esters of protocatechuic acid.

Ethyl acetate as a co-solvent and sacrificial ester in the aluminum triiodide promoted chemoselective demethylation of methyl vanillate

A synthetic approach towards methyl protocatechuate via chemoselective ether cleavage of methyl vanillate without affecting the carboxylate group is disclosed utilizing a ternary reagent system consisting of aluminum triiodide, 1,3-diisopropylcarbodiimide and ethyl acetate. Ethyl acetate serves as a co-solvent and sacrificial ester. Methyl isovanillate, ethyl vanillate and methyl feruate were analogously demethylated to give methyl protocatechuate, ethyl protocatechuate and methyl caffeate, respectively, in fair to excellent yields.

Kinetic Evaluation of Phenolase Activity of Tyrosinase Using Simplified Catalytic Reaction System

A very simple tyrosinase reaction system has been developed using borate anion as a trapping agent of catechols and hydroxylamine as an external reductant to evaluate the phenolase activity without the interference of catecholase activity. Reactivities of variously para-substituted phenols in this system were compared directly to those of the phenols in the model reactions, demonstrating that the enzymatic oxygenation reaction of phenols proceeds via the same mechanism as the model reaction, that is, electrophilic aromatic substitution mechanism. Copyright

Last-Step Enzymatic [18F]-Fluorination of Cysteine-Tethered RGD Peptides Using Modified Barbas Linkers

We report a last-step fluorinase-catalyzed [18F]-fluorination of a cysteine-containing RGD peptide. The peptide was attached through sulfur to a modified and more hydrophilic variant of the recently disclosed Barbas linker which was itself link

Iron-catalyzed arene C-H hydroxylation

The sustainable, undirected, and selective catalytic hydroxylation of arenes remains an ongoing research challenge because of the relative inertness of aryl carbon-hydrogen bonds, the higher reactivity of the phenolic products leading to over-oxidized by-products, and the frequently insufficient regioselectivity. We report that iron coordinated by a bioinspired L-cystine-derived ligand can catalyze undirected arene carbon-hydrogen hydroxylation with hydrogen peroxide as the terminal oxidant. The reaction is distinguished by its broad substrate scope, excellent selectivity, and good yields, and it showcases compatibility with oxidation-sensitive functional groups, such as alcohols, polyphenols, aldehydes, and even a boronic acid. This method is well suited for the synthesis of polyphenols through multiple carbon-hydrogen hydroxylations, as well as the late-stage functionalization of natural products and drug molecules.

Synthesis and application of acrylic resin based on protocatechuic acid

The invention discloses synthesis and application of acrylic resin based on protocatechuic acid. According to the method, protocatechuic acid is used as a raw material, firstly, alcohol is used for esterification, and then the raw material and acryloyl chloride are synthesized into the protocatechuic acid-based acrylic resin monomer (M) through a one-pot method. And the acrylic resin based on protocatechuic acid is used for modifying polymethyl methacrylate (organic glass). The resin monomer is copolymerized with methyl methacrylate (MMA), the glass transition temperature (Tg) is increased along with the increase of the M content, and when the M content is 50%, the Tg of the copolymer is 159.6 DEG C (the heat resistance is improved by 51 DEG C). The Td5 of the copolymer is 358 DEG C (increased by 48 DEG C), and the residual carbon rate is 12.57%. In addition, the copolymerization product also shows the characteristic of absorbing short-wave blue light. The synthesis method provided by the invention is mild in reaction condition and relatively high in yield, and has a relatively great application prospect in the application field of optical electronics. The invention also widens the application range of biological resources.

BENZOXAZINONE COMPOUNDS AS KLK5/7 DUAL INHIBITORS

The present invention provides compounds and pharmaceutical compositions including the compounds for the treatment of a skin disease associated with proteolytic activity of one or more KLK proteases, wherein the compounds are according to formula (I): whe