93-07-2

Basic information

• Product Name: 3,4-Dimethoxybenzoic acid
• Synonyms: (2R)-2,7,8-Trimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]chroman-6-ol;3,4-DiMethoxybenzoic acid, 99+% 100GR;NSC 7721;Protocatechuic Acid Dimethyl Ether Veratric Acid;3,4-DIMETHOXYBENZOIC ACID FOR SYNTHESIS;DiMethoxybenzoic aci;3,4- twoMethoxybenzoic acid;3,4-Dimethoxybenzoic acid≥ 99% (Titration)
• CAS NO: 93-07-2
• Molecular Formula: C₉H₁₀O₄
• Molecular Weight: 182.17
• EINECS: 202-215-7
• Product Categories: Organic acids;Aromatics;Miscellaneous Reagents;Building Blocks;C9;Carbonyl Compounds;Carboxylic Acids;Chemical Synthesis;Organic Building Blocks;intermediate;Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;BenzoicAcidDerivative
• Mol File: 93-07-2.mol
• Article Data: 193

Chemical Properties

• Melting Point: 179-182 °C(lit.)
• Boiling Point: 275.56°C (rough estimate)
• Flash Point: 120.921 °C
• Appearance: Almost white to beige or reddish/Crystalline Powder
• Density: 1.2481 (rough estimate)
• Vapor Pressure: 0.000423mmHg at 25°C
• Refractive Index: 1.4500 (estimate)
• Storage Temp.: Refrigerator
• Solubility: 0.5g/l
• PKA: 4.35±0.10(Predicted)
• Water Solubility: slightly soluble
• Stability: Stable. Incompatible with strong oxidizing agents.
• Merck: 14,9953
• BRN: 518285
• CAS DataBase Reference: 3,4-Dimethoxybenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-Dimethoxybenzoic acid(93-07-2)
• EPA Substance Registry System: 3,4-Dimethoxybenzoic acid(93-07-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• RTECS: DG8598750
• TSCA: Yes
• Hazardous Substances Data: 93-07-2(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 93-07-2 differently. You can refer to the following data:
1. Derivative of Protocatechuic Acid, and is a reagent used in the production of antimicrobial agents, antifeedants, and a variety of other biologically active compounds.
2. 3,4-Dimethoxybenzoic acid is a derivative of Protocatechuic Acid.3,4-Dimethoxybenzoic acid is a reagent used in the production of antimicrobial agents, antifeedants, and a variety of other biologically active compounds.
3. 3,4-Dimethoxybenzoic acid plays an important role in producing antibiotics and various dyes. They are used as intermediates for pharmaceuticals (especially for antipyretic analgesic, antirheumatism) and other organic synthesis. It is used as matrix for ionization of peptides, proteins and carbohydrates.

Definition

ChEBI: A member of the class of benzoic acids that is benzoic acid substituted by methoxy groups at positions 2 and 3.

Synthesis Reference(s)

Chemical and Pharmaceutical Bulletin, 26, p. 299, 1978 DOI: 10.1248/cpb.26.299Tetrahedron Letters, 43, p. 4985, 2002 DOI: 10.1016/S0040-4039(02)00929-2

Purification Methods

Crystallise the acid from Et2O, H2O or aqueous acetic acid. It has m 180-181o after sublimation at 80o/1mm. [Beilstein 10 H 393, 10 I 188, 10 II 261, 10 III 1404, 10 IV 1406.]

InChI:InChI=1/C9H10O4/c1-12-7-4-3-6(9(10)11)5-8(7)13-2/h3-5H,1-2H3,(H,10,11)/p-1

Upstream product

• 1117-96-0 Diazoethan 
• 60-29-7 diethyl ether 
• 64-17-5 ethanol 
• 85-65-4 pseudolaudanine 
• 2024-83-1 veratronitrile 
• 1521-41-1 veratramide 
• 860763-59-3 3-benzo[1,3]dioxol-5-yl-1-(3,4-dimethoxy-phenyl)-propan-1-one 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 71-43-2 benzene 
• 99-50-3 3,4-Dihydroxybenzoic acid 
• 77-78-1 dimethyl sulfate 
• 93-16-3 Methylisoeugenol 
• 51-43-4 L-epinephrine 
• 124-41-4 sodium methylate 

Downstream Products

• 1521-41-1 veratramide 
• 35296-44-7 1-(3,4-dimethoxy-phenyl)-9H-pyrano[3,4-b]indol-3-one 
• 102011-15-4 N-<2-(3,4-dimethoxyphenyl)ethyl>-3,4-dimethoxyphenylacetamide 
• 192988-59-3 2-(3,4-dimethoxyphenyl)-4,5-dihydro-1H-imidazole 
• 4131-03-7 bis(3,4-dimethoxyphenyl)methanone 
• 6286-46-0 2-bromo-4,5-dimethoxybenzoic acid 
• 709-09-1 3,4-dimethoxynitrobenzene 
• 4998-07-6 4,5-dimethoxy-2-nitro-benzoic acid 
• 645-08-9 Isovanillic acid 
• 121-34-6 3-methoxy-4-hydroxybenzoic acid 
• 3395-03-7 4,5-dimethoxy-1,2-dinitrobenzene 
• 61203-48-3 2-iodo-4,5-dimethoxybenzoic acid 
• 953387-94-5 3,4-dimethoxyphenyl 3,4-dimethoxybenzoate 
• 127462-89-9 (2S)-N-(3,4-dimethoxybenzoyl)proline 

Relevant articles and documents

ON THE KNOWLEDGE OF VIETNAMESE CITRONELLA OIL.

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Enzymatic oxidation of manganese ions catalysed by laccase

The principal possibility of enzymatic oxidation of manganese ions by fungal Trametes hirsuta laccase in the presence of oxalate and tartrate ions, whereas not for plant Rhus vernicifera laccase, was demonstrated. Detailed kinetic studies of the oxidation of different enzyme substrates along with oxygen reduction by the enzymes show that in air-saturated solutions the rate of oxygen reduction by the T2/T3 cluster of laccases is fast enough not to be a readily noticeable contribution to the overall turnover rate. Indeed, the limiting step of the oxidation of high-redox potential compounds, such as chelated manganese ions, is the electron transfer from the electron donor to the T1 site of the fungal laccase.

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The structure of akiferinin

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Kinetics and process parameter studies in catalytic air oxidation of veratraldehyde to veratric acid

Kinetics and different process parameters for the air oxidation of veratraldehyde to veratric acid were studied. At a temperature of 130 °C, air pressure of 1 MPa, cobalt acetate loading of 0.03 mol/L, and an initial concentration of 30% w/v of veratraldehyde, the reaction was found to be first order with respect to veratraldehyde. In 3 h at an aldehyde conversion level of 100%, as high as 99% selectivity was achieved.

Ruthenium-on-Carbon-Catalyzed Facile Solvent-Free Oxidation of Alcohols: Efficient Progress under Solid-Solid (Liquid)-Gas Conditions

A protocol for the ruthenium-on-carbon (Ru/C)-catalyzed solvent-free oxidation of alcohols, which proceeds efficiently under solid-solid (liquid)-gas conditions, was developed. Various primary and secondary alcohols were transformed to corresponding aldehydes and ketones in moderate to excellent isolated yields by simply stirring in the presence of 10% Ru/C under air or oxygen conditions. The solvent-free oxidation reactions proceeded efficiently regardless of the solid or liquid state of the substrates and reagents and could be applied to gram-scale synthesis without loss of the reaction efficiency. Furthermore, the catalytic activity of Ru/C was maintained after five reuse cycles.

Polyhydroxybenzoic acid derivatives as potential new antimalarial agents

With more than 200 million cases and 400,000 related deaths, malaria remains one of the deadliest infectious diseases of 2021. Unfortunately, despite the availability of efficient treatments, we have observed an increase in people infected with malaria since 2015 (from 211 million in 2015 to 229 million in 2019). This trend could partially be due to the development of resistance to all the current drugs. Therefore, there is an urgent need for new alternatives. We have, thus, selected common natural scaffolds, polyhydroxybenzoic acids, and synthesized a library of derivatives to better understand the structure–activity relationships explaining their antiplasmodial effect. Only gallic acid derivatives showed a noticeable potential for further developments. Indeed, they showed a selective inhibitory effect on Plasmodium (IC50 ~20 μM, SI > 5) often associated with interesting water solubility. Moreover, this has confirmed the critical importance of free phenolic functions (pyrogallol moiety) for the antimalarial effect. Methyl 4-benzoxy-3,5-dihydroxybenzoate (39) has, for the first time, been recognized as a potential lead for future research because of its marked inhibitory activity against Plasmodium falciparum and its significant hydrosolubility (3.72 mM).