99-06-9

Usage

Uses

Used in Pharmaceutical Industry:
m-Salicylic acid is used as an intermediate in the synthesis of various pharmaceuticals for its anti-inflammatory and analgesic properties, contributing to the development of medications that alleviate pain and reduce inflammation.
Used in Agrochemical Industry:
m-Salicylic acid serves as an intermediate in the production of agrochemicals, playing a crucial role in the development of compounds that protect crops and enhance agricultural productivity.
Used in Skincare Products:
m-Salicylic acid is used as an active ingredient in skincare products for its acne-treating capabilities, helping to reduce inflammation and unclog pores, thus improving the overall health and appearance of the skin.
Used in Cosmetics and Personal Care Products:
m-Salicylic acid is utilized as a preservative in cosmetics and personal care products, ensuring their stability and preventing microbial contamination, while also providing anti-inflammatory benefits to the skin.
Used in Dye and Fragrance Production:
m-Salicylic acid is employed in the production of dyes and fragrances, contributing to the color and scent characteristics of various consumer products.

InChI:InChI=1/C7H6O3/c8-6-3-1-2-5(4-6)7(9)10/h1-4,8H,(H,9,10)/p-1

Upstream product

• 4518-10-9 Methyl 3-aminobenzoate 
• 94-53-1 Piperonylic acid 
• 620-17-7 3-ethylphenol 
• 610-35-5 4-hydroxyphthalic acid 
• 1743-37-9 diazotierte 3-Amino-benzoesaeure 
• 79-21-0 peracetic acid 
• 64-19-7 acetic acid 
• 100-83-4 meta-hydroxybenzaldehyde 
• 67-56-1 methanol 
• 620-24-6 3-Hydroxybenzyl alcohol 
• 108-43-0 3-monochlorophenol 
• 201230-82-2 carbon monoxide 
• 591-20-8 3-Bromophenol 
• 65-85-0 benzoic acid 

Downstream Products

• 67032-05-7 3-hydroxy-benzoic acid-[3-(2-methyl-piperidino)-propylester]; hydrochloride 
• 6304-89-8 3-acetoxybenzoic acid 
• 28547-22-0 3-(benzoyloxy)benzoic acid 
• 51988-36-4 3-propionyloxy-benzoic acid 
• 19438-10-9 methyl 3-hydroxybenzoate 
• 38567-05-4 Propyl 3-hydroxybenzoate 
• 93351-38-3 3-butoxy-benzoic acid 
• 621-51-2 3-ethoxybenzoic acid 
• 61340-33-8 5-hydroxy-2-((4-nitrophenyl)diazenyl)benzoic acid 
• 53631-77-9 3-hydroxybenzoic acid 1-methylethyl ester 
• 7781-98-8 ethyl-3-hydroxybenzoate 
• 60772-67-0 3-(1-methylethoxy)benzoic acid 
• 52431-73-9 1,3,5-Trihydroxy-anthrachinon 
• 860691-06-1 2-oxo-3-phenyl-2,3-dihydro-benzofuran-4-carboxylic acid 

Relevant academic research and scientific papers

PHOTOCATALYTIC EFFECTS OF Fe(III) COMPOUNDS ON THE HYDROXYLATION OF BENZOIC ACID BY HYDROGEN PEROXIDE INITIATED BY 589 nm RADIATION AND SENSITIZED BY METHYLENE BLUE

The hydroxylation of benzoic acid by hydrogen peroxide initiated by 589 nm radiation is catalyzed by the following Fe(III) compounds: FeCl3, K3, Na2, and K3.This photochemical reaction can be effectively sensitized by methylene blue.

EVIDENCE FOR THE FORMATION OF 1,3- AND 1,4-DEHYDROBENZENES IN THE THERMAL DECOMPOSITION OF DIARYLIODONIUM-CARBOXYLATES

Generation of m- and p-benzynes in decomposition of diaryliodonium- 3- and 4-carboxylates is demonstrated by three-phase method.

Efficiency of lithium cations in hydrolysis reactions of esters in aqueous tetrahydrofuran

Lithium cations were observed to accelerate the hydrolysis of esters with hydroxides (KOH, NaOH, LiOH) in a water/tetrahydrofuran (THF) two-phase system. Yields in the hydrolysis of substituted benzoates and aliphatic esters using the various hydroxides were compared, and the effects of the addition of lithium salt were examined. Moreover, it was presumed that a certain amount of LiOH was dissolved in THF by the coordination of THF with lithium cation and hydrolyzed esters even in the THF layer, as in the reaction by a phase-transfer catalyst.

Cleavage of Carboxylic Esters by Aluminum and Iodine

A one-pot procedure for deprotecting carboxylic esters under nonhydrolytic conditions is described. Typical alkyl carboxylates are readily deblocked to the carboxylic acids by the action of aluminum powder and iodine in anhydrous acetonitrile. Cleavage of lactones affords the corresponding ω-iodoalkylcarboxylic acids. Aryl acetylates undergo deacetylation with the participation of the neighboring group. This method enables the selective cleavage of alkyl carboxylic esters in the presence of aryl esters.

Photocatalytic synthesis of phenols mediated by visible light using KI as catalyst

A transition-metal-free hydroxylation of iodoarenes to afford substituted phenols is described. The reaction is promoted by KI under white LED light irradiation and uses atmospheric oxygen as oxidant. By the use of triethylamine as base and solvent, the corresponding phenols are obtained in moderate to good yields. Mechanistic studies suggest that KI and catalysis synergistically promote the cleavage of C-I bond to form free aryl radicals.

MOF-Zn-NHC as an efficient N-heterocyclic carbene catalyst for aerobic oxidation of aldehydes to their corresponding carboxylic acids: Via a cooperative geminal anomeric based oxidation

As an efficient heterogenous N-heterocyclic carbene (NHC) catalyst, MOF-Zn-NHC was used in the aerobic oxidation of aryl aldehydes to their corresponding carbocyclic acids via an anomeric based oxidation. Features such as mild reaction conditions and no need for a co-catalyst or oxidative reagent can be considered as the major advantages of the presented method in this study. This journal is

Investigation of the requirements for efficient and selective cytochrome P450 monooxygenase catalysis across different reactions

The cytochrome P450 metalloenzyme (CYP) CYP199A4 from Rhodopseudomonas palustris HaA2 catalyzes the highly efficient oxidation of para-substituted benzoic acids. Here we determined crystal structures of CYP199A4, and the binding and turnover parameters, with different meta-substituted benzoic acids in order to establish which criteria are important for efficient catalysis. When compared to the para isomers, the meta-substituted benzoic acids were less efficiently oxidized. For example, 3-formylbenzoic acid was oxidized with lower activity than the equivalent para isomer and 3-methoxybenzoic acid did not undergo O-demethylation by CYP199A4. The structural data highlighted that the meta-substituted benzoic acids bound in the enzyme active site in a modified position with incomplete loss of the distal water ligand of the heme moiety. However, for both sets of isomers the meta- or para-substituent pointed towards, and was in close proximity, to the heme iron. The absence of oxidation activity with 3-methoxybenzoic acid was assigned to the observation that the C[sbnd]H bonds of this molecule point away from the heme iron. In contrast, in the para isomer they are in an ideal location for abstraction. These findings were confirmed by using the bulkier 3-ethoxybenzoic acid as a substrate which removed the water ligand and reoriented the meta-substituent so that the methylene hydrogens pointed towards the heme, enabling more efficient oxidation. Overall we show relatively small changes in substrate structure and position in the active site can have a dramatic effect on the activity.

Copper and L-(?)-quebrachitol catalyzed hydroxylation and amination of aryl halides under air

L-(?)-Quebrachitol, a natural product obtained from waste water of the rubber industry, was utilized as an efficient ligand for the copper-catalyzed hydroxylation and amination of aryl halides to selectively give phenols and aryl amines in water or 95percent ethanol. In addition, the hydroxylation of 2-chloro-4-hydroxybenzoic acid was validated on a 100-g scale under air.

Reductive dehalogenation and dehalogenative sulfonation of phenols and heteroaromatics with sodium sulfite in an aqueous medium

Prototropic tautomerism was used as a tool for the reductive dehalogenation of (hetero)aryl bromides and iodides, or dehalogenative sulfonation of (hetero)aryl chlorides and fluorides, using sodium sulfite as the sole reagent in an aqueous medium. This protocol does not require a metal or phase transfer catalyst and avoids using organic solvent as the reaction medium. This method is especially suitable for substrates that readily tautomerize (such as 2-or 4-halogenated aminophenols and 4-halogenated resorcinols), for which dehalogenation or sulfonation proceeds under mild reaction conditions (≤60 °C). As sodium sulfite is an inexpensive, safe, and environmentally less hazardous reagent, this method has at least three potential applications: (i) in the deprotection of halogens as protecting groups, using sodium sulfite as a reducing agent; (ii) in the sulfonation of aromatic halides under mild reaction conditions avoiding hazardous and corrosive reagents/solvents; and (iii) in the transformation of toxic halogenated aromatics into less harmful compounds.

Exploring the Selective Demethylation of Aryl Methyl Ethers with a Pseudomonas Rieske Monooxygenase

Biocatalytic dealkylation of aryl methyl ethers is an attractive reaction for valorization of lignin components, as well as for deprotection of hydroxy functionalities in synthetic chemistry. We explored the demethylation of various aryl methyl ethers by using an oxidative demethylase from Pseudomonas sp. HR199. The Rieske monooxygenase VanA and its partner electron transfer protein VanB were recombinantly coexpressed in Escherichia coli and they constituted at least 25 % of the total protein content. Enzymatic transformations showed that VanB accepts NADH and NADPH as electron donors. The VanA–VanB system demethylates a number of aromatic substrates, the presence of a carboxylic acid moiety is essential, and the catalysis occurs selectively at the meta position to this carboxylic acid in the aromatic ring. The reaction is inhibited by the by-product formaldehyde. Therefore, we tested three different cascade/tandem reactions for cofactor regeneration and formaldehyde elimination; in particular, conversion was improved by addition of formaldehyde dehydrogenase and formate dehydrogenase. Finally, the biocatalyst was applied for the preparation of protocatechuic acid from vanillic acid, giving a 77 % yield of the desired product. The described reaction may find application in the conversion of lignin components into diverse hydroxyaromatic building blocks and generally offers potential for new, mild methods for efficient unmasking of phenols.