586-30-1

Basic information

• Product Name: 3-Hydroxy-4-methylbenzoic acid
• Synonyms: 4-METHYL-3-HYDROXYBENZOIC ACID;3-HYDROXY-P-TOLUIC ACID;3-HYDROXY-4-METHYLBENZOIC ACID;3,4-CRESOTIC ACID;3-HYDROXY-4-METHYLBENZOIC ACID, TECH.;3-Hydroxy-4-methylbenzoic;3-Hydroxy-4-methylbenzoic acid 95%;3-Hydroxy-p-toluylsure
• CAS NO: 586-30-1
• Molecular Formula: C₈H₈O₃
• Molecular Weight: 152.15
• EINECS: 209-571-2
• Product Categories: FINE Chemical & INTERMEDIATES;Acids and Derivatives;Alcohols and Derivatives;Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Benzoic acid;Organic acids;Acids & Esters;Phenols;Building Blocks;C8;Carbonyl Compounds;Carboxylic Acids;Chemical Synthesis;Organic Building Blocks;alcohol| carboxylic acid
• Mol File: 586-30-1.mol
• Article Data: 5

Chemical Properties

• Melting Point: 205-210 °C(lit.)
• Boiling Point: 234.6°C (rough estimate)
• Flash Point: 181.2 °C
• Appearance: white to slightly beige powder
• Density: 1.2143 (rough estimate)
• Vapor Pressure: 1.41E-05mmHg at 25°C
• Refractive Index: 1.4447 (estimate)
• Storage Temp.: Store below +30°C.
• PKA: 4.25±0.10(Predicted)
• Water Solubility: 43.5g/L(100 oC)
• BRN: 1936497
• CAS DataBase Reference: 3-Hydroxy-4-methylbenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Hydroxy-4-methylbenzoic acid(586-30-1)
• EPA Substance Registry System: 3-Hydroxy-4-methylbenzoic acid(586-30-1)

Safety Data

• Hazard Codes: Xi,C
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 1
• HazardClass: IRRITANT
• Hazardous Substances Data: 586-30-1(Hazardous Substances Data)

Usage

Chemical Properties

white to slightly beige powder

Uses

Methyl Hydroxybenzoic Acid is also used in the preparation of a potent tie-2 kinase inhibitor in the inhibition of angiogenesis and tumor suppression. Used in the preparation of inhibitors of phosphatine kinases.

InChI:InChI=1/C8H8O3/c1-5-2-3-6(8(10)11)4-7(5)9/h2-4,9H,1H3,(H,10,11)

Upstream product

• 5162-82-3 3-chloro-4-methylbenzoic acid 
• 7697-26-9 3-bromo-4-methylbenzoic acid 
• 7151-68-0 3-methoxy-p-toluic acid 
• 90113-39-6 3-hydroxy-4-methyl-cyclohexanecarboxylic acid 
• 3816-66-8 3-hydroxy-4-methylbenzonitrile 
• 62454-72-2 4-methyl-3-sulfobenzoic acid 
• 7726-95-6 bromine 
• 939-79-7 4-cyano-2-nitrotoluene 
• 60710-80-7 5-cyano-2-methylaniline 
• 99-94-5 p-Toluic acid 
• 36138-76-8 5-bromo-2-methylphenol 
• 67868-73-9 5-bromo-2-methylphenol methyl ether 
• 3695-37-2 2-mercapto-p-cymene 
• 76-22-2 Camphor 

Downstream Products

• 857543-59-0 7-methyl-2-oxo-3-phenyl-2,3-dihydro-benzofuran-4-carboxylic acid 
• 4342-60-3 4-methylcyclohex-3-enecarboxylic acid 
• 90953-62-1 3-hydroxy-4-methylbenzyl alcohol 
• 95-48-7 ortho-cresol 
• 17477-46-2 3-acetyloxy-4-methylbenzoic acid 
• 3556-83-0 methyl 4-methyl-3-methoxybenzoate 
• 7151-68-0 3-methoxy-p-toluic acid 
• 90113-39-6 3t-hydroxy-4ξ-methyl-cyclohexane-r-carboxylic acid 
• 90113-39-6 (+/-)-3c-hydroxy-4t-methyl-cyclohexane-carboxylic acid-(1r) 
• 3556-86-3 methyl 4-methyl-3-hydroxybenzoate 
• 926277-91-0 4-methyl-3-(3-(pyrimidin-4-yl)pyridin-2-yloxy)benzoic acid 
• 926277-89-6 4-methyl-3-(3-(2-(methylamino)pyrimidin-4-yl)pyridin-2-yloxy)benzoic acid 
• 926277-90-9 N-(5-cyclohexyl-2-methoxyphenyl)-3-hydroxy-4-methylbenzamide 

Relevant articles and documents

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.

Process for the synthesis of biologically active oxygenated compounds by dealkylation of the corresponding alkylethers

Alkoxy aromatic compounds are conveniently dealkylated to the corresponding phenolic compounds by treatment with aluminum chloride/N,N-dimethyl aniline complex. Aromatic poly O-demethylation is a unique feature of this invention. This process is applicable to the manufacture of polyphenols such as Resveratrol, Oxyresveratrol, Gnetol.

Baker's yeast-mediated enantioselective synthesis of the bisabolane sesquiterpenes (+)-curcuphenol, (+)-xanthorrhizol, (-)-curcuquinone and (+)-curcuhydroquinone

Fermenting baker's yeast converts the unsaturated aldehydes 5a-c into the saturated alcohols 6a-c, respectively. The microbial saturation of substrates adsorbed on a nonpolar resin proceeds in high chemical yields and shows complete enantioselectivity in the formation of the (S)-(+) isomers. Enantiopure 6a-c are versatile chiral building blocks for the synthesis of bisabolane sesquiterpenes. Their usefulness is shown in the preparation of (S)-(+)-curcuphenol, (S)-(+)-xanthorrhizol, (S)-(-)-curcuquinone and (S)-(+)-curcuhydroquinone. The Royal Society of Chemistry 2000.