50-85-1

Basic information

• Product Name: 4-Methylsalicylic acid
• Synonyms: 2,4-cresoticacid;2-hydroxy-4-methyl-benzoicaci;4-Methyl-2-hydroxybenzoic acid;Benzoic acid, 2-hydroxy-4-methyl-;gamma-Cresotic acid;gamma-cresoticacid;m-Homosalicylic acid;m-homosalicylicacid
• CAS NO: 50-85-1
• Molecular Formula: C₈H₈O₃
• Molecular Weight: 152.15
• EINECS: 200-068-3
• Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Aromatics
• Mol File: 50-85-1.mol

Chemical Properties

• Melting Point: 173-177 °C(lit.)
• Boiling Point: 234.6°C (rough estimate)
• Flash Point: 158.6 °C
• Appearance: White to grayish-beige/Powder
• Density: 1.2143 (rough estimate)
• Vapor Pressure: 0.000188mmHg at 25°C
• Refractive Index: 1.4945 (estimate)
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: Chloroform (Slightly, Sonicated), DMSO (Slightly), Methanol (Slightly)
• PKA: pK1:3.17 (25°C)
• Water Solubility: Soluble in water 10 g/L @ 20℃.
• Merck: 14,2580
• BRN: 2208140
• CAS DataBase Reference: 4-Methylsalicylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Methylsalicylic acid(50-85-1)
• EPA Substance Registry System: 4-Methylsalicylic acid(50-85-1)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• RTECS: GP3920100
• Hazardous Substances Data: 50-85-1(Hazardous Substances Data)

Usage

Uses

Used in Chemical Industry:
4-Methylsalicylic acid is used as an intermediate in the manufacturing of dyes. Its structural similarity to salicylic acid allows it to be a valuable component in the synthesis of various dye compounds, contributing to the color and stability of the final product.
Used in Pharmaceutical Industry:
4-Methylsalicylic acid has been identified for its potential use in inhibiting the enzyme medium chain acyl-CoA synthetase. This enzyme plays a crucial role in the metabolism of fatty acids, and its inhibition can have therapeutic implications in the treatment of certain metabolic disorders and diseases.

Purification Methods

Crystallise the acid from water. It sublimes at 130o/11mm. [Beilstein 10 H 233, 10 II 137, 10 III 521, 10 IV 617.]

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

Upstream product

• 95-87-4 2,5-Dimethylphenol 
• 41796-13-8 2,7-dimethyl-4H-chromen-4-one 
• 14002-90-5 4,7-dimethyl-coumarin 
• 19814-69-8 3,6-dimethylxanthen-9-one 
• 698-27-1 4-methylsalicylaldehyde 
• 57415-35-7 2-methoxy-4-methylbenzaldehyde 
• 60770-00-5 ethyl 4-methylsalicylate 
• 5331-40-8 1-(2-hydroxy-4-methyl-phenacyl)-pyridinium; iodide 
• 6921-64-8 4'-hydroxy-2'-methylacetophenone 
• 127-09-3 sodium acetate 
• 108-24-7 acetic anhydride 
• 56-23-5 tetrachloromethane 
• 108-39-4 3-methyl-phenol 
• 2305-36-4 4-methylanthranilic acid 

Downstream Products

• 4670-56-8 methyl 2-hydroxy-4-methylbenzoate 
• 6623-35-4 5-bromo-2-hydroxy-4-methylbenzoic acid 
• 40547-32-8 1,3-dihydroxy-6-methyl-9H-xanthen-9-one 
• 861619-12-7 2-hydroxy-4-methyl-6-(2,2,2-trichloro-1-hydroxy-ethyl)-benzoic acid 
• 876473-62-0 2-hydroxy-4-methyl-5-(2,2,2-trichloro-1-hydroxy-ethyl)-benzoic acid 
• 859178-20-4 2-hydroxy-4-methyl-5-(1,2,2,2-tetrachloro-ethyl)-benzoic acid 
• 60770-00-5 ethyl 4-methylsalicylate 
• 700-38-9 2-nitro-5-methylphenol 
• 602-99-3 3-methyl-2,4,6-trinitrophenol 
• 698-27-1 4-methylsalicylaldehyde 

Relevant articles and documents

Synthesis of cresotic acids by carboxylation of cresols with sodium ethyl carbonate

Carboxylation of o-cresol, m-cresol, and p-cresol with sodium ethyl carbonate (SEC) proceeds regioselectively with the formation of cresotic acids: 2-hydroxy-3-methylbenzoic acid, 2-hydroxy-4-methylbenzoic acid, and 2-hydroxy-5-methylbenzoic acid, respectively. Optimal conditions for conducting the process have been found to be as follows: the reactants ratio of [cresol]: [sodium ethyl carbonate] = (1.5–2): 1, T = 180–185°C, PCO2 = 10 atm, and t = 6–7 h. Simple and convenient methods for the synthesis of cresotic acids, which can be used for their industrial manufacturing, have been developed.

Palladium-catalyzed ortho-C-H hydroxylation of benzoic acids

A simple Pd(OAc)2 catalyzed ortho-hydroxylation of benzoic acids using TBHP as the sole oxidant has been explored. This protocol features relatively broad substrate scope and operational simplicity. The compatibility of ortho-substituted substrates is an effective complement to the previous ortho-hydroxylation reaction.

Carboxylation of Phenols with CO2 at Atmospheric Pressure

A convenient and efficient method for the ortho-carboxylation of phenols under atmospheric CO2 pressure has been developed. This method provides an alternative to the previously reported Kolbe-Schmitt method, which requires very high pressures of CO2. The addition of a trisubstituted phenol has proved essential for the successful carboxylation of phenols with CO2 at standard atmospheric pressure, allowing the efficient preparation of a broad variety of salicylic acids.

General method for the synthesis of salicylic acids from phenols through palladium-catalyzed silanol-directed C-H carboxylation

A silanol-directed, palladium-catalyzed C-H carboxylation reaction of phenols to give salicylic acids has been developed. This method features high efficiency and selectivity, and excellent functional-group tolerance. The generality of this method was demonstrated by the carboxylation of estrone and by the synthesis of an unsymmetrically o,o′-disubstituted phenolic compound through two sequential C-H functionalization processes.

Regioselective ortho-carboxylation of phenols catalyzed by benzoic acid decarboxylases: A biocatalytic equivalent to the Kolbe-Schmitt reaction

The enzyme catalyzed carboxylation of electron-rich phenol derivatives employing recombinant benzoic acid decarboxylases at the expense of bicarbonate as CO2 source is reported. In contrast to the classic Kolbe-Schmitt reaction, the biocatalytic equivalent proceeded in a highly regioselective fashion exclusively at the ortho-position of the phenolic directing group in up to 80% conversion. Several enzymes were identified, which displayed a remarkably broad substrate scope encompassing alkyl, alkoxy, halo and amino- functionalities. Based on the crystal structure and molecular docking simulations, a mechanistic proposal for 2,6-dihydroxybenzoic acid decarboxylase is presented.

PD(II)-CATALYZED HYDROXYLATION OF ARENES WITH O2 OR AIR

Pd (II) -catalyzed ortho-hydroxylat ion of variously substituted aromatic carboxylic acids under O2 or air is achieved under non-acidic conditions. Extensive labeling studies support a direct oxygenation of aryl C-H bonds with molecular oxygen.

Pd(II)-catalyzed hydroxylation of arenes with 1 atm of O2 or air

(Chemical Equation Presented) Pd(II)-catalyzed ortho-hydroxylation of variously substituted benzoic acids under 1 atm of O2 or air is achieved under nonacidic conditions. Extensive labeling studies support a direct oxygenation of aryl C-H bonds with molecular oxygen.

Process for the synthesis of hydroxy aromatic acids

Hydroxy aromatic acids are produced in high yields and high purity (>95%) from halogenated aromatic acids in a reaction mixture containing a copper source and a ligand that coordinates to copper.

COMPOSITIONS AND METHODS FOR THE TREATMENT OF IMMUNOMEDIATED INFLAMMATORY DISORDERS

Compositions and methods for the prevention and treatment of immunomediated inflammatory disorders, especially for those disorders associated with the respiratory tract, are provided. More particularly, a tryptase inhibitor, typically a hydroxyaroyl or hydroxyheteroaroyl substituted dipeptide, is administered. Also provided by this invention are pharmaceutical compositions, typically aerosol or topical, as well as aerosol devices for administering these compositions intranasally.

External preparation for skin

An external preparing for skin comprising one or more than two types of 2-hydroxy benzoic acid derivative and/or salt thereof represented by the following formula: STR1 wherein R is an alkoxy group or alkyl group in the formula. The external preparation for the skin according to the present invention has a suppression effect on melanine generation by inhibition of tyrosinase activity. Accordingly, an excellent bleaching effect based upon the suppression of chromatosis and a high degree of safety can be obtained.