42013-20-7

Basic information

• Product Name: 2-METHYLHIPPURIC ACID
• Synonyms: N-(O-TOLUOYL)GLYCINE;O-METHYLHIPPURIC ACID;O-TOLURIC ACID;N-(2-METHYL-BENZOYL)GLYCINE;[(2-METHYLBENZOYL)AMINO]ACETIC ACID;2-METHYLHIPPURIC ACID;ORTHO-METHYLHIPPURICACID;O-METHYLHIPPURIC ACID STANDARD
• CAS NO: 42013-20-7
• Molecular Formula: C₁₀H₁₁NO₃
• Molecular Weight: 193.2
• EINECS: 255-622-7
• Product Categories: Aromatics;Metabolites & Impurities
• Mol File: 42013-20-7.mol
• Article Data: 7

Chemical Properties

• Melting Point: 161-164 °C(lit.)
• Boiling Point: 329.41°C (rough estimate)
• Flash Point: 207.3 °C
• Appearance: white crystalline powder
• Density: 1.2307 (rough estimate)
• Vapor Pressure: 8.89E-08mmHg at 25°C
• Refractive Index: 1.5300 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 3.71±0.10(Predicted)
• CAS DataBase Reference: 2-METHYLHIPPURIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2-METHYLHIPPURIC ACID(42013-20-7)
• EPA Substance Registry System: 2-METHYLHIPPURIC ACID(42013-20-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26
• WGK Germany: 3
• Hazardous Substances Data: 42013-20-7(Hazardous Substances Data)

Usage

Chemical Properties

WHITE CRYSTALLINE POWDER

Uses

The main metabolite of o-xylene.

Definition

ChEBI: An N-acylglycine that is the ortho-methyl derivative of hippuric acid.

General Description

2-Methylhippuric acid is also known as o-methylhippuric acid and its determination in urine by gas chromatography was reported. It is the urinary metabolic biomarker for the diagnosis of human Hepatitis B virus.

InChI:InChI=1/C10H11NO3/c1-7-4-2-3-5-8(7)10(14)11-6-9(12)13/h2-5H,6H2,1H3,(H,11,14)(H,12,13)/p-1

Upstream product

• 933-88-0 ortho-toluoyl chloride 
• 78973-74-7 N-o-toluoyl-glycine ethyl ester 
• 56-40-6 glycine 

Downstream Products

• 72615-40-8 2-m-Tolyl-4-[1-o-tolyl-meth-(Z)-ylidene]-4H-oxazol-5-one 
• 1268528-43-3 C₆₃H₆₇N₁₇O₁₁ 
• 1224962-86-0 C₁₂H₁₃NO₄ 
• 313645-46-4 4-(4-nitrobenzylidene)-2-(2-methylphenyl)-5(4H)-oxazolone 
• 313645-49-7 4-(4-methoxybenzylidene)-2-(2-methylphenyl)-5(4H)-oxazolone 
• 118-90-1 ortho-methylbenzoic acid 
• 78973-74-7 N-o-toluoyl-glycine ethyl ester 
• 1447964-05-7 (Z)-4-(2-(piperidin-1-yl)benzylidene)-2-o-tolyloxazol-5(4H)-one 
• 376392-00-6 N-[2-(1,4-diazabicyclo[3.2.2]non-4-yl)-2-oxoethyl]-2-methylbenzamide 
• 1361249-71-9 [(2-methylbenzoyl)amino]methyl acetate 
• 72615-39-5 2-o-Tolyl-4-[1-o-tolyl-meth-(Z)-ylidene]-4H-oxazol-5-one 
• 53949-13-6 (Z)-2-phenyl-4-(2-methylbenzylidene)-(4H)-1,3-oxazol-5-one 
• 72615-41-9 2-p-Tolyl-4-[1-o-tolyl-meth-(Z)-ylidene]-4H-oxazol-5-one 

Relevant articles and documents

Synthesis and evaluation of new phenyl acrylamide derivatives as potent non-nucleoside anti-HBV agents

As a continuation of our previous work, a series of new phenyl acrylamide derivatives (4Aa-g, 4Ba-t, 5 and 6a-c) were designed and synthesized as non-nucleoside anti-HBV agents. Among them, compound 4Bs could potently inhibit HBV DNA replication in wild-type and lamivudine (3TC)/entecavir resistant HBV mutant strains with IC50 values of 0.19 and 0.18 μM, respectively. Notably, the selective index value of 4Bs was above 526, indicating the favorable safety profile. Interestingly, unlike nucleoside analogue 3TC, 4Bs could significantly inhibit 3.5 kb pgRNA expression. Molecular docking study revealed that 4Bs could fit well into the dimer-dimer interface of HBV core protein by hydrophobic, π–π and H-bond interactions. Considering the potent anti-HBV activity, low toxicity and diverse anti-HBV mechanism from that of nucleoside anti-HBV agent 3TC, compound 4Bs might be a promising lead to develop novel non-nucleoside anti-HBV therapeutic agents, and warranted further investigation.

Palladium-catalyzed ortho-arylation of benzoic acid derivatives via C-H bond activation using an aminoacetic acid bidentate directing group

A highly efficient protocol for the palladium-catalyzed ortho-arylation of benzoic acid derivatives by aryl iodides is described with an aminoacetic acid based N,O bidentate directing group. This protocol can be applied to various benzoyl aminoacetic acids and aryl iodides with both electron-donating and electron-withdrawing groups. Remarkably, the nature of a new directing group drives selective C-H bond activation to afford only monoarylation products in good to excellent yields.

Substituents effect on the erlenmeyer-ploechl reaction: Understanding an observed process reaction time

A systematic study on hippuric acid substituents was performed in order to better understand the influence of stereoelectronic factors on the Erlenmeyer reaction rate. In addition, two reaction systems were evaluated: Huenig's base solvent free conditions and catalytic sodium acetate in 2-methyl-THF. The effect on reaction rate of electron withdrawing and electron donating groups are reported. Specifically, the study led to the conclusion that stereoelectronic factors have significant influence in one of our key Erlenmeyer reaction by affecting its reaction rate.