27115-50-0

Basic information

• Product Name: 4-METHYLHIPPURIC ACID
• Synonyms: PARA-METHYLHIPPURICACID;4-METHYLHIPPURIC ACID 98%;N-(4-Methylbenzoyl)glycine, p-Toluric acid;p-Methylbenzoylaminoacetic acid;4-Methylhippuric acid,98%;N-(p-Methylbenzoyl)glycine;NSC 126814;N-(4-Methylbenzoyl)glycine-d7
• CAS NO: 27115-50-0
• Molecular Formula: C₁₀H₁₁NO₃
• Molecular Weight: 193.2
• EINECS: 248-231-8
• Product Categories: Amines;Aromatics
• Mol File: 27115-50-0.mol
• Article Data: 27

Chemical Properties

• Melting Point: 163-165 °C(lit.)
• Boiling Point: 329.41°C (rough estimate)
• Flash Point: 217.3 °C
• Appearance: White crystalline powder
• Density: 1.2307 (rough estimate)
• Vapor Pressure: 1.58E-08mmHg at 25°C
• Refractive Index: 1.5300 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 3.72±0.10(Predicted)
• CAS DataBase Reference: 4-METHYLHIPPURIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 4-METHYLHIPPURIC ACID(27115-50-0)
• EPA Substance Registry System: 4-METHYLHIPPURIC ACID(27115-50-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26
• WGK Germany: 3
• Hazardous Substances Data: 27115-50-0(Hazardous Substances Data)

Usage

Description

4-METHYLHIPPURIC ACID, also known as a substituted hippurate analog, is an N-acylglycine in which the acyl group is specified as 4-methylbenzoyl. It is the major metabolite of xylene and has been determined in urine by gas chromatography. 4-METHYLHIPPURIC ACID is a white crystalline powder and is used as a substrate and inhibitor of peptidylglycine α-hydroxylating monooxygenase (PHM).

Uses

Used in Pharmaceutical Industry:
4-METHYLHIPPURIC ACID is used as a substrate and inhibitor for peptidylglycine α-hydroxylating monooxygenase (PHM) for studying enzyme activity and inhibition in the pharmaceutical industry. This application helps in understanding the enzyme's role in various biological processes and can contribute to the development of new drugs targeting this enzyme.
Used in Environmental and Occupational Health:
4-METHYLHIPPURIC ACID is used as a biomarker for exposure to xylene, an industrial solvent, in environmental and occupational health assessments. The detection of this metabolite in urine samples can indicate the level of exposure to xylene, which is crucial for monitoring worker safety and environmental contamination.
Used in Toxicology Research:
4-METHYLHIPPURIC ACID is used as a research tool in toxicology to study the metabolism and toxic effects of xylene and other related compounds. This application aids in understanding the mechanisms of toxicity and can help in the development of strategies to mitigate the harmful effects of these chemicals on human health and the environment.

InChI:InChI=1/C10H17NO3/c1-7-2-4-8(5-3-7)10(14)11-6-9(12)13/h7-8H,2-6H2,1H3,(H,11,14)(H,12,13)/p-1

Upstream product

• 122081-29-2 N-(4-methyl)benzoyl glycine ethylester 
• 874-60-2 4-methyl-benzoyl chloride 
• 56-40-6 glycine 
• 75152-18-0 2-p-tolyl-4H-oxazol-5-one 
• 99-94-5 p-Toluic acid 
• 22198-21-6 N-p-toluoyl-glycine nitrile 
• 42469-26-1 N-(2-hydroxyethyl)-4-methylbenzamide 

Downstream Products

• 122081-29-2 N-(4-methyl)benzoyl glycine ethylester 
• 72615-38-4 (4Z)-2-(4-methylphenyl)-4-(phenylmethylidene)-1,3-oxazol-5(4H)-one 
• 16352-80-0 4-furfurylidene-2-p-tolyl-4H-oxazol-5-one 
• 16352-78-6 4-benzo[1,3]dioxol-5-ylmethylene-2-p-tolyl-4H-oxazol-5-one 
• 75152-18-0 2-p-tolyl-4H-oxazol-5-one 
• 16352-74-2 4-(2-chloro-benzylidene)-2-p-tolyl-4H-oxazol-5-one 
• 16352-73-1 4-benzylidene-2-(4-methylphenyl)-1,3-oxazol-5(4H)-one 
• 16352-76-4 4-(3,4-dimethoxy-benzylidene)-2-p-tolyl-4H-oxazol-5-one 
• 16352-79-7 2-(p-Tolyl)-4-cinnamyliden-oxazolinon-(5) 
• 16352-77-5 4-(4-dimethylamino benzylidene)-2-p-tolyloxazol-5(4H)-one 
• 75152-14-6 (4-Methyl-benzoylamino)-acetic acid 4-nitro-phenyl ester 
• 116222-15-2 3-(4-Methyl-benzoylamino)-2-oxo-1,2-dihydro-quinoline-4-carboxylic acid phenylamide 
• 126325-45-9 N-(8-Hydroxy-2-oxo-2H-chromen-3-yl)-4-methyl-benzamide 
• 116222-16-3 3-(4-Methyl-benzoylamino)-2-oxo-1,2-dihydro-quinoline-4-carboxylic acid cyclohexylamide 

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.

Supported ruthenium hydride catalysts for direct conversion of alcohols to carboxylic acids using styrene oxide as oxidant

In the present work, the ability of two ruthenium hydride catalysts supported on multiwall carbon nanotubes, [Ru–H@EDT–MWCNT], and gold nanoparticles cored triazine dendrimer, [Ru–H@AuNPs–TD], in the direct conversion of alcohols to carboxylic acids via transfer hydrogenation using styrene oxide as oxidant is reported. Different alcohols were successfully converted to their corresponding carboxylic acids. The results showed that these two heterogeneous catalysts are more efficient than the homogeneous counterpart. In addition, the catalysts were reused several times.

Synthesis and cytotoxicity of novel dispiro derivatives of 5-arylidenoxazolones, potential inhibitors of p53—MDM2 protein-protein interaction

Regioselective synthesis of new dispiro indolinones combining both an indolinone and an oxazolone fragment in their structure comprised the 1,3-dipolar cycloaddition of azomethine ylides, generated in situ from isatin and sarcosine, at 2-aryl-5-arylmethylidene-substituted 1,3-oxazol-5(4H)-ones. When ortho and para halogen atoms were present in the aromatic substituents of the starting oxazolones, complex mixtures containing large amounts of oxazoline ring opening products and their dispiro derivatives were formed. The cytotoxicity of compounds was tested by MTT on LNCaP, PC3, HCT116, MCF7, A549, HEK, and VA13 cell lines. The compound possessing the best cytotoxicity revealed the IC50 = 1.08±0.96 μM towards the p53- expressing LNCaP cells and lower activity (IC50 = 3.21±1.45 μM) towards the non-expressing p53 protein PC3 cells, however, it has proved inactive towards the HCT cells, both expressing (HCТ+/+) and non-expressing (HCT–/–) p53.