1637-75-8

Usage

Uses

Used in Pharmaceutical Industry:
3-Hydroxyhippuric acid is used as a pharmaceutical intermediate for the synthesis of various drugs, including anti-inflammatory agents and other therapeutic compounds.
Used in Metabolism Research:
3-Hydroxyhippuric acid is used as a biomarker in the study of human metabolism, particularly in the metabolism of caffeic and chlorogenic acids. It can provide insights into the metabolic pathways and help in understanding the role of these compounds in health and disease.
Used in Toxicology Studies:
3-Hydroxyhippuric acid can be used in toxicology studies to assess the exposure to certain chemicals or drugs and their metabolites. Its presence in biological samples can indicate the extent of exposure and potential health risks associated with the substances.
Used in Analytical Chemistry:
3-Hydroxyhippuric acid can be used as a reference compound in analytical chemistry for the development and validation of analytical methods, such as chromatographic techniques and mass spectrometry, for the detection and quantification of related compounds in various matrices.

InChI:InChI=1/C9H9NO4/c11-7-3-1-2-6(4-7)9(14)10-5-8(12)13/h1-4,11H,5H2,(H,10,14)(H,12,13)

Upstream product

• 70799-63-2 3-(trimethylsiloxy)benzoyl chloride 
• 3782-84-1 3-trimethylsiloxybenzoic acid trimethylsilyl ester 
• 99-06-9 3-Carboxyphenol 
• 245555-64-0 3-ethoxycarbonyloxybenzoyl chloride 
• 56-40-6 glycine 
• 586-38-9 3-Methoxybenzoic acid 
• 1211-92-3 methyl 2-(3-methoxybenzamido)acetate 
• 623-33-6 glycine ethyl ester hydrochloride 
• 16446-73-4 3-(chlorocarbonyl)phenyl acetate 
• 20938-64-1 N-(3-Aminobenzoyl)glycine 

Downstream Products

• 99-06-9 3-Carboxyphenol 
• 56-40-6 glycine 
• 109866-43-5 2-(3-acetoxy-phenyl)-4-(4-dimethylamino-benzylidene)-4H-oxazol-5-one 

Relevant academic research and scientific papers

Discovery of N-(2-(Benzylamino)-2-oxoethyl)benzamide analogs as a novel scaffold of pancreatic β-cell protective agents against endoplasmic reticulum stress

Endoplasmic reticulum (ER) stress-induced pancreatic β-cell dysfunction and death play important roles in the development of diabetes. The 1,2,3-triazole derivative 1 is one of only a few structures that have thus far been identified that protect β cells against ER stress. However, this compound has narrow activity range and limited aqueous solubility. To overcome these, we designed and synthesized a new scaffold in which the triazole pharmacophore was substituted with a glycine-like amino acid. Structure–activity relationship studies on this scaffold identified a N-(2-(Benzylamino)-2-oxoethyl)benzamide analog WO5m that possesses β-cell protective activity against ER stress with much improved potency (maximal activity at 100% with EC50 at 0.1?±?0.01?μm) and water solubility. Identification of this novel β-cell protective scaffold thus provides a new promising modality for the treatment of diabetes.

Development of a QuEChERS-Based Stable-Isotope Dilution LC-MS/MS Method to Quantitate Ferulic Acid and Its Main Microbial and Hepatic Metabolites in Milk

Forage plants of the Poaceae family are grown as pasturage or used for the production of hay, straw, corn stover, etc. Although ferulic acid contents of grasses are generally high, the amount of ingested ferulic acid differs depending on the type of forage, resulting in varying contents of ferulic acid and its microbial and hepatic metabolites in milk. Concentrations and patterns of these metabolites may be used as markers to track different forages in livestock feeding. Therefore, we developed a stable isotope dilution assay to quantitate ferulic acid, 12 ferulic acid-based metabolites, p-coumaric acid, and cinnamic acid in milk. Because most analytes were not commercially available as stable isotope labeled standard compounds, they were synthesized as 13C- or deuterium-labeled standard compounds. A modification of the QuEChERS method, a Quick, Easy, Cheap, Effective, Rugged, and Safe approach usually applied to analyze pesticides in plant-based products, was used to extract the phenolic acids from milk. Determination was carried out by LC-ESI-MS/MS in scheduled multiple reaction monitoring modus. By using three different milk samples, the applicability of the validated approach was demonstrated.

Crystal structure of the Homo sapiens kynureninase-3-hydroxyhippuric acid inhibitor complex: Insights into the molecular basis of kynureninase substrate specificity

Homo sapiens kynureninase is a pyridoxal-5'-phosphate dependent enzyme that catalyzes the hydrolytic cleavage of 3-hydroxykynurenine to yield 3-hydroxyanthranilate and L-alanine as part of the tryptophan catabolic pathway leading to the de novo biosynthesis of NAD+. This pathway results in quinolinate, an excitotoxin that is an NMDA receptor agonist. High levels of quinolinate have been correlated with the etiology of neurodegenerative disorders such as AIDS-related dementia and Alzheimer's disease. We have synthesized a novel kynureninase inhibitor, 3-hydroxyhippurate, cocrystallized it with human kynureninase, and solved the atomic structure. On the basis of an analysis of the complex, we designed a series of His- 102, Ser-332, and Asn-333 mutants. The H102W/N333T and H102W/S332G/N333T mutants showed complete reversal of substrate specificity between 3-hydroxykynurenine and L-kynurenine, thus defining the primary residues contributing to substrate specificity in kynureninases.

Substrate Specificity and Stoichiometry of Nα-Benzyloxycarbonyl Amino Acid Urethane Hydrolase from Streptococcus faecalis R ATCC 8043

The substrate specificity of a new enzyme, Nα-benzyloxycarbonyl amino acid urethane hydrolase, was investigated.The enzyme hydrolyzed Nα-benzyloxycarbonyl-glycine and -alanine, and Nα-benzoyl-glycine and -alanine.Nα-benzyloxycarbonyl-glycine was hydrolyzed to give equimolar benzyl alcohol and glycine.Equimolar benzoic acid and glycine were produced from Nα-benzoyl-glycine by the enzyme reaction.The Km, k0, and k0/Km values were measured for several substrates.The k0 values varied widely with the amino acid residues.Nα-benzyloxycarbonyl-glycine and Nα-benzoyl-glycine produced relatively small changes in the Km values (0.36 ca. 0.10 mM) and the k0/Km values (99440 ca. 202000 M-1 sec-1).The rate of hydrolysis is significantly affected by electron-supplying substituents on the benzene ring.