61-78-9

Basic information

• Product Name: 4-AMINOHIPPURIC ACID
• Synonyms: |p|-AMinohippuric acid (PAH);2-[(4-aminophenyl)carbonylamino]ethanoic acid;2-[[(4-aminophenyl)-oxomethyl]amino]acetic acid;Aminohippuric acid [USAN];Hippuric acid, p-amino-;Hippuric acid, p-amino- (8CI);N-[(4-aminophenyl)carbonyl]glycine;Nefrotest
• CAS NO: 61-78-9
• Molecular Formula: C₉H₁₀N₂O₃
• Molecular Weight: 194.19
• EINECS: 200-518-9
• Product Categories: TRASENTINE;Amino Acids
• Mol File: 61-78-9.mol
• Article Data: 7

Chemical Properties

• Melting Point: 199-200 °C (dec.)(lit.)
• Boiling Point: 330.62°C (rough estimate)
• Flash Point: 266.6 °C
• Appearance: Off-white to grayish/Crystalline Powder
• Density: 1.356
• Vapor Pressure: 1.6E-11mmHg at 25°C
• Refractive Index: 1.5600 (estimate)
• Storage Temp.: −20°C
• PKA: pKa 3.8 (Uncertain)
• Water Solubility: Soluble in alcohol, chloroform, benzene, and acetone. Insoluble in water, ether, carbon, and tetrachloride.
• Merck: 14,442
• BRN: 1213676
• CAS DataBase Reference: 4-AMINOHIPPURIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 4-AMINOHIPPURIC ACID(61-78-9)
• EPA Substance Registry System: 4-AMINOHIPPURIC ACID(61-78-9)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 37/39-26-36
• WGK Germany: 3
• F: 8-9-23
• TSCA: Yes
• Hazardous Substances Data: 61-78-9(Hazardous Substances Data)

Usage

Description

4-Aminohippuric acid is a substrate for various renal transporters that has been used in the study of anion uptake in the kidney. It is a substrate for organic anion transporter 1 (OAT1; Km = 14.3 μM in X. laevis oocytes), the human inorganic phosphate transporter (NPT1; Km = 2.66 mM in HEK293 cells), and apical multidrug resistance protein (MDR2; Km = 880 μM in HEK293 cells). 4-Aminohippuric acid is a glycine amide form of 4-aminobenzoic acid . Formulations containing 4-aminohippuric acid have been used as markers to determine renal plasma flow.

Chemical Properties

off-white to greyish crystalline powder

Uses

Different sources of media describe the Uses of 61-78-9 differently. You can refer to the following data:
1. 4-Aminohippuric Acid is used in the measurement of renal plasma flow as a diagnostic tool which may be applied towards kidney disorders.
2. p-Aminohippuric acid has been used as infusions to measure plasma flow.

Definition

ChEBI: An N-acylglycine that is the 4-amino derivative of hippuric acid; used as a diagnostic agent in the measurement of renal plasma flow.

General Description

Renal tubules secretes para amino hippuric acid/PAH.

Biochem/physiol Actions

Para-aminohippuric acid?(PAH) is used as a marker in nutrition studies to measure the flow of blood in pigs, which inturn helps to determine the portal-drained viscera (PDV) flux of nutrients.

Purification Methods

Crystallise the acid from H2O. It is soluble in organic solvents. [Cohen & McGilvery J Biol Chem 169 119 1945, 171 121 1947, Meunzen et al. J Biol Chem 26 469 1926, Beilstein 14 III 1069, 14 IV 1152.]

InChI:InChI=1/C9H10N2O3/c10-7-3-1-6(2-4-7)9(14)11-5-8(12)13/h1-4H,5,10H2,(H,11,14)(H,12,13)/p-1

Upstream product

• 2645-07-0 4-nitrohippuric acid 
• 62-23-7 4-nitro-benzoic acid 
• 2644-96-4 2-(4-nitrobenzamido)acetic acid methyl ester 
• 122-04-3 4-nitro-benzoyl chloride 
• 150-13-0 4-amino-benzoic acid 
• 56-40-6 glycine 
• 16106-38-0 4-aminobenzoyl chloride 

Downstream Products

• 70674-94-1 N-[4-(N'-allyl-thioureido)-benzoyl]-glycine 
• 101248-38-8 methyl N-(4-aminobenzoyl)glycinate hydrochloride 
• 83560-86-5 N-(2,3-dimethylmaleimido) hippuric acid 
• 1242060-32-7 C₁₅H₁₆N₆O₅ 
• 1446010-68-9 2-(4-(3-butylthioureido)benzamido)acetic acid 
• 1446010-69-0 2-(4-(3-cyclohexylthioureido)benzamido)acetic acid 
• 59440-81-2 2-(4-(3-phenylthioureido)benzamido)acetic acid 
• 1446010-70-3 2-(4-(3-(3-bromophenyl)thioureido)benzamido)acetic acid 
• 1446010-71-4 2-(4-(3-p-tolylthioureido)benzamido)acetic acid 
• 1446010-72-5 2-(4-(3-(3-fluorophenyl)thioureido)benzamido)acetic acid 
• 1446010-73-6 2-(4-(3-(4-fluorophenyl)thioureido)benzamido)acetic acid 
• 1446010-74-7 2-(4-(3-acridin-9-ylthioureido)benzamido)acetic acid 
• 1446010-75-8 2-(4-(3-(2-(3-(trifluoromethyl)phenylcarbamoyl)phenyl)thioureido)benzamido)acetic acid 
• 1446010-76-9 2-(4-(3-(2-(4-ethoxyphenylcarbamoyl)phenyl)thioureido)benzamido)acetic acid 

Relevant articles and documents

Preparation method of C.I. red pigment 170 derivative and application in producing special F3RK of water-borne coating

The invention relates to a preparation method, in particular to a preparation method of C.I. red pigment 170 derivative and application in producing special F3RK. The preparation method has the advantages that by adding a molecular structure and a similar derivative containing a hydrophilic group into a heavy nitrogen fraction, the synthesized pigment is more hydrophilic, so that the pigmentation is realized at normal temperature; the operation environment is improved, the labor cost is reduced, and the special pigment F3RK for a water-borne coating is obtained.

Advanced glycation inhibitors containing amino-benzoic acids and derivatives, and methods of use

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Synthesis and in Vitro Aldolase Reductase Inhibitory Activity of Compounds Containing an N-Acylglycine Moiety

A number of N-benzoylglycines (6), N-acetyl-N-phenylglycines (7), N-benzoyl-N-phenylglycines (8), and tricyclic N-acetic acids (9-12) were synthesized as analogues of the N-acylglycine-containing aldolase reductase inhibitors alrestatin and 2-oxoquinoline-1-acetic acid.Derivatives of 6, which represent ring-simplified analogues of alrestatin, are very weak inhibitors of aldolase reductase obtained from rat lens, producing 50percent inhibition only at concentrations exceeding 100 μM.Compounds of series 7 were designed as ring-opened analogues of the 2-oxoquinolines.While this derivatives are more potent than compounds of series 6 (IC 50s of 6-80 μM), they are less active than the corresponding 2-oxoquinolines.Analogues of series 8 were designed as hybrid structures of both alrestatin and the 2-oxoquinoline-1-acetic acids.These compounds are substantially more potent than compounds of series 6 and 7 and display inhibitory activities comparable to or greater than alrestatin or the 2-oxoquinolines (IC 50s of 0.1-10 μM).Of the rigid analogues of 8, the most potent derivative is benzoxindol (12) with an IC 50 of 0.67 μM, suggesting that fusion of the two aromatic rings of 8 in a coplanar conformation may optimize affinity for aldose reductase in this series.