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

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

Uses

Used in Medical Diagnostics:
4-Aminohippuric acid is used as a diagnostic tool for measuring renal plasma flow, which is essential in the assessment of kidney function and disorders. It aids in the evaluation of the efficiency of the kidneys in filtering blood and can help identify potential issues within the renal system.
Used in Pharmaceutical Research:
As a substrate for organic anion transporter 1 (OAT1), the human inorganic phosphate transporter (NPT1), and apical multidrug resistance protein (MDR2), 4-aminohippuric acid plays a crucial role in pharmaceutical research. It helps scientists understand the mechanisms of renal transport and develop new drugs and therapies targeting the renal system.
Used in Infusion Therapy:
4-Aminohippuric acid has been used in infusions to measure plasma flow, providing valuable information on the circulatory system's efficiency and overall cardiovascular health. This application is particularly useful in monitoring and managing patients with conditions that affect blood flow and vascular function.

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

Downstream Products

• 20333-85-1 N-(4-amino-benzoyl)-glycine ethyl ester 
• 90290-83-8 2-(4-cyanobenzamido)acetic acid 
• 69104-89-8 N-(4-amino-3,5-diiodo-benzoyl)-glycine 
• 70674-94-1 N-[4-(N'-allyl-thioureido)-benzoyl]-glycine 
• 16247-12-4 p-Phosphino-acetyl-amino-hippursaeure 
• 67726-11-8 N-{4-[(2-oxo-benzooxazol-3-ylmethyl)-amino]-benzoyl}-glycine 
• 67726-16-3 N-{4-[(2-thioxo-benzooxazol-3-ylmethyl)-amino]-benzoyl}-glycine 
• 67726-22-1 N-{4-[(2-thioxo-benzothiazol-3-ylmethyl)-amino]-benzoyl}-glycine 
• 18207-37-9 4-(4-acetoxy-benzylidene)-2-(4-acetylamino-phenyl)-4H-oxazol-5-one 
• 18114-52-8 4-(3-acetoxy-benzylidene)-2-(4-acetylamino-phenyl)-4H-oxazol-5-one 
• 18114-50-6 2-(4-acetylamino-phenyl)-4-(2-chloro-benzylidene)-4H-oxazol-5-one 
• 18114-51-7 2-(4-acetylamino-phenyl)-4-(3-nitro-benzylidene)-4H-oxazol-5-one 
• 18114-53-9 2-(4-acetylamino-phenyl)-4-(4-nitro-benzylidene)-4H-oxazol-5-one 
• 18210-88-3 4-(4-acetylamino-benzylidene)-2-(4-acetylamino-phenyl)-4H-oxazol-5-one 

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.

4-substituted anilinoquinazoline derivatives, and preparation method and application thereof

The invention discloses novel 4-substituted anilinoquinazoline derivatives or pharmaceutically acceptable salts thereof, or polymorphic substances, solvates or stereomers of the 4-substituted anilinoquinazoline derivatives, and a preparation method and application thereof. The 4-substituted anilinoquinazoline compounds have favorable inhibition activities for EGFR and VEGFR-2 in a biological test and have obvious effects in an in-vitro anti-human tumor cell proliferation activity test.

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

The present invention relates to compositions and methods for inhibiting nonenzymatic cross-linking (protein aging). Accordingly, a composition is disclosed which comprises an agent capable of inhibiting the formation of advanced glycosylaton endproducts of target proteins by reacting with the carbonyl moiety of the early glycosylation product of such target proteins formed by their initial glycosylation. The method comprises contacting the target protein with the composition. Both industrial and therapeutic applications for the invention are envisioned, as food spoilage and animal protein aging can be treated.

Relative Structure-Inhibition Analyses of the N-Benzoyl and N-(Phenylsulfonyl) Amino Acid Aldose Reductase Inhibitors

A number of N-benzoyl amino acids were synthesized and tested to compare structure-inhibition relationships with the isosteric N-(phenylsulfonyl) amino acid (PS-amino acid) aldose reductase inhibitors.Inhibition analyses with these series reveals that their kinetic mechanisms of inhibition are similar, but that significant differences in structure-inhibition relationships exist.For example, while the PS-alanines and PS-2-phenylglycines produce enantioselective inhibition (S > R), no consistent pattern of enantioselectivity is observed with the isosteric N-benzoylalanines and 2-phenylglycines.Also, N-methyl and N-phenyl substitution in the PS-amino acid series does not substantially alter inhibitory activity, while similar substitutions in the N-benzoyl series (particularly N-phenyl) results in a significant increase in inhibitory activity.Proton NMR analysis of the N-benzoylsarcosines reveals that these compounds exist as a mixture of rotamers in solutions including the enzyme assay buffer and that the preferred conformer is one in which the carboxymethyl moiety is trans to the aromatic ring.Similar analyses with the N-benzoyl-N-phenylglycines demonstrate that these derivatives exist exclusively in the trans rotameric conformation in solution.No such N-substituent effects on conformation were observed in the PS-amino acid series.These results suggest that the differences in structure-inhibition trends between these structurally related series may result from the effect of substituents on preferred conformation.

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.

Method of suppressing body odor with aminobenzoic acid amides

This invention is directed to a cosmetic deodorant composition comprising: (a) from about 0.1 to 5 percent by weight, based on the weight of the total composition, of aminobenzoic acid amides of the formula STR1 wherein R1 and R2, which may be the same or different, each represent hydrogen, an alkyl of from 1 to 12 carbon atoms; a hydroxyalkyl of from 2 to 4 carbon atoms; an aryl; an aralkyl or carboxyalkyl with from 1 to 3 carbon atoms in the alkyl moiety; or an alkoxyalkyl with from 1 to 8 carbon atoms in the alkoxy moiety and from 1 to 3 carbon atoms in the alkyl moiety, or R1 and R2 together with the amide nitrogen form an optionally substituted heterocyclic ring; and (b) the remainder conventional cosmetic deodorant composition compounds.

Radiopharmaceutical composition based on technetium-99m and reagent for making it

Radiopharmaceutical compositions containing complexes of technetium-99m with a complexing agent are prone to time and activity-related decomposition and formation of pertechnetate. Stabilizing agents for such complexes are organic compounds having an amine group and a carboxylic acid group attached to an aromatic ring. A preferred stabilizing agent is the sodium salt of 4-aminobenzoic acid. There are claims to a composition comprising a technetium 99-m complex stabilized by means of the said stabilizing agent; and to a reagent which forms, on addition of an aqueous solution of pertechnetate, a radiopharmaceutical composition, which reagent comprises a tin metal or stannous reducing agent for the pertechnetate, a complexing agent for the reduced technetium, for example a phosphorus-containing bone scanning agent, and a stabilizing agent as defined.