4-Aminohippuric acid Chemical Properties

Melting point:

199-200 °C (dec.)(lit.)

Boiling point:

330.62°C (rough estimate)

Density 

1.356

refractive index 

1.5600 (estimate)

storage temp. 

Store below +30°C.

solubility 

DMF: 33 mg/ml; DMF:PBS (pH7.2) (1:30): 0.03 mg/ml; DMSO: 20 mg/ml

form 

Crystalline Powder

pka

pKa 3.8 (Uncertain)

color 

Off-white to grayish

PH

3.0-3.5 (20g/l, H2O, 20℃)

Water Solubility 

Soluble in alcohol, chloroform, benzene, and acetone. Insoluble in water, ether, carbon, and tetrachloride.

Merck 

14,442

BRN 

1213676

InChIKey

HSMNQINEKMPTIC-UHFFFAOYSA-N

CAS DataBase Reference

61-78-9(CAS DataBase Reference)

EPA Substance Registry System

P-Aminohippuric acid (61-78-9)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-20/21/22

Safety Statements 

37/39-26-36

WGK Germany 

3

F 

8-9-23

TSCA 

Yes

HS Code 

29242990

Hazardous Substances Data

61-78-9(Hazardous Substances Data)

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

4-Aminohippuric acid Usage And Synthesis

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

muscle relaxant (smooth)

Uses

p-Aminohippuric acid has been used as infusions to measure plasma flow.

Uses

4-Aminohippuric Acid is used in the measurement of renal plasma flow as a diagnostic tool which may be applied towards kidney disorders.

Definition

ChEBI: P-aminohippuric acid is an N-acylglycine that is the 4-amino derivative of hippuric acid; used as a diagnostic agent in the measurement of renal plasma flow. It has a role as a Daphnia magna metabolite. It is a conjugate acid of a p-aminohippurate.

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.

Synthesis

4-Aminohippuric acid is prepared by reacting p-nitrobenzoyl chloride with glycine, followed by reducing the p-nitro group with tin and hydrochloric acid.

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.]

References

[1] B. ZMBOVA . Synthesis of p-aminohippuric acid analog and its labeling by technetium-99m[J]. International Journal of Radiation Applications and Instrumentation. Part A. Applied Radiation and Isotopes, 1989, 40 3: Pages 225-234. DOI:10.1016/0883-2889(89)90152-4.
[2] W P DEISS P P C. Studies in para-aminohippuric acid synthesis in the human: its application as a liver function test.[J]. Journal of Clinical Investigation, 1950, 29 8: 1014-1020. DOI:10.1172/JCI102332.
[3] M. SHEAT M. M Zenab F Saeed. Synthesis of Some of Azo, Triazines and Schiff Bases Compounds from 4-Aminohippuric Acid[J]. Journal of Education Science, 2009, 47 1: 1-8. DOI:10.33899/edusj.2009.57930.
[4] T SEKINE. Expression cloning and characterization of a novel multispecific organic anion transporter.[J]. The Journal of Biological Chemistry, 1997, 272 30: 18526-18529. DOI:10.1074/jbc.272.30.18526.
[5] HIROSHI UCHINO . p-Aminohippuric Acid Transport at Renal Apical Membrane Mediated by Human Inorganic Phosphate Transporter NPT1[J]. Biochemical and biophysical research communications, 2000, 270 1: Pages 254-259. DOI:10.1006/bbrc.2000.2407.

4-Aminohippuric acid(61-78-9)Related Product Information

• L-Tetrahydrofolic Acid
• Folic acid
• Aminopterin
• P-NITROBENZOYL-L-GLUTAMIC ACID
• 4-Aminohippuric acid
• P-AMINOHIPPURIC ACID SODIUM SALT
• N-(p-Aminobenzoyl)glutamic acid
• METHOTREXATE HYDRATE
• 5-METHYLTETRAHYDROFOLIC ACID DISODIUM SALT
• diethyl N-[4-(methylamino)benzoyl]-L-glutamate
• DIHYDROFOLIC ACID
• N-(4-AMINOBENZOYL)-L-GLUTAMIC ACID DIETHYL ESTER
• 4-NITROHIPPURIC ACID
• Calcium folinate
• (+/-)AMETHOPTERIN
• P-AMINOHIPPURIC ACID SODIUM
• Hippuric acid
• Uric acid