4-Aminohippuric acid Property

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

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)

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

4-Aminohippuric acid Chemical Properties,Usage,Production

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.