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| | 4-Aminohippuric acid 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);Nefrotest;N-[(4-aminophenyl)carbonyl]glycine | | CAS: | 61-78-9 | | MF: | C9H10N2O3 | | MW: | 194.19 | | EINECS: | 200-518-9 | | Product Categories: | TRASENTINE;Amino Acids | | Mol File: | 61-78-9.mol |  |
| | 4-Aminohippuric acid Chemical Properties |
| Melting point | 199-200 °C (dec.)(lit.) | | Boiling point | 330.62°C (rough estimate) | | bulk density | 380kg/m3 | | 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 | | pka | pKa 3.8 (Uncertain) | | form | Crystalline Powder | | 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 | | Major Application | cell analysis | | InChI | 1S/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) | | InChIKey | HSMNQINEKMPTIC-UHFFFAOYSA-N | | SMILES | Nc1ccc(cc1)C(=O)NCC(O)=O | | CAS DataBase Reference | 61-78-9(CAS DataBase Reference) | | EPA Substance Registry System | P-Aminohippuric acid (61-78-9) |
| | 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 | p-Aminohippuric acid has been used as infusions to measure plasma flow. | | Uses | muscle relaxant (smooth) | | 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 Preparation Products And Raw materials |
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