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4-Aminohippuric acid

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CAS:61-78-9
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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 Structure
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
pkapKa 3.8 (Uncertain)
form Crystalline Powder
color Off-white to grayish
PH3.0-3.5 (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
InChIKeyHSMNQINEKMPTIC-UHFFFAOYSA-N
CAS DataBase Reference61-78-9(CAS DataBase Reference)
EPA Substance Registry SystemP-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
8-9-23
TSCA Yes
HS Code 29242990
Hazardous Substances Data61-78-9(Hazardous Substances Data)
MSDS Information
ProviderLanguage
ACROS English
SigmaAldrich English
ALFA English
4-Aminohippuric acid Usage And Synthesis
Description4-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 Propertiesoff-white to greyish crystalline powder
Usesp-Aminohippuric acid has been used as infusions to measure plasma flow.
Usesmuscle relaxant (smooth)
Uses4-Aminohippuric Acid is used in the measurement of renal plasma flow as a diagnostic tool which may be applied towards kidney disorders.
DefinitionChEBI: 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 DescriptionRenal tubules secretes para amino hippuric acid/PAH.
Biochem/physiol ActionsPara-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.
Synthesis4-Aminohippuric acid is prepared by reacting p-nitrobenzoyl chloride with glycine, followed by reducing the p-nitro group with tin and hydrochloric acid.
Purification MethodsCrystallise 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
Raw materials4-Nitrobenzoyl chloride-->Glycine-->Tin-->Hydrochloric acid
Tag: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