Aminohippuric acid

Base Information

• Chemical Name: Aminohippuric acid
• CAS No.: 61-78-9
• Molecular Formula: C9H10N2O3
• Molecular Weight: 194.19
• Hs Code.: DERIVATION
• European Community (EC) Number: 200-518-9
• NSC Number: 758232,13064,7550
• UNII: Y79XT83BJ9
• DSSTox Substance ID: DTXSID7022590
• Nikkaji Number: J38.133K
• Wikipedia: Aminohippuric_acid
• Wikidata: Q291271
• NCI Thesaurus Code: C76046
• RXCUI: 7832
• Metabolomics Workbench ID: 37899
• ChEMBL ID: CHEMBL463
• Mol file: 61-78-9.mol

Synonyms:4 Aminohippuric Acid;4-Aminohippuric Acid;Aminohippurate Sodium;Aminohippuric Acid;Nephrotest;p Aminohippurate;p Aminohippuric Acid;p-Aminohippurate;p-Aminohippuric Acid;para Aminohippuric Acid;Para-Aminohippurate, Sodium;para-Aminohippuric Acid;Sodium Para Aminohippurate;Sodium Para-Aminohippurate;Sodium, Aminohippurate

Chemical Property of Aminohippuric acid

Chemical Property:

• Appearance/Colour: off-white to greyish crystalline powder
• Vapor Pressure: 1.6E-11mmHg at 25°C
• Melting Point: 199-200 °C (dec.)(lit.)
• Refractive Index: 1.5600 (estimate)
• Boiling Point: 517.2 °C at 760 mmHg
• PKA: pKa 3.8 (Uncertain)
• Flash Point: 266.6 °C
• PSA: 92.42000
• Density: 1.356 g/cm³
• LogP: 1.05530
• Storage Temp.: −20°C
• Water Solubility.: Soluble in alcohol, chloroform, benzene, and acetone. Insoluble in water, ether, carbon, and tetrachloride.
• XLogP3: -0.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 194.06914219
• Heavy Atom Count: 14
• Complexity: 222

Purity/Quality:

99% ^*data from raw suppliers

PAH ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 37/39-26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Amino Carboxylic Acids
• Canonical SMILES: C1=CC(=CC=C1C(=O)NCC(=O)O)N
• Recent ClinicalTrials: Mechanisms Underlying Hypotensive Response to ARB/NEP Inhibition - Aim 2
• Recent EU Clinical Trials: A multicenter, randomized, double-blind, parallel group, placebo-controlled study to evaluate the renal hemodynamic effects of RLX030 at a dose of 30 μg/kg/day or placebo infused for 24 hours in subjects with chronic heart failure (CHF).
• 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.
• Uses: 4-Aminohippuric Acid is used in the measurement of renal plasma flow as a diagnostic tool which may be applied towards kidney disorders. p-Aminohippuric acid has been used as infusions to measure plasma flow.

Technology Process of Aminohippuric acid

There total 8 articles about Aminohippuric acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 50.0%

2-(4-nitrobenzamido)acetic acid methyl ester (2644-96-4) → p-Aminohippuric acid (61-78-9)

Guidance literature:

With methanol; acetic acid; zinc; In water; for 3h; Reflux;

Reference yield:

4-nitrohippuric acid (2645-07-0) → p-Aminohippuric acid (61-78-9)

Guidance literature:

With ethanol; nickel; Hydrogenation;

Reference yield:

4-nitro-benzoyl chloride (122-04-3) → p-Aminohippuric acid (61-78-9)

Guidance literature:

Multi-step reaction with 2 steps

1: NaOH / H₂O / 0.5 h / Ambient temperature

2: H₂ / 5percent Pd-C / ethanol / 0.5 h / 2327.2 Torr

With sodium hydroxide; hydrogen; palladium on activated charcoal; In ethanol; water;

DOI:10.1021/jm00111a030

upstream raw materials:

4-nitrohippuric acid

4-amino-benzoic acid

glycine

4-aminobenzoyl chloride

Downstream raw materials:

N-[4-(N'-allyl-thioureido)-benzoyl]-glycine

4-(3-acetoxy-benzylidene)-2-(4-acetylamino-phenyl)-4H-oxazol-5-one

p-<(p-methoxybenzylidene)amino>hippuric acid

({[4-(4-methyl-1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)phenyl]carbonyl}amino)acetic acid

Refernces

• 1、 -. "4-substituted anilinoquinazoline derivatives, and preparation method and application thereof". Paragraph 0042; 0043. . Retrieved 2017/01/31.
• 2、 DeRuiter, Jack,Davis, R. Alan,Wandrekar, Vinay G.,Mayfield, Charles A.. "Relative Structure-Inhibition Analyses of the N-Benzoyl and N-(Phenylsulfonyl) Amino Acid Aldose Reductase Inhibitors". . p. 2120 - 2126. Retrieved 2007/10/02.