4-Hydroxyhippuric acid

Base Information

• Chemical Name: 4-Hydroxyhippuric acid
• CAS No.: 2482-25-9
• Molecular Formula: C9H9NO4
• Molecular Weight: 195.175
• Hs Code.: 2924299090
• European Community (EC) Number: 822-262-2
• UNII: 4E2MH5995F
• DSSTox Substance ID: DTXSID50179518
• Nikkaji Number: J628.629A
• Wikidata: Q27139257
• Metabolomics Workbench ID: 42473
• ChEMBL ID: CHEMBL500596
• Mol file: 2482-25-9.mol

Synonyms:4-hydroxybenzoylglycine;4-hydroxyhippuric acid;N-(4-hydroxybenzoyl)glycine;p-hydroxyhippuric acid

Chemical Property of 4-Hydroxyhippuric acid

Chemical Property:

• Vapor Pressure: 1.77E-11mmHg at 25°C
• Melting Point: 240 °C (decomp)
• Refractive Index: 1.604
• Boiling Point: 516.2 °C at 760 mmHg
• PKA: 3.57±0.10(Predicted)
• Flash Point: 266 °C
• PSA: 86.63000
• Density: 1.4g/cm³
• LogP: 0.59750
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: -0.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 195.05315777
• Heavy Atom Count: 14
• Complexity: 221

Purity/Quality:

97% ^*data from raw suppliers

4-HydroxyhippuricAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C(=O)NCC(=O)O)O
• Uses: Derivative of 4-Hydroxyhippuric Acid used as a probe for estimating the activities of organic anion transporter 3 (OAT3) and multidrug resistance-associated protein 4 (MRP4) which mediate the efflux of organic anion from the brain and heart in mouse.

Technology Process of 4-Hydroxyhippuric acid

There total 10 articles about 4-Hydroxyhippuric 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: 85.0%

4-hydroxybenzoyl chloride (28141-24-4) + glycine (56-40-6,18875-39-3,25718-94-9) → 4-hydroxyhippuric acid (2482-25-9)

Guidance literature:

In water;

DOI:10.1134/S1070363215090261

Reference yield: 77.0%

(4-methoxybenzoylamino)acetic acid methyl ester (62086-71-9) → 4-hydroxyhippuric acid (2482-25-9)

Guidance literature:

Reference yield:

4-hydroxy-benzoic acid (99-96-7) → 4-hydroxyhippuric acid (2482-25-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / triethylamine / toluene / 2 h / Heating

2: 60 percent / SOCl₂ / CH₂Cl₂ / 3 h / Heating

3: 2) ethyl acetate / 1) methylene chloride, 30 min, reflux, 2) THF

With thionyl chloride; ethyl acetate; triethylamine; In dichloromethane; toluene;

upstream raw materials:

N-(4-methoxycarbonyloxy-benzoyl)-glycine ethyl ester

N,O-bis(trimethylsilyl)glycine

4-(trimethylsilyloxy)benzoyl chloride

(4-methoxybenzoylamino)acetic acid methyl ester

Downstream raw materials:

N-(4-methoxybenzoyl)glycine

N-(4-hydroxy-3,5-diiodo-benzoyl)-glycine

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

glycine