2-(phenylformamido)acetic acid

• ChemBase ID: 34688
• Molecular Formular: C9H9NO3
• Molecular Mass: 179.17266
• Monoisotopic Mass: 179.05824315
• SMILES: C(=O)(NCC(=O)O)c1ccccc1
• Canonical SMILES: O=C(c1ccccc1)NCC(=O)O
• InChI: InChI=1S/C9H9NO3/c11-8(12)6-10-9(13)7-4-2-1-3-5-7/h1-5H,6H2,(H,10,13)(H,11,12)
• InChIKey: QIAFMBKCNZACKA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(phenylformamido)acetic acid
• IUPAC Traditional name: hippuric acid
• Synonyms: (Benzoylamino)acetic acid; Hippuric acid; 2-(Benzoylamino)acetic Acid; 2-Benzamidoacetic Acid; (Benzoylamino)-acetic Acid; Benzamidoacetic Acid; Benzoyl Glycocoll; Benzoylglycine; NSC 9982; Phenylcarbonylaminoacetic Acid; N-Benzoylglycine; Benzoylaminoacetic acid; HIPPURIC ACID FREE ACID; Hippuric acid; N-benzoylglycind; benzoyl glycocold; benzoyl amidoacetic acid; Hippuric acid; 2-benzamidoacetic acid; 苯甲酰氨基乙酸; 马尿酸

Database IDs

• CAS Number: 495-69-2
• EC Number: 207-806-3
• MDL Number: MFCD00002692
• Beilstein Number: 1073987
• Merck Index: 144716
• PubChem SID: 24847057; 160997995; 24877916
• PubChem CID: 464
• CHEBI ID: 18089
• CHEMBL: 461
• Chemspider ID: 451
• KEGG ID: C01586
• Unique Ingredient Identifier: TE0865N2ET
• Wikipedia Title: Hippuric_acid

CALCULATED PROPERTIES

• Acid pKa: 3.5912387
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -1.3782724
• LogD (pH = 7.4): -2.8205347
• Log P: 0.5255455
• Molar Refractivity: 46.1177 cm^3
• Polarizability: 17.405828 Å^3
• Polar Surface Area: 66.4 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 187 - 188 °C; 187-191 °C; 187-191 °C(lit.); 188-191°C; 188-191°C; 190-192°C
• Boiling Point: 240 °C (dec.)
• Density: 1.371

Safety Information

• Storage Condition: Refrigerator; Room Temperature (15-30°C)
• Storage Warning: IRRITANT
• RTECS: MR8150000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-37/38-41
• Safety Statements: 26-39
• TSCA Listed: false; 是
• GHS Pictograms: GHS05; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H302-H315-H318-H335
• GHS Precautionary statements: P261-P280-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Pharmacology Properties

• Gene Information: rat ... Akr1b1(24192)

Product Information

• Purity: ~99%; ≥97.0% (T); 98%
• Linear Formula: C6H5CONHCH2COOH

DETAILS

MP Biomedicals - 02100115

Free Acid
Crystalline
Purity: ~99%

Sigma Aldrich - 112003

Packaging
100, 500 g in poly bottle
5 g in glass bottle
Application
Hippuric acid can be used to study cell biology, chemical biology, bioactive small molecules, amino acid derivatives, peptide synthesis, chemical synthesis and nutrition. Hippuric acid has been used to inform the metabolism and urinary excretion of procyanidins.

Toronto Research Chemicals - H356700

N-Benzoylglycine also known as Hippuric Acid is the glycine conjugate of benzoic acid commonly found in ruminant urine. Hippuric acid is synthesized in the liver and its production is greatly increased following consumption of benzoic acid. In itself it d

REFERENCES

• Jankowski J. T. et. al.: Kidney Int. 78, 84 (2001)
• For cyclization with acetic anhydride to 2-phenyl-5-oxazolone, see: Org. Synth. Coll., 5, 946 (1973).
• Condensation with aldehydes gives azlactones, which are intermediates in a classical route to amino acids; see, e.g.: Org. Synth. Coll., 2, 489 (1943). An alternative approach involves alkylation of the trianion of hippuric acid, prepared by LDA/TMEDA in THF: Tetrahedron Lett., 2205 (1976).