Hippuric acid
Synonym(s):N-Benzoylglycine;Benzamidoacetic acid, Benzoylglycine, Benzoylaminoacetic acid;Benzoylaminoacetic acid;Hippuric acid
- CAS NO.:495-69-2
- Empirical Formula: C9H9NO3
- Molecular Weight: 179.17
- MDL number: MFCD00002692
- EINECS: 207-806-3
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-03-22 14:56:24
What is Hippuric acid?
Description
Hippuric acid, or N-benzoylglycine, is an amino acid derivative found in the urine of herbivorous animals. The name is derived from Greek hippos (horse) and ouron (urine). In 1829, the pioneering German chemist Justus von Liebig so named it because his research on the compound concentrated on horse urine.
Hippuric acid also occurs in avocadoes (Persea americana) and common beans (Phaseolus vulgaris). As its chemical name suggests, the compound is formed by the reaction of benzoic acid and glycine in the urine.
Later in the 19th century, von Liebig’s last student, Oscar Loew, also studied hippuric acid. In 1879, Loew wrote about the source of the acid in herbivores’ urine. According to an account of the article in the first volume of the Journal of the American Chemical Society (1879), quinic acid1 in hay turns into hippuric acid during digestion. This finding had previously been observed in 1863 by Eduard Lautemann, a student of another important German chemist, Hermann Kolbe.
Synthetic hippuric acid is produced similarly to the biochemical reaction: Glycine is acylated with benzoyl chloride in the presence of base, followed by acidification to form the acid. Hydrolysis in strong base restores it to glycine and benzoic acid.
Extensive information about the biochemistry of hippuric acid and its implications for human health can be found in the ScienceDirect entry on the compound.
1. CAS Reg. No. 77-95-2.
The Uses of Hippuric acid
N-Benzoylglycine also known as Hippuric Acid is the glycine conjugate of benzoic acid commonly found in ruminant urine. It is synthesized in the liver and its production is greatly increased following consuption of benzoic acid. In itself it does not have a direct biological function, however p-hydroxy-hippurica acid can be used as an inhibitor of Ca2+ ATPase.
Properties of Hippuric acid
Melting point: | 187-191 °C (lit.) |
Boiling point: | 311.69°C (rough estimate) |
Density | 1,371 g/cm3 |
storage temp. | Store below +30°C. |
solubility | 3.26g/l |
form | Crystalline Powder |
appearance | white crystals or powder |
color | White to almost white |
Water Solubility | Soluble in water. |
Safety information for Hippuric acid
Signal word | Danger |
Pictogram(s) |
Corrosion Corrosives GHS05 Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H302:Acute toxicity,oral H315:Skin corrosion/irritation H318:Serious eye damage/eye irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation |
Precautionary Statement Codes |
P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P280:Wear protective gloves/protective clothing/eye protection/face protection. P304+P340:IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. P405:Store locked up. |
Computed Descriptors for Hippuric acid
InChIKey | QIAFMBKCNZACKA-UHFFFAOYSA-N |
Abamectin manufacturer
NSR Laboratories Pvt. Ltd.
AMINO ORGANICS
Aditya Chemicals
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