Hippuric acid

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Structural formula
Structural formula of hippuric acid
General
Surname Hippuric acid
other names
  • Benzamidoacetic acid
  • Benzoylaminoacetic acid
  • N -Benzoylglycine
  • Acidum hippuricum ( Latin )
Molecular formula C 9 H 9 NO 3
Brief description

colorless and odorless solid

External identifiers / databases
CAS number 495-69-2
EC number 207-806-3
ECHA InfoCard 100.007.098
PubChem 464
ChemSpider 451
Wikidata Q412803
properties
Molar mass 179.18 g mol −1
Physical state

firmly

density

1.37 g cm −3

Melting point

187-191 ° C

solubility
safety instructions
GHS labeling of hazardous substances
07 - Warning

Caution

H and P phrases H: 302-315-318-335
P: 301 + 330 + 331-302 + 352-305 + 351 + 338
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Hippuric acid is an organic carboxylic acid . The name of the compound is derived from its occurrence in the urine of horses (gr. Hippos ). Biochemically, hippuric acid can arise from glycine and the benzoic acid contained in some fruits .

Biological importance

Hippuric acid is used to detoxify benzoic acid and is mainly synthesized in the kidneys , especially of herbivorous mammals (e.g. horses, cattle, sheep) using ATP and coenzyme A from the amino acids glycine and benzoic acid. To a lesser extent, hippuric acid is also found in the urine of carnivorous or omnivorous mammals (e.g. dogs, pigs, humans) and in the urine of herbivorous mussels. The ability to synthesize hippuric acid was demonstrated in the larvae of the mosquito Aedes aegypti . Since there is insufficient glycine in birds, benzoic acid is detoxified by binding to the amino acid ornithine , resulting in the excretion product ornithuric acid .

Hippuric acid has a bacteria-killing effect in the urine, so that a high concentration can promote healing in urinary tract infections. However, it is also associated with rheumatic symptoms, as the substance is poorly soluble in water and can therefore only be excreted slowly in the event of overproduction (in the liver after consumption of fruits containing benzoic acid).

Extraction and presentation

Hippuric acid is prepared using a Schotten-Baumann reaction in which glycine and benzoyl chloride are converted in an alkaline medium.

Gross reaction equation

Due to the greater electronegativity of the substituents, the carbon atom of the carbonyl group has a partial positive charge, which means that the free electron pair of the amino group can attack as a nucleophile in an addition-elimination reaction and the chlorine atom is split off. The free proton of the amino group is captured in an alkaline solution. If the solution is acidified, hippuric acid precipitates as a product.

Analytics

For a reliable qualitative and quantitative determination of hippuric acid can after adequate sample preparation the gas chromatography after derivatization or HPLC and coupled to the mass spectrometry are used. These methods are also used for the analysis of dried urine samples collected on filter paper. These methods are also suitable for determining the effect of tea consumption on the hippuric acid level.

Derivatives

p -Aminohippuric acid (PAH) is a derivative of hippuric acid which is used in medicine to test kidney function ( PAH clearance ).

Individual evidence

  1. ↑ a b c Entry on hippuric acid. In: Römpp Online . Georg Thieme Verlag, accessed on December 28, 2014.
  2. ↑ a b c data sheet Hippuric acid, 98% from AlfaAesar, accessed on December 6, 2019 ( PDF )(JavaScript required) .
  3. ↑ Data sheet hippuric acid from Sigma-Aldrich , accessed on October 9, 2016 ( PDF ).Template: Sigma-Aldrich / name not given
  4. ↑ Data sheet hippuric acid (PDF) from Merck , accessed on December 26, 2019.
  5. ^ Heinz Penzlin: Textbook of Animal Physiology. 5th edition. Gustav Fischer Verlag, Jena 1991, ISBN 3-334-60363-6 .
  6. ↑ P. Kongtip, J. Vararussami, V. Pruktharathikul: Modified method for determination of hippuric acid and methylhippuric acid in urine by gas chromatography. In: J Chromatogr B Biomed Sci Appl. 10, 751 (1), Feb 2001, pp. 199-203. PMID 11232852
  7. ↑ D. Remane, S. Grunwald, H. Hoeke, A. Mueller, S. Roeder, M. von Bergen, DK Wissenbach: Validation of a multi-analyte HPLC-DAD method for determination of uric acid, creatinine, homovanillic acid, niacinamide, hippuric acid, indole-3-acetic acid and 2-methylhippuric acid in human urine. In: J Chromatogr B Analyt Technol Biomed Life Sci. 998-999, Aug 15, 2015, pp. 40-44. PMID 26151191
  8. ↑ S. Marchese, R. Curini, A. Gentili, D. Perret, LM Rocca: Simultaneous determination of the urinary metabolites of benzene, toluene, xylene and styrene using high-performance liquid chromatography / hybrid quadrupole time-of-flight mass spectrometry . In: Rapid Commun Mass Spectrom. 18 (3), 2004, pp. 265-272. PMID 14755610
  9. ↑ MV Antunes, CG Niederauer, R. Linden: Development, validation and clinical evaluation of a dried urine spot method for determination of hippuric acid and creatinine. In: Clin Biochem. 46 (13-14), Sep 2013, pp. 1276-1280. PMID 23868019
  10. ↑ SM Henning, P. Wang, N. Abgaryan, R. Vicinanza, DM de Oliveira, Y. Zhang, RP Lee, CL Carpenter, WJ Aronson, D. Heber: Phenolic acid concentrations in plasma and urine from men consuming green or black tea and potential chemopreventive properties for colon cancer. In: Mol Nutr Food Res. 57 (3), Mar 2013, pp. 483-493. PMID 23319439

Web links

Wiktionary: Hippuric acid  - explanations of meanings, word origins, synonyms, translations