Back حمض الهيبوريك Arabic هیپوریک اسید AZB Гіпуравая кіслата BE Kyselina hippurová Czech Hippursäure German Ιππουρικό οξύ Greek Ácido hipúrico Spanish هیپوریک اسید FA Hippurihappo Finnish Acide hippurique French

Hippuric acid

Hippuric acid
Structural formula of hippuric acid
Recrystallised hippuric acid
Names
IUPAC name
N-Benzoylglycine
Preferred IUPAC name
Benzamidoacetic acid
Other names
  • Hippuric acid
  • Benzoyl glycocoll
  • Benzoyl amidoacetic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.007.098 Edit this at Wikidata
KEGG
UNII
  • 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) checkY
    Key: QIAFMBKCNZACKA-UHFFFAOYSA-N checkY
  • InChI=1/C9H9NO3/c11-8(12)6-10-9(13)7-4-2-1-3-5-7/h1-5H,6H2,(H,10,13)(H,11,12)
    Key: QIAFMBKCNZACKA-UHFFFAOYAD
  • OC(=O)CNC(=O)c1ccccc1
Properties
C9H9NO3
Molar mass 179.175 g·mol−1
Density 1.371 g/cm3
Melting point 187 to 188 °C (369 to 370 °F; 460 to 461 K)
Boiling point 240 °C (464 °F; 513 K) (decomposes)
Hazards
Safety data sheet (SDS) Material Safety Data Sheet
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Hippuric acid (Gr. hippos, horse, ouron, urine) is a carboxylic acid and organic compound. It is found in urine and is formed from the combination of benzoic acid and glycine. Levels of hippuric acid rise with the consumption of phenolic compounds (such as in fruit juice, tea and wine). The phenols are first converted to benzoic acid, and then to hippuric acid and excreted in urine.[1]

Hippuric acid crystallizes in rhombic prisms which are readily soluble in hot water, melt at 187 °C, and decompose at about 240 °C.[2] High concentrations of hippuric acid may also indicate a toluene intoxication; however, scientists have called this correlation into question because there are other variables that affect levels of hippuric acid.[3] When many aromatic compounds such as benzoic acid and toluene are taken internally, they are converted to hippuric acid by reaction with the amino acid, glycine.

  1. ^ Wishart, David S.; Guo, An Chi; Oler, Eponine; Wang, Fel; Anjum, Afia; Peters, Harrison; Dizon, Raynard; Sayeeda, Zinat; Tian, Siyang; Lee, Brian L.; Berjanskii, Mark; Mah, Robert; Yamamoto, Mai; Jovel Castillo, Juan; Torres Calzada, Claudia; Hiebert Giesbrecht, Mickel; Lui, Vicki W.; Varshavi, Dorna; Varshavi, Dorsa; Allen, Dana; Arndt, David; Khetarpal, Nitya; Sivakumaran, Aadhavya; Harford, Karxena; Sanford, Selena; Yee, Kristen; Cao, Xuan; Budinsky, Zachary; Liigand, Jaanus; Zhang, Lun; Zheng, Jiamin; Mandal, Rupasri; Karu, Naama; Dambrova, Maija; Schiöth, Helgi B.; Gautam, Vasuk. "Showing metabocard for Hippuric acid (HMDB0000714)". Human Metabolome Database, HMDB. 5.0.
  2. ^ One or more of the preceding sentences incorporates text from a publication now in the public domain: Chisholm, Hugh, ed. (1911). "Hippuric Acid". Encyclopædia Britannica. Vol. 13 (11th ed.). Cambridge University Press. p. 523.
  3. ^ Pero, RW (2010). "Health consequences of catabolic synthesis of hippuric acid in humans". Current Clinical Pharmacology. 5 (1): 67–73. doi:10.2174/157488410790410588. PMID 19891605.

Hippuric acid

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