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Encyclopedia Britannica



HIPPURIC ACID (Gr. iazros, horse, ovpov, urine)

This article appears in Volume V13, Page 523 of the Encyclopedia Britannica.

Encyclopedia Britannica - Main :: HIG-HOR
HIPPURIC ACID (Gr. iazros, horse, ovpov, urine) , benzoyl glycocoll or benzoyl amidoacetic acid, C9H9NO3 or C6H5CO NHCH2CO2H, an organic acid found in the urine of horses and other herbivorae. It is excreted when many aromatic compounds, such as benzoic acid and
toluene
 , are taken internally. J. v.
Liebig
  in 1829 showed that it differed from benzoic acid, and in 1839 determined its constitution, while in 18J3 V. Dessaignes (Ann. 87, p. 325) synthesized it by acting with benzoyl chloride on
zinc
  glycocollide. It is also formed by
heating
  benzoic anhydride with glycocoll (Th.
Curtius
 , Ber., 1884, 17, p. 1662), and by
heating
  benzamide with monochloracetic acid. It crystallizes in rhombic prisms which are readily soluble in hot
water
 , melt at 187 C. and decompose at about 2400 C. It is readily hydrolysed by hot
caustic
  alkalis to benzoic acid and glycocoll. Nitrous acid converts it into benzoyl glycollic acid, C6H,CO.OCH2CO2H. Its
ethyl
  ester reacts with hydrazine to form hippuryl hydrazine, C6H5CONHCH2CONHNH2, which was used by
Curtius
  for the preparation of azoimide (q.v.).


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