Prephenic acid

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Prephenic acid
Prephenic acid.svg
IUPAC name
1-(2-Carboxy-2-oxoethyl)-4-hydroxycyclohexa-2,5-dienecarboxylic acid
Other names
Prephenate; cis-1-Carboxy-4-hydroxy-α-oxo-2,5-cyclohexadiene-1-propanoic acid
126-49-8 (unspecified) N
87664-40-2 (cis) YesY
ChemSpider 16735981 YesY
Jmol 3D model Interactive image
MeSH Prephenic+acid
PubChem 1028
Molar mass 226.18 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

Prephenic acid, commonly also known by its anionic form prephenate, is an intermediate in the biosynthesis of the aromatic amino acids phenylalanine and tyrosine.

It is synthesized by a [3,3]-sigmatropic Claisen rearrangement of chorismate.[1][2]

Prephenate biosynthesis.png


  1. ^ Helmut Goerisch (1978). "On the mechanism of the chorismate mutase reaction". Biochemistry. 17 (18): 3700. doi:10.1021/bi00611a004. 
  2. ^ Peter Kast, Yadu B. Tewari, Olaf Wiest, Donald Hilvert, Kendall N. Houk, and Robert N. Goldberg (1997). "Thermodynamics of the Conversion of Chorismate to Prephenate: Experimental Results and Theoretical Predictions". J. Phys. Chem. B. 101 (50): 10976–10982. doi:10.1021/jp972501l.