Prephenic acid

Prephenic acid

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Names
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
Identifiers
CAS Number	126-49-8 (unspecified) N 87664-40-2 (cis) Y
ChEBI	CHEBI:84387 N
ChemSpider	16735981 Y
Jmol 3D model	Interactive image
MeSH	Prephenic+acid
PubChem	1028
InChI InChI=1S/C10H10O6/c11-6-1-3-10(4-2-6,9(15)16)5-7(12)8(13)14/h1-4,6,11H,5H2,(H,13,14)(H,15,16)/t6-,10+ Y Key: FPWMCUPFBRFMLH-XGAOUMNUSA-N Y InChI=1/C10H10O6/c11-6-1-3-10(4-2-6,9(15)16)5-7(12)8(13)14/h1-4,6,11H,5H2,(H,13,14)(H,15,16)/t6-,10+ Key: FPWMCUPFBRFMLH-XGAOUMNUBN
SMILES O=C(O)[C@@]/1(CC(=O)C(O)=O)\C=C/[C@@H](O)\C=C\1
Properties
Chemical formula	C10H10O6
Molar mass	226.18 g·mol−1
Vapor pressure	{{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
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.