Prephenic acid

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Prephenic acid
Names
Preferred IUPAC name
(1s,4s)-1-(2-Carboxy-2-oxoethyl)-4-hydroxycyclohexa-2,5-diene-1-carboxylic acid
Other names
Prephenate; cis-1-Carboxy-4-hydroxy-α-oxo-2,5-cyclohexadiene-1-propanoic acid
Identifiers
3D model (
JSmol
)
ChEBI
ChemSpider
MeSH Prephenic+acid
UNII
  • 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+ checkY
    Key: FPWMCUPFBRFMLH-XGAOUMNUSA-N checkY
  • 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
  • O=C(O)[C@@]/1(CC(=O)C(O)=O)\C=C/[C@@H](O)\C=C\1
Properties
C10H10O6
Molar mass 226.184 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 checkY☒N ?)

Prephenic acid, commonly also known by its

secondary metabolites of the shikimate
pathway.

It is biosynthesized by a [3,3]-

chorismate.[1][2]

Stereochemistry

Prephenic acid is an example of achiral (optically inactive) molecule which has two

chirotopic centers), the C1 and the C4 cyclohexadiene ring atoms. It has been shown[3] that of the two possible diastereoisomers, the natural prephenic acid is one that has both substituents at higher priority (according to CIP rules) on the two pseudoasymmetric carbons, i.e. the carboxyl and the hydroxyl groups, in the cis configuration, or (1s,4s) according to the new IUPAC stereochemistry rules (2013).[4]

The other stereoisomer, i.e. trans or, better, (1r,4r), is called epiprephenic.

See also

References

  1. PMID 100134
    .
  2. doi:10.1021/jp972501l.{{cite journal}}: CS1 maint: multiple names: authors list (link
    )
  3. ISSN 0002-7863
    .
  4. ISBN 9780854041824
    .
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