3-Dehydroshikimic acid

3-Dehydroshikimic acid is a chemical compound related to shikimic acid. 3-DHS is available in large quantity through engineering of the shikimic acid pathway.^[1]

3-Dehydroshikimic acid

Names
Preferred IUPAC name (4S,5R)-4,5-Dihydroxy-3-oxocyclohex-1-ene-1-carboxylic acid
Other names 3-Dehydroshikimate 3-DHS (−)-3-DHS
Identifiers
CAS Number	2922-42-1 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:30918 Y
ChemSpider	388830
ECHA InfoCard	100.162.474
PubChem CID	439774
InChI InChI=1S/C7H8O5/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1,5-6,9-10H,2H2,(H,11,12)/t5-,6-/m1/s1 Key: SLWWJZMPHJJOPH-PHDIDXHHSA-N InChI=1/C7H8O5/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1,5-6,9-10H,2H2,(H,11,12)/t5-,6-/m1/s1 Key: SLWWJZMPHJJOPH-PHDIDXHHBW
SMILES C1[C@H]([C@@H](C(=O)C=C1C(=O)O)O)O
Properties
Chemical formula	C7H8O5
Molar mass	172.136 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Metabolism

Biosynthesis: The enzyme 3-dehydroquinate dehydratase uses 3-dehydroquinate to produce 3-dehydroshikimate and H₂O.

3-Dehydroshikimate is then reduced to shikimic acid by the enzyme shikimate dehydrogenase, which uses nicotinamide adenine dinucleotide phosphate (NADPH) as a cofactor.

Biosynthesis of shikimic acid from 3-dehydroquinate

Gallic acid is also formed from 3-dehydroshikimate by the action of the enzyme shikimate dehydrogenase to produce 3,5-didehydroshikimate. This latter compound spontaneously rearranges to gallic acid.^[2][3][4]