Chorismic acid

Chorismic acid
Names
	IUPAC name (3R,4R)-3-[(1-carboxyvinyl)oxy]-4-hydroxycyclohexa-1,5-diene-1-carboxylic acid
Identifiers
CAS Number	617-12-9;
3D model (JSmol)	Interactive image;
ChemSpider	11542;
ECHA InfoCard	100.164.204
CompTox Dashboard (EPA)	DTXSID50210697 ;
	InChI InChI=1/C10H10O6/c1-5(9(12)13)16-8-4-6(10(14)15)2-3-7(8)11/h2-4,7-8,11H,1H2,(H,12,13)(H,14,15)/t7-,8-/m1/s1 Key: WTFXTQVDAKGDEY-HTQZYQBOBD;
	SMILES O=C(O)C1=C/[C@@H](O/C(C(=O)O)=C)[C@H](O)/C=C1;
Properties
Chemical formula	C10H10O6
Molar mass	226.18 g/mol
Melting point	140 °C
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Chorismic acid, more commonly known as its anionic form chorismate, is an important biochemical intermediate in plants and microorganisms. It is a precursor for:

The aromatic amino acids phenylalanine and tyrosine
Indole, indole derivatives and tryptophan
2,3-dihydroxybenzoic acid (DHB) used for enterobactin biosynthesis
The plant hormone salicylic acid^[1]
Many alkaloids and other aromatic metabolites.

The name chorismic acid derives from a classical greek word, χωρίζω meaning "to separate",^[2] because the compound plays a role as a branch-point in aromatic amino acid biosynthesis.^[3]

Biosynthesis

Shikimate → shikimate-3-phosphate → 5-enolpyruvylshikimate-3-phosphate → chorismate.

External links

Shikimate and chorismate biosynthesis

References

^ Wildermuth MC, Dewdney J, Wu G, Ausubel FM (2001). "Isochorismate synthase is required to synthesize salicylic acid for plant defence". Nature. 414 (6863): 562–5. doi:10.1038/35107108. PMID 11734859.{{cite journal}}: CS1 maint: multiple names: authors list (link)
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[1] Wildermuth MC, Dewdney J, Wu G, Ausubel FM (2001). "Isochorismate synthase is required to synthesize salicylic acid for plant defence". Nature. 414 (6863): 562–5. doi:10.1038/35107108. PMID 11734859.{{cite journal}}: CS1 maint: multiple names: authors list (link)

[2] . ISBN 0-19-864226-1. {{cite book}}: Cite uses deprecated parameter |authors= (help); Missing or empty |title= (help); Unknown parameter |name= ignored (help)

[3] Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi:10.1016/S0968-0004(98)01330-9, please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with |doi=10.1016/S0968-0004(98)01330-9 instead.

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