Shikimic acid

Shikimic acid
Chemical structure of shikimic acid	3D model of shikimic acid
Names
	Preferred IUPAC name (3R,4S,5R)-3,4,5-Trihydroxycyclohex-1-ene-1-carboxylic acid
Identifiers
CAS Number	138-59-0 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:16119 ;
ChEMBL	ChEMBL290345 ;
ChemSpider	8412 ;
ECHA InfoCard	100.004.850
EC Number	205-334-2;
KEGG	C00493 ;
PubChem CID	8742;
UNII	29MS2WI2NU ;
CompTox Dashboard (EPA)	DTXSID4032039 ;
	InChI InChI=1S/C7H10O5/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1,4-6,8-10H,2H2,(H,11,12)/t4-,5-,6-/m1/s1 Key: JXOHGGNKMLTUBP-HSUXUTPPSA-N ; InChI=1/C7H10O5/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1,4-6,8-10H,2H2,(H,11,12)/t4-,5-,6-/m1/s1/f/h11H; InChI=1/C7H10O5/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1,4-6,8-10H,2H2,(H,11,12)/t4-,5-,6-/m1/s1 Key: JXOHGGNKMLTUBP-HSUXUTPPBZ;
	SMILES C1[C@H]([C@@H]([C@@H](C=C1C(=O)O)O)O)O;
Properties
Chemical formula	C7H10O5
Molar mass	174.15 g/mol
Melting point	185 to 187 °C (365 to 369 °F; 458 to 460 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Shikimic acid, more commonly known as its anionic form shikimate, is a cyclohexene, a cyclitol and a cyclohexanecarboxylic acid. It is an important biochemical metabolite in plants and microorganisms. Its name comes from the Japanese flower shikimi (シキミ, the Japanese star anise, Illicium anisatum), from which it was first isolated in 1885 by Johan Fredrik Eykman.^[1] The elucidation of its structure was made nearly 50 years later.^[2]

^ Eykman, J. F. (1881). "The botanical relations of Illicium religiosum Sieb., Illicium anisatum Lour". American Journal of Pharmacy. 53 (8).
^ Enrich, Liza B.; Scheuermann, Margaret L.; Mohadjer, Ashley; Matthias, Kathryn R.; Eller, Chrystal F.; Newman, M. Scott; Fujinaka, Michael; Poon, Thomas (April 2008). "Liquidambar styraciflua: a renewable source of shikimic acid". Tetrahedron Letters. 49 (16): 2503–2505. doi:10.1016/j.tetlet.2008.02.140.

[1] Eykman, J. F. (1881). "The botanical relations of Illicium religiosum Sieb., Illicium anisatum Lour". American Journal of Pharmacy. 53 (8).

[Enrich-2] Enrich, Liza B.; Scheuermann, Margaret L.; Mohadjer, Ashley; Matthias, Kathryn R.; Eller, Chrystal F.; Newman, M. Scott; Fujinaka, Michael; Poon, Thomas (April 2008). "Liquidambar styraciflua: a renewable source of shikimic acid". Tetrahedron Letters. 49 (16): 2503–2505. doi:10.1016/j.tetlet.2008.02.140.

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