Shikimic acid

Names

IUPAC name

(3R,4S,5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid

Identifiers

CAS Number

138-59-0^Y

3D model (Jmol)

CHEBI:16119^Y

ChEMBL290345^Y

8412^Y

205-334-2

C00493^N

29MS2WI2NU^N

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^Y

Key: JXOHGGNKMLTUBP-HSUXUTPPSA-N^Y
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).

(what is ^YN ?)

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. The elucidation of its structure was made nearly 50 years later.

It appears in the list of Group 3 carcinogens of the International Agency for Research on Cancer. Group 3 means that the agent is not classifiable as to its carcinogenicity to humans. Nevertheless, it is recommended to roast tree fern fronds, a specialty called fiddlehead (furled fronds of a young tree fern in the order Cyatheales, harvested for use as a vegetable). These fronds are edible, but must be roasted first to remove shikimic acid.

Shikimic acid is also the glycoside part of some hydrolysable tannins. The acid is highly soluble in water and insoluble in nonpolar solvents, and this reflects on why shikimic acid is active only against gram-positive bacteria, due to outer membrane impermeability of gram-negatives.

Phosphoenolpyruvate and erythrose-4-phosphate react to form 3-deoxy-D-arabinoheptulosonate-7-phosphate (DAHP), in a reaction catalyzed by the enzyme DAHP synthase. DAHP is then transformed to 3-dehydroquinate (DHQ), in a reaction catalyzed by DHQ synthase. Although this reaction requires nicotinamide adenine dinucleotide (NAD) as a cofactor, the enzymic mechanism regenerates it, resulting in the net use of no NAD.

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