Shikimic acid Illicium verum Hook.f.Extract
CAS No. Registry Number:138-59-0 Shikimic acid
is a white crystalline compound of nonnitrogenous acid found in various
plants naturally. It has two kind functional groups in the same
molecule, three hydroxyl groups and a carboxylic acid group, which are
optically active. They can yield various kinds of esters and salts.
Shikimic acid is a cyclitol, a polyhydroxylated cycloalkane containing
at least three hydroxy groups in the ring at different positions.
Examples are inositol and quinic acid. The most important feature of
cyclitol is that there are chiral isomers, key intermediates in the
biosynthesis of aromatic compounds in living metabolism. Shikimic acid
is a key intermediate in the biochemical pathway from phosphoenolpyruvic
acid to tyrosine.
D-Erythrose-4-phosphate +
Phosphoenoylpyruvate ¢®©¡ 7-Phospho-2-dehydro-3-deoxy-
D-arabinoheptulosonate ¢®©¡ 3-Dehydroquinate ¢®©¡ 3-Dehydroshikimate
¢®©¡ Shikimate ¢®©¡ 3-Phosphoshikimate ¢®©¡
3-Phospho-5-enoylpyruvylshikimate ¢®©¡ Chorismate ¢®©¡ Prephenate ¢®©¡
Phenylpyruvate (or p-Hydroxyphenylpyruvate) ¢®©¡ L-Phenylalanine (or
L-Tyrosine)
Shikimic
acid is a precursor of many alkaloids, aromatic amino acids, and indole
derivatives. Shikimic acid is widely used as a chiral building block for
the synthesis of pharmaceuticals. An example of end product is an
antiviral drug oseltamivir, a neuraminidase inhibitor used in the
treatment and prophylaxis of both influenza A and influenza B.
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