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Shikimic acid Illicium verum Hook.f.Extract |
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Additional_detail: 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 ¡æ 7-Phospho-
2-dehydro-3-deoxy- D-
arabinoheptulosonate ¡æ 3-
Dehydroquinate ¡æ 3-
Dehydroshikimate ¡æ Shikimate ¡æ
3-Phosphoshikimate ¡æ 3-Phospho-5-
enoylpyruvylshikimate ¡æ
Chorismate ¡æ Prephenate ¡æ
Phenylpyruvate (or p-
Hydroxyphenylpyruvate) ¡æ 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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