Shikimic

Shikimic acid, often simply called shikimic, is a naturally occurring cyclohexene carboxylic acid. It is an essential intermediate in the shikimate pathway, a fundamental route in plants, bacteria, and fungi for the biosynthesis of the aromatic amino acids phenylalanine, tyrosine, and tryptophan. Humans and other animals lack this pathway, making shikimic acid and related metabolites nonessential in human metabolism but important for microbial and plant metabolism.

Natural occurrence and production: Shikimic acid is most famously abundant in the seeds of star anise (Illicium verum), and it is the primary commercial source. It can also be obtained from other plants and produced by microbial fermentation using engineered strains, offering alternative supply chains.

Chemical properties and applications: The molecule features a cyclohexene ring bearing three hydroxyl groups and a carboxyl function, making it a versatile chiral building block for organic synthesis. It serves as a starting material for the production of various aromatic compounds and derivatives, including pharmaceuticals.

Major uses in medicine: Shikimic acid is best known as a key precursor in the synthesis of oseltamivir (Tamiflu), an antiviral drug used to treat influenza. Production routes include chemical transformations of shikimic acid to intermediates used in the drug's final assembly, with continued research into improving supply and alternative routes.