Shikimic acid CAS NO.138-59-0

Properties Molecular formula C7H10O5 Molar mass 174.15 g mol?1 Melting point 185–187 °C Shikimic acid, more commonly known as its anionic …

Properties Molecular formula C7H10O5 Molar mass 174.15 g mol?1 Melting point 185–187 °C Shikimic acid, more commonly known as its anionic form shikimate, is an important biochemical intermediate in plants and microorganisms. Its name comes from the Japanese flower shikimi (シキミ, Illicium anisatum), from which it was first isolated. Shikimic acid is a precursor for: the aromatic amino acids phenylalanine and tyrosine, indole, indole derivatives and aromatic amino acid tryptophan, many alkaloids and other aromatic metabolites, tannins, flavonoids, and lignin. In the pharmaceutical industry, shikimic acid from the Chinese star anise is used as a base material for production of Tamiflu (oseltamivir). Although shikimic acid is present in most autotrophic organisms, it is a biosynthetic intermediate and generally found in very low concentrations. The low isolation yield of shikimic acid from the Chinese star anise is blamed for the 2005 shortage of oseltamivir. Shikimic acid can also be extracted from the seeds of the sweetgum fruit, which is abundant in North America, in yields of around 1.5%, so just 4 kg of sweetgum seeds are enough for fourteen packages of Tamiflu. By comparison star anise has been reported to yield 3 to 7% shikimic acid. Recently biosynthetic pathways in E. coli have been enhanced to allow the organism to accumulate enough material to be used commercially