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Shikimic acid can also be extracted from the seeds of the sweetgum (Liquidambar styraciflua) fruit, [2] which is abundant in North America, in yields of around 1.5%. For example, 4 kg (8.8 lb) of sweetgum seeds is needed for fourteen packages of Tamiflu. By comparison, star anise has been reported to yield 3% to 7% shikimic acid.
The current production method is based on the first scalable synthesis developed by Gilead Sciences [4] starting from naturally occurring quinic acid or shikimic acid.Due to lower yields and the extra steps required (because of the additional dehydration), the quinic acid route was dropped in favour of the one based on shikimic acid, which received further improvements by Hoffmann-La Roche.
Oseltamivir was discovered by scientists at Gilead Sciences using shikimic acid as a starting point for synthesis; shikimic acid was originally available only as an extract of Chinese star anise; but by 2006, 30% of the supply was manufactured recombinantly in E. coli. [65] [66] Gilead exclusively licensed their relevant patents to Roche in ...
Star anise oil is a highly fragrant oil used in cooking, perfumery, soaps, toothpastes, mouthwashes, and skin creams. Until 2012, when they switched to using genetically modified E. coli, Roche Pharmaceuticals used up to 90% of the world's annual star anise crop to produce oseltamivir (Tamiflu) via shikimic acid. [3]
Oseltamivir (also Tamiflu) is an oral antiviral drug against influenza (flu). It was the second inhibitor of the viral neuraminidase to be developed, after zanamivir, and the first to be taken as an oral tablet. It was originally synthesised from shikimic acid extracted from the star anise plant.
Aminoshikimic acid is an intriguing alternative to shikimic acid as a starting material for the synthesis of neuraminidase inhibitors such as the antiinfluenza agent oseltamivir. [3] Aminoshikimic acid is also a versatile chiral starting material for the synthesis of new pharmaceuticals.
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It is the major source of the chemical compound shikimic acid, a primary precursor in the pharmaceutical synthesis of anti-influenza drug oseltamivir (Tamiflu). [93] Inula helenium: Elecampane: It is used in herbal medicine as an expectorant and for water retention. [94]