Shikimic acid
IUPAC name	(3R,4S,5R)-3,4,5-Trihydroxy- 1-cyclohexenecarboxylic acid
Identifiers
CAS number	[138-59-0]
EINECS number	205-334-2
InChI	1/C7H10O5/c8-4- 1-3(7(11)12)2-5(9)6(4) 10/h1,4-6,8-10H,2H2, (H,11,12)/t4-,5-,6- /m1/s1/f/h11H
Properties
Molecular formula	C7H10O5
Molar mass	174. IUPAC Nomenclature is a system of naming Chemical compounds and of describing the science of Chemistry in general CAS registry numbers are unique numerical identifiers for Chemical compounds Polymers biological sequences mixtures and Alloys They are also referred to The EINECS number (for European Inventory of Existing Chemical Substances) is a registry number given to each Chemical substance commercially available in the The IUPAC International Chemical Identifier ( InChI, pronounced "INchee" is a textual Identifier for Chemical substances designed to provide a A chemical formula is a way of expressing information about the Atoms that constitute a particular Chemical compound, and how the relationship between those atoms changes Molar mass, symbol M, is the Mass of one mole of a substance ( Chemical element or Chemical compound) 15 g/mol
Melting point	185–187 °C
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Shikimic acid, more commonly known as its anionic form shikimate, is an important biochemical intermediate in plants and microorganisms. The melting point of a solid is the temperature range at which it changes state from solid to Liquid. In Chemistry, the standard state of a material is its state at 1 bar (100 Kilopascals exactly An ion is an Atom or Molecule which has lost or gained one or more Valence electrons giving it a positive or negative electrical charge Its name comes from the Japanese flower shikimi (シキミ, Illicium anisatum), from which it was first isolated. For a topic outline on this subject see List of basic Japan topics. The Japanese star anise ( Illicium anisatum) is a tree similar to Chinese star anise.

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. Aromatic amino acids are Amino acids which include an aromatic ring In Chemistry, an amino acid is a Molecule containing both Amine and Carboxyl Functional groups In Biochemistry, this Phe redirects here For the BitTorrent feature see PHE. For the constellation see Phoenix (constellation. Tyrosine (abbreviated as Tyr or Y) or 4-hydroxyphenylalanine, is one of the 20 Amino acids that are used by cells to synthesize Indole is an Aromatic heterocyclic Organic compound. It has a bicyclic structure consisting of a six-membered Benzene ring fused to a five-membered Aromatic amino acids are Amino acids which include an aromatic ring In Chemistry, an amino acid is a Molecule containing both Amine and Carboxyl Functional groups In Biochemistry, this Tryptophan (abbreviated as Trp or W) is one of the 20 standard amino acids, as well as an Essential amino acid in the Human diet This article is about the chemical compounds alkaloids For the Pharmaceutical company in the Republic of Macedonia see Alkaloid (company. Metabolomics is the "systematic study of the unique chemical fingerprints that specific cellular processes leave behind" - specifically the study of their small-molecule metabolite Tannins are Astringent, bitter plant Polyphenols that either bind and Precipitate or shrink Proteins The astringency from the tannins is what The term flavonoid (or bioflavonoid refers to a class of Plant Secondary metabolites According to the IUPAC nomenclature they can be classified into Lignin or lignen is a complex Chemical compound most commonly derived from Wood and an integral part of the secondary Cell walls of Plants

In the pharmaceutical industry, shikimic acid from the Chinese star anise is used as a base material for production of Tamiflu (oseltamivir). ( See also Illicium floridanum which is known as Chakra Phool (Badian in India and Star anise in the Eastern USA Oseltamivir ( INN) (ɒsəlˈtæmɨvɪr is an Antiviral drug that is used in the treatment and Prophylaxis of both Influenzavirus A and Influenzavirus Although shikimic acid is present in most autotrophic organisms, it is a biosynthetic intermediate and generally found in very low concentrations. An autotroph (from the Greek autos = self and trophe = nutrition is an Organism that produces complex Organic compounds from simple The low isolation yield of shikimic acid from the Chinese star anise is blamed for the 2005 shortage of oseltamivir. Oseltamivir ( INN) (ɒsəlˈtæmɨvɪr is an Antiviral drug that is used in the treatment and Prophylaxis of both Influenzavirus A and Influenzavirus Shikimic acid can also be extracted from the seeds of the sweetgum fruit, which is abundant in North America, in yields of around 1. Sweetgum ( Liquidambar) is a genus of four species of Flowering plants in the family Altingiaceae, though formerly often treated in the Hamamelidaceae 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. ^[1]

Biosynthesis

Phosphoenolpyruvate and erythrose-4-phosphate react to form 3-deoxy-D-arabinoheptulosonate-7-phosphate (DAHP), in a reaction catalysed by the enzyme DAHP synthase. Phosphoenolpyruvate (synonyms phosphoenolpyruvic acid, PEP) is an important Chemical compound in Biochemistry. Erythrose 4-phosphate is an intermediate in the Pentose phosphate pathway. DAHP is then transformed to 3-dehydroquinate(DHQ), in a reaction catalysed by DHQ synthase. 3-Dehydroquinic acid (DHQ is the first carbocyclic intermediate of the Shikimate pathway Although this reaction requires NAD as a cofactor, the enzymic mechanism regenerates it, resulting in the net use of no NAD (note that diagram is incorrect).

Biosynthesis of 3-dehydroquinate from phopsphoenolpyruate and erythrose-4-phosphate

DHQ is dehydrated to 3-dehydroshikimate by the enzyme dehydroquinase, which is reduced by to shikimic acid by the enzyme shikimate dehydrogenase, which uses NADPH as a cofactor. Nicotinamide adenine dinucleotide phosphate ( NADP+, in older notation triphosphopyridine nucleotide TPN) is used in anabolic reactions such as Lipid

Biosynthesis of shikimic acid from 3-dehydroquinate

References

External links

• Shikimate and chorismate biosynthesis