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Shikimic acid information


Shikimic acid
Chemical structure of shikimic acid
Chemical structure of shikimic acid
3D model of shikimic acid
3D model of shikimic acid
Names
Preferred IUPAC name
(3R,4S,5R)-3,4,5-Trihydroxycyclohex-1-ene-1-carboxylic acid
Identifiers
CAS Number
  • 138-59-0 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:16119 checkY
ChEMBL
  • ChEMBL290345 checkY
ChemSpider
  • 8412 checkY
ECHA InfoCard 100.004.850 Edit this at Wikidata
EC Number
  • 205-334-2
KEGG
  • C00493 ☒N
PubChem CID
  • 8742
UNII
  • 29MS2WI2NU ☒N
CompTox Dashboard (EPA)
  • DTXSID4032039 Edit this at Wikidata
InChI
  • InChI=1S/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 checkY
    Key: JXOHGGNKMLTUBP-HSUXUTPPSA-N checkY
  • 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
  • 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
    Key: JXOHGGNKMLTUBP-HSUXUTPPBZ
SMILES
  • C1[C@H]([C@@H]([C@@H](C=C1C(=O)O)O)O)O
Properties
Chemical formula
C7H10O5
Molar mass 174.15 g/mol
Melting point 185 to 187 °C (365 to 369 °F; 458 to 460 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Shikimic acid, more commonly known as its anionic form shikimate, is a cyclohexene, a cyclitol and a cyclohexanecarboxylic acid. It is an important biochemical metabolite in plants and microorganisms. Its name comes from the Japanese flower shikimi (シキミ, the Japanese star anise, Illicium anisatum), from which it was first isolated in 1885 by Johan Fredrik Eykman.[1] The elucidation of its structure was made nearly 50 years later.[2]

  1. ^ Eykman, J. F. (1881). "The botanical relations of Illicium religiosum Sieb., Illicium anisatum Lour". American Journal of Pharmacy. 53 (8).
  2. ^ Enrich, Liza B.; Scheuermann, Margaret L.; Mohadjer, Ashley; Matthias, Kathryn R.; Eller, Chrystal F.; Newman, M. Scott; Fujinaka, Michael; Poon, Thomas (April 2008). "Liquidambar styraciflua: a renewable source of shikimic acid". Tetrahedron Letters. 49 (16): 2503–2505. doi:10.1016/j.tetlet.2008.02.140.

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Shikimic acid

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Shikimic acid, more commonly known as its anionic form shikimate, is a cyclohexene, a cyclitol and a cyclohexanecarboxylic acid. It is an important biochemical...

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Shikimate pathway

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The shikimate pathway (shikimic acid pathway) is a seven-step metabolic pathway used by bacteria, archaea, fungi, algae, some protozoans, and plants for...

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Liquidambar styraciflua

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make chewing gum. L. styraciflua seeds may be a renewable source of shikimic acid. Traditionally, sweet gum has been used in Chinese medicine to treat...

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Illicium verum

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world's annual star anise crop to produce oseltamivir (Tamiflu) via shikimic acid. Illicium comes from the Latin illicio meaning "entice" or "seduce"...

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Cyclohexanecarboxylic acid

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acid include: abscisic acid buciclic acid chlorogenic acid chorismic acid dicyclomine quinic acid shikimic acid tranexamic acid Quinic acid Shikimic acid...

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Oseltamivir total synthesis

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name Tamiflu. Its commercial production starts from the biomolecule shikimic acid harvested from Chinese star anise and from recombinant E. coli. Control...

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Phenylpropanoid

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that are biosynthesized by plants from the amino acids phenylalanine and tyrosine in the shikimic acid pathway. Their name is derived from the six-carbon...

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Penicillium griseofulvum

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patulin, penifulvin A, cyclopiazonic acid, roquefortine C, shikimic acid, griseofulvin, and 6-Methylsalicylic acid (via a polyketide synthase). Penicillium...

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Rosavin

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the shikimic-chorismic acid pathway. Shikimic acid is made from the precursor compounds erythrose-4-phosphate, and phosphoenolpyruvate. Shikimic acid is...

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Caffeic acid

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hydroxylation produces the caffeic acid ester of shikimic acid, which converts to chlorogenic acid. It is the precursor to ferulic acid, coniferyl alcohol, and sinapyl...

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Oseltamivir

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discovered by scientists at Gilead Sciences using shikimic acid as a starting point for synthesis; shikimic acid was originally available only as an extract...

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Gallic acid

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supported by evidence. Benzoic acid Catechol Hydrolyzable tannin Pyrogallol Syringol Syringaldehyde Syringic acid Shikimic acid Haslam, E.; Cai, Y. (1994)...

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Fiddlehead

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are toxic. It is recommended to fully cook fiddleheads to destroy the shikimic acid. Ostrich fern (Matteuccia struthiopteris) is not thought to cause cancer...

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Fatty acid synthesis

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sugars to shikimic acid which is then converted to cyclohexylcarboxylic acid-CoA esters that serve as primers for omega-alicyclic fatty acid synthesis...

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Protecting group

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protecting groups may often shorten an enantioselective synthesis (e.g. shikimic acid for oseltamivir). As a rule, the introduction of a protecting group...

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Shilajit

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metabolites such as methyldiaminocyclohexane, shikimic acid, hippuric acid, quinic acid, hydroxyhippuric acid, and methyldiaminocyclohexane dimer. The composition...

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Cyclitol

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a response to salt or water stress. Some cyclitols (e.g. quinic or shikimic acid) are parts of hydrolysable tannins. Unsubstituted cyclitols with the...

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Syringic acid

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the shikimic acid pathway in plants. Syringic acid can be prepared by selectively hydrolyzing (demethylating) eudesmic acid with 20% sulfuric acid. Syringic...

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Aminoshikimic acid

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around a six-membered carbocyclic ring. Aminoshikimic acid is also an alternative to shikimic acid as a starting material for the synthesis of neuraminidase...

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Illicium anisatum

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the edible Chinese star anise and are used to identify its toxicity. Shikimic acid, a substance also present in Japanese star anise, is so-called after...

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Metabolism

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as antibiotics or industrial chemicals such as 1,3-propanediol and shikimic acid. These genetic modifications usually aim to reduce the amount of energy...

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IARC group 3

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compounds Semicarbazide hydrochloride Seneciphylline Senkirkine Sepiolite Shikimic acid Silica, amorphous Simazine Slag wool Sodium chlorite Sodium diethyldithiocarbamate...

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Amanita caesarea

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acid, ketoglutaric acid, fumaric acid, shikimic acid and traces of succinic acid were detected. Malic and ascorbic acids were the most abundant compounds...

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Cyanidin

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Phosphoenolpyruvic acid (PEP) and Erythrose 4-phosphate to form shikimic acid, which then further reacts to form specific aromatic amino acids. L-phenylalanine...

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Tryptophan

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proteins. Plants and microorganisms commonly synthesize tryptophan from shikimic acid or anthranilate: anthranilate condenses with phosphoribosylpyrophosphate...

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Crop desiccation

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(1980). "The herbicide glyphosate is a potent inhibitor of 5-enolpyruvyl-shikimic acid-3-phosphate synthase". Biochemical and Biophysical Research Communications...

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Smilax aristolochiifolia

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saponin, sarasaponin, sarsaparilloside, sarsaponin, sarsasapogenin, shikimic acid, sitosterol-d-glucoside, smilagenin, smilasaponin, smilax saponins A-C...

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Hydrolysable tannin

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quinic or shikimic acids). The hydroxyl groups of the carbohydrate are partially or totally esterified with phenolic groups such as gallic acid in gallotannins...

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