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S5375

Sigma-Aldrich

Shikimic acid

≥99%, suitable for ligand binding assays

Synonym(s):

(3R,4S,5R)-(−)-3,4,5-Trihydroxy-1-cyclohexenecarboxylic acid

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About This Item

Empirical Formula (Hill Notation):
C7H10O5
CAS Number:
138-59-0
Molecular Weight:
174.15
Beilstein:
2210055
EC Number:
205-334-2
MDL number:
MFCD00066278
UNSPSC Code:
12352106
PubChem Substance ID:
24899647
NACRES:
NA.25

product name

Shikimic acid, ≥99%

Quality Level

200

Assay

≥99%

form

powder

technique(s)

ligand binding assay: suitable

color

white to off-white

mp

185-187 °C (lit.)

SMILES string

O[C@@H]1CC(=C[C@@H](O)[C@H]1O)C(O)=O

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

InChI key

JXOHGGNKMLTUBP-HSUXUTPPSA-N

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Application

Shikimic acid has been used as a standard for the quantification of shikimate in apical parts of roots. It has also been used as a substrate in shikimate kinase assay.

Biochem/physiol Actions

Shikimic acid is observed to be carcinogenic in rat models, when administered. It serves as a precursor for the biosynthesis of aromatic amino acids, alkaloids and other aromatic metabolites in microorganisms. Shikimic acid is known to inhibit adenosine diphosphate (ADP) induced platelet aggregation and blood coagulation in rabbits.

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H318

Precautionary Statements

P280 - P305 + P351 + P338

Hazard Classifications

Eye Dam. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Efficient elimination of nonstoichiometric enzyme inhibitors from HTS hit lists.
Habig M
Journal of Biomolecular Screening, 14(6), 679-689 (2009)
Inhibitory effects of shikimic acid on platelet aggragation and blood coagulation.
Ma Yi
Acta Pharmaceutica Sinica. B, 35, 1-3 (2000)
Varun Rawat et al.
Organic & biomolecular chemistry, 10(20), 3988-3990 (2012-04-24)
A new enantioselective synthesis of the anti-influenza agent (-)-oseltamivir free base (7.1% overall yield; 98% ee) and (-)-methyl 3-epi-shikimate (16% overall yield; 98% ee) has been described from readily available raw materials. Sharpless asymmetric epoxidation and diastereoselective Barbier allylation of
Marco F Schmidt et al.
ChemMedChem, 8(1), 54-58 (2012-11-22)
Rational ligand design: Schaeffer's acid analogues were identified as novel inhibitors of M. tuberculosis type II dehydroquinase, a key enzyme of the shikimate pathway. Their likely binding mode was predicted using a combination of ensemble docking and flexible active site residues.
Amalia M Estévez et al.
Mini reviews in medicinal chemistry, 12(14), 1443-1454 (2012-07-26)
Shikimic acid, a natural compound is a key intermediate in the biosynthesis of amino acids. Consequently, this derivative is widely present in many plants and has interesting biological properties. But besides the pharmacological relevance of shikimic acid itself, it is
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