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S5375

Sigma-Aldrich

Shikimic acid

≥99%, suitable for ligand binding assays

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C7H10O5
Número de CAS:
138-59-0
Peso molecular:
174.15
Beilstein/REAXYS Number:
2210055
EC Number:
205-334-2
MDL number:
MFCD00066278
UNSPSC Code:
12352106
PubChem Substance ID:
24899647
NACRES:
NA.25

product name

Shikimic acid, ≥99%

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

signalword

Danger

hcodes

H318

Hazard Classifications

Eye Dam. 1

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

ppe

Eyeshields, Gloves, type N95 (US)

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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USP

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D-Sorbitol ≥98% (GC)

Sigma-Aldrich

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L-Gulonic acid γ-lactone 95%

Sigma-Aldrich

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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)
Kai Chen et al.
Bioresource technology, 119, 141-147 (2012-06-26)
Shikimic acid (SA) is an important metabolic intermediate with diverse commercial applications. In this work, antisense RNA interference and gene deletion were carried out to inactivate the aroK gene in an SA-producing Escherichia coli strain, DHPYA-T7. In this strain, the
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
Glyphosate inhibition of ferric reductase activity in iron deficient sunflower roots.
Ozturk L
The New phytologist, 177(4), 899-906 (2008)
Inhibitory effects of shikimic acid on platelet aggragation and blood coagulation.
Ma Yi
Acta Pharmaceutica Sinica. B, 35, 1-3 (2000)
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