S5375
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:
Molecular Weight:
174.15
NACRES:
NA.25
PubChem Substance ID:
UNSPSC Code:
12352106
EC Number:
205-334-2
MDL number:
Beilstein/REAXYS Number:
2210055
Product Name
Shikimic acid, ≥99%
Quality Level
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
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.
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signalword
Danger
hcodes
Hazard Classifications
Eye Dam. 1
Storage Class
11 - Combustible Solids
wgk
WGK 3
ppe
Eyeshields, Gloves, type N95 (US)
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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)
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