S5375
Shikimic acid
≥99%, suitable for ligand binding assays
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All Photos(3)
Synonym(s):
(3R,4S,5R)-(−)-3,4,5-Trihydroxy-1-cyclohexenecarboxylic acid
Empirical Formula (Hill Notation):
C7H10O5
CAS Number:
Molecular Weight:
174.15
Beilstein:
2210055
EC Number:
MDL number:
UNSPSC Code:
12352106
PubChem Substance ID:
NACRES:
NA.25
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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
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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.
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Dam. 1
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)
Marco Krämer et al.
Metabolic engineering, 5(4), 277-283 (2003-12-04)
Shikimic acid is a high valued compound used as a key starting material for the synthesis of the neuramidase inhibitor GS4104, which was developed under the name Tamiflu for treatment of antiviral infections. An excellent alternative to the isolation of
Ruben Vanholme et al.
Science (New York, N.Y.), 341(6150), 1103-1106 (2013-08-21)
Lignin is a major component of plant secondary cell walls. Here we describe caffeoyl shikimate esterase (CSE) as an enzyme central to the lignin biosynthetic pathway. Arabidopsis thaliana cse mutants deposit less lignin than do wild-type plants, and the remaining
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
Glyphosate inhibition of ferric reductase activity in iron deficient sunflower roots.
Ozturk L
The New phytologist, 177(4), 899-906 (2008)
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