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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/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%

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

signalword

Danger

hcodes

H318

Hazard Classifications

Eye Dam. 1

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

ppe

Eyeshields, Gloves, type N95 (US)

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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Inhibitory effects of shikimic acid on platelet aggragation and blood coagulation.
Ma Yi
Acta Pharmaceutica Sinica. B, 35, 1-3 (2000)
Glyphosate inhibition of ferric reductase activity in iron deficient sunflower roots.
Ozturk L
The New phytologist, 177(4), 899-906 (2008)
Efficient elimination of nonstoichiometric enzyme inhibitors from HTS hit lists.
Habig M
Journal of Biomolecular Screening, 14(6), 679-689 (2009)
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
Garima Rawat et al.
Applied microbiology and biotechnology, 97(10), 4277-4287 (2013-04-05)
Shikimic acid is an industrially important chiral compound used as a key ingredient in formulation of drug Oseltamivir phosphate (Tamiflu) for the treatment of swine/avian flu. The high cost and limited availability of shikimic acid isolated from plants has detained
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