MilliporeSigma
All Photos(3)

S5375

Sigma-Aldrich

Shikimic acid

≥99%

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:
PubChem Substance ID:
NACRES:
NA.25

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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1 of 4

This Item
696868.24476G1763
Shikimic acid ≥99%

Sigma-Aldrich

S5375

Shikimic acid

Shikimic acid analytical standard

Supelco

69686

Shikimic acid

(-)-Shikimic acid for synthesis

Sigma-Aldrich

8.24476

(-)-Shikimic acid

β-Glutamic acid

Sigma-Aldrich

G1763

β-Glutamic acid

form

powder

form

-

form

crystals

form

powder

technique(s)

ligand binding assay: suitable

technique(s)

HPLC: suitable, gas chromatography (GC): suitable

technique(s)

-

technique(s)

ligand binding assay: suitable

color

white to off-white

color

-

color

-

color

white to off-white

mp

185-187 °C (lit.)

mp

185-187 °C (lit.)

mp

190 °C

mp

-

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

Signal Word

Danger

Hazard Statements

Precautionary Statements

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)

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T1503
Product Number
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25G
Pack Size/Quantity

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705578-5MG-PW

PL860-CGA/SHF-1EA

MMYOMAG-74K-13

1000309185

enter as 1.000309185)

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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)
Efficient elimination of nonstoichiometric enzyme inhibitors from HTS hit lists.
Habig M
Journal of Biomolecular Screening, 14(6), 679-689 (2009)
Glyphosate inhibition of ferric reductase activity in iron deficient sunflower roots.
Ozturk L
The New phytologist, 177(4), 899-906 (2008)
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
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

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