MilliporeSigma
All Photos(3)

Documents

S5375

Sigma-Aldrich

Shikimic acid

≥99%

All Photos(3)
Synonym(s):
(3R,4S,5R)-(−)-3,4,5-Trihydroxy-1-cyclohexenecarboxylic acid
Empirical Formula (Hill Notation):
C7H10O5
CAS Number:
138-59-0
Molecular Weight:
174.15
Beilstein:
2210055
EC Number:
205-334-2
MDL number:
MFCD00066278
PubChem Substance ID:
24899647
NACRES:
NA.25

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

Looking for similar products? Visit Product Comparison Guide

Related Categories

Compare Similar Items

View Full Comparison

Show Differences

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
GHS05

Signal Word

Danger

Hazard Statements

H318

Precautionary Statements

P280 - P305 + P351 + P338

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)

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’.

Already Own This Product?

Documents related to the products that you have purchased in the past have been gathered in the Document Library for your convenience.

Visit the Document Library

Difficulty Finding Your Product Or Lot/Batch Number?

Product numbers are combined with Pack Sizes/Quantity when displayed on the website (example: T1503-25G). Please make sure you enter ONLY the product number in the Product Number field (Example: T1503).

Example:

T1503
Product Number
-
25G
Pack Size/Quantity

Additional examples:

705578-5MG-PW

PL860-CGA/SHF-1EA

MMYOMAG-74K-13

1000309185

enter as 1.000309185)

Having trouble? Feel free to contact Technical Service for assistance.

Lot and Batch Numbers can be found on a product's label following the words 'Lot' or 'Batch'.

Aldrich Products

  • For a lot number such as TO09019TO, enter it as 09019TO (without the first two letters 'TO').

  • For a lot number with a filling-code such as 05427ES-021, enter it as 05427ES (without the filling-code '-021').

  • For a lot number with a filling-code such as STBB0728K9, enter it as STBB0728 without the filling-code 'K9'.

Not Finding What You Are Looking For?

In some cases, a COA may not be available online. If your search was unable to find the COA you can request one.

Request COA

Customers Also Viewed

Slide 1 of 7

1 of 7

Chorismic acid barium salt from Enterobacter aerogenes ≥55%

Sigma-Aldrich

C1259

Chorismic acid barium salt from Enterobacter aerogenes

(-)-Quinic acid for resolution of racemates for synthesis

Sigma-Aldrich

8.00218

(-)-Quinic acid

Quinic Acid Pharmaceutical Secondary Standard; Certified Reference Material

Supelco

PHR1468

Quinic Acid

(−) Quinic acid analytical standard

Supelco

46944-U

(−) Quinic acid

Quinic acid United States Pharmacopeia (USP) Reference Standard

USP

1594506

Quinic acid

D-Sorbitol ≥98%

Sigma-Aldrich

S1876

D-Sorbitol

L-Gulonic acid γ-lactone 95%

Sigma-Aldrich

310301

L-Gulonic acid γ-lactone

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
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service