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69686

Shikimic acid

analytical standard

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
UNSPSC Code:
85151701
NACRES:
NA.24
PubChem Substance ID:
329761865
EC Number:
205-334-2
Beilstein/REAXYS Number:
2210055
MDL number:
MFCD00066278
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grade

analytical standard

Quality Level

100

assay

98.0-102.0% (T)

optical activity

[α]/D -180.0±5.0°, c = 4 in H2O

shelf life

limited shelf life, expiry date on the label

technique(s)

HPLC: suitable, gas chromatography (GC): suitable

mp

185-187 °C (lit.)

application(s)

food and beverages

format

neat

storage temp.

2-8°C

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 reference standard in the separation and determination of the analyte in fronds of brown seaweed, Cystoseira tamariscifolia using ultra high-performance liquid chromatography with ultraviolet detection (UHPLC-UV).
Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Other Notes

This compound is commonly found in plants of the genus: ginkgo

pictograms

Corrosion
GHS05

signalword

Danger

hcodes

H318

Hazard Classifications

Eye Dam. 1

Storage Class

11 - Combustible Solids

wgk

WGK 3

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Certificates of Analysis (COA)

Lot/Batch Number
BCCN7938
BCCM0235
BCCL1294
BCCG9838
BCCC7004

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Chloé Lemaître et al.
Journal of bacteriology, 196(7), 1343-1349 (2014-01-21)
The ability to capture iron is a challenge for most bacteria. The neonatal meningitis Escherichia coli strain S88 possesses several iron uptake systems, notably including siderophores. Transcriptional analysis of the ColV plasmid pS88 has shown strong induction of a previously
Varun Rawat et al.
Organic & biomolecular chemistry, 10(20), 3988-3990 (2012-04-24)
A new enantioselective synthesis of the anti-influenza agent (-)-oseltamivir free base (7.1% overall yield; 98% ee) and (-)-methyl 3-epi-shikimate (16% overall yield; 98% ee) has been described from readily available raw materials. Sharpless asymmetric epoxidation and diastereoselective Barbier allylation of
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
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
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
View All Related Papers

Global Trade Item Number

SKUGTIN
69686-50MG04061832785653

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