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69686

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Shikimic acid

analytical standard

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Synonym(s):
(3R,4S,5R)-(−)-3,4,5-Trihydroxy-1-cyclohexenecarboxylic acid
Empirical Formula (Hill Notation):
C7H10O5
CAS Number:
Molecular Weight:
174.15
Beilstein/REAXYS Number:
2210055
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.24

grade

analytical standard

Quality Level

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(s)

food and beverages

application(s)

-

application(s)

food and beverages

application(s)

food and beverages
forensics and toxicology
pharmaceutical
veterinary

format

neat

format

-

format

neat

format

neat

Quality Level

100

Quality Level

-

Quality Level

100

Quality Level

100

grade

analytical standard

grade

-

grade

analytical standard

grade

analytical standard

assay

98.0-102.0% (T)

assay

≥99%

assay

≥99.0% (HPLC)

assay

≥97.5% (HPLC)

Application

Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.
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).

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

pictograms

Corrosion

signalword

Danger

hcodes

Hazard Classifications

Eye Dam. 1

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3


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705578-5MG-PW

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1000309185

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Ecophysiological and metabolic responses to interactive exposure to nutrients and copper excess in the brown macroalga Cystoseira tamariscifolia.
Celis-Pla MSP, et al.
Marine Pollution Bulletin, 128, 214-222 (2018)
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
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
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

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