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Shikimic acid

analytical standard

Synonyme(s) :

(3R,4S,5R)-(−)-3,4,5-Trihydroxy-1-cyclohexenecarboxylic acid

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About This Item

Formule empirique (notation de Hill):
C7H10O5
Numéro CAS:
138-59-0
Poids moléculaire :
174.15
Numéro Beilstein :
2210055
Numéro CE :
205-334-2
Numéro MDL:
MFCD00066278
Code UNSPSC :
85151701
ID de substance PubChem :
329761865
Nomenclature NACRES :
NA.24

Qualité

analytical standard

Niveau de qualité

100

Pureté

98.0-102.0% (T)

Activité optique

[α]/D -180.0±5.0°, c = 4 in H2O

Durée de conservation

limited shelf life, expiry date on the label

Technique(s)

HPLC: suitable
gas chromatography (GC): suitable

Pf

185-187 °C (lit.)

Application(s)

food and beverages

Format

neat

Température de stockage

2-8°C

Chaîne SMILES 

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

Clé InChI

JXOHGGNKMLTUBP-HSUXUTPPSA-N

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Catégories apparentées

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).

Conditionnement

Bottomless glass bottle. Contents are inside inserted fused cone.

Autres remarques

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

Pictogrammes

Corrosion
GHS05

Mention d'avertissement

Danger

Mentions de danger

H318

Conseils de prudence

P280 - P305 + P351 + P338

Classification des risques

Eye Dam. 1

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

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Certificats d'analyse (COA)

Lot/Batch Number
BCCM0235
BCCL1294
BCCG9838
BCCC7004
BCCC2964

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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
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)
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
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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