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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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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
BCCC7004
BCCC2964
BCBX0725
BCBV7313
BCBT7059

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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)
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
Garima Rawat et al.
Applied microbiology and biotechnology, 97(10), 4277-4287 (2013-04-05)
Shikimic acid is an industrially important chiral compound used as a key ingredient in formulation of drug Oseltamivir phosphate (Tamiflu) for the treatment of swine/avian flu. The high cost and limited availability of shikimic acid isolated from plants has detained
Saptarshi Ghosh et al.
Biotechnology advances, 30(6), 1425-1431 (2012-03-27)
Shikimic acid is a key intermediate for the synthesis of the antiviral drug oseltamivir (Tamiflu®). Shikimic acid can be produced via chemical synthesis, microbial fermentation and extraction from certain plants. An alternative production route is via biotransformation of the more
Hiroshi Maeda et al.
Annual review of plant biology, 63, 73-105 (2012-05-05)
L-tryptophan, L-phenylalanine, and L-tyrosine are aromatic amino acids (AAAs) that are used for the synthesis of proteins and that in plants also serve as precursors of numerous natural products, such as pigments, alkaloids, hormones, and cell wall components. All three
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