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Merck
CN

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

Key Documents

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Product Name

Shikimic acid, analytical standard

InChI key

JXOHGGNKMLTUBP-HSUXUTPPSA-N

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

SMILES string

O[C@@H]1CC(=C[C@@H](O)[C@H]1O)C(O)=O

grade

analytical standard

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

Quality Level

100

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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).

Other Notes

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

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

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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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
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
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
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
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