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Shikimic Acid
Ingredient for Production of Oseltamivir
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printable Application Sheet
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Notes: Shikimic acid is a key ingredient in the production of Tamiflu®, an antiviral drug for Influenza virus A and swine-origin influenza
(H1N1). Shikimic acid can be found in the leaves and organs of many plants. This carboxylic acid is also an essential compound in metabolic
pathways for aromatic amino acids and alkaloids in plants. Moreover, shikimic acid comes from grape skin and is always present in wines.
Determination of its concentration in wine can be used as a tool to differentiate between different red wine varieties.
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Method Conditions
| Column |
Cogent Diamond Hydride™, 4µm, 100A |
| Catalog No. |
70000-05P-2 |
| Dimensions |
2.1 x 50 mm |
| Solvents |
| A: | 50% methanol/ 50% DI water/ 10 mM amonium acetate |
| B: | 90% Acetonitrile/ 10% DI water/ 10 mM ammonium acetate |
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| Gradient |
| time (min.) |
%B |
time (min.) |
%B |
| 0 |
95 |
8 |
50 |
| 5 |
50 |
10 |
95 |
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| Injection Vol. |
1 microL |
| Flow rate |
0.4 mL/min. |
| Detection |
ESI - NEG - Agilent 6210 MSD TOF mass spectrometer |
| Sample |
Stock Solution: 0.1 mg/mL shikimic acid in methanol diluent.
Working solution: Stock was diluted using 50% solvent A and 50% solvent B mixture for the final concentration 1 mg/L. Before
injection, solution was filtered using a 0.45 micron nylon filter (MicroSolv Tech Corp). |
| Peak |
Shikimic acid 173.0455 m/z (M - H)- |
Discussion
The method shown in this application note assures both high specificity and high sensitivity for Shikimic Acid, a synthetic ingredient for the
production of the pharmaceutical Oseltamivir marketed as Tamiflu®. Using this LC-MS friendly ANP method allows for a 10-100 fold increase in
sensitivity over reversed phase methods. Also note that while using these columns, very little time is needed for equilibration between gradient runs.
One column volume is all that is required for peak precision.
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