Shikimic acid is a naturally occurring molecule of crucial importance for numerous plant and microbial biosynthetic processes. It is central to the production of various biochemical compounds, some of which are essential for the industrial production of medications such as Tamiflu. This article offers a comprehensive exploration of shikimic acid, from its biosynthesis to its industrial applications, including cosmetics .
1. What is shikimic acid? (CAS: 138-59-0)
Shikimic acid is a naturally occurring organic molecule, more precisely a polyhydroxylated monoacid. It was first isolated from the Japanese shikimi flower by Johann Frederik Eijkmann in 1885. This discovery is the origin of the molecule's name. Shikimic acid is found in various autotrophic organisms, including star anise and Japanese star anise, although the isolation yield is relatively low.
Chemically, shikimic acid is an essential element in the biosynthesis of amino acids , such as phenylalanine, tyrosine, and tryptophan. These amino acids play a fundamental role in various metabolic processes and are precursors of many important metabolites, including tannins, lignin, and salicylic acid.
2. The role of shikimic acid in biosynthesis
2.1. Shikimate metabolic pathway
The shikimate pathway is a complex biochemical process that enables the synthesis of aromatic amino acids and other bioactive compounds in plants and microorganisms. This metabolic pathway begins with the reaction between phosphoenolpyruvate and erythrose-4-phosphate, leading to the formation of various intermediates, including 3-dehydroshikimate and shikimate itself.
Shikimate is then phosphorylated to produce 3-phosphoshikimate, which is involved in the synthesis of chorismic acid. Chorismic acid is a key intermediate in the formation of aromatic amino acids such as tyrosine and phenylalanine. This pathway is absent in animals, which explains its importance in microorganisms and plants.
2.2. Shikimic acid derivative metabolites
Shikimic acid is also the precursor of many important secondary metabolites. These include phenolic compounds such as gallic acid, resveratrol, tannins, and salicylic acid. These molecules play essential roles in plant defense against predators and diseases, as well as in growth and development processes.
In addition, shikimic acid participates in the biosynthesis of lignin, a major component of plant cell walls, which provides rigidity and protection to plant tissues.
3. Use of shikimic acid in the pharmaceutical industry
3.1. Shikimic acid and the production of oseltamivir (Tamiflu)
One of the best-known applications of shikimic acid is in the manufacture of oseltamivir, marketed as Tamiflu. This medication is used as an antiviral treatment for influenza infections. Shikimic acid is extracted primarily from star anise, a process that played a key role in the global response to influenza epidemics, particularly during the H1N1 influenza pandemic.
Extracting shikimic acid from natural sources, such as star anise, remains complex and expensive. Therefore, research is underway to produce this molecule using biotechnological methods, such as genetically modified Escherichia coli, to increase yield and reduce costs.
3.2. Applications in other areas of health
In addition to its role in the production of antivirals, shikimic acid possesses antioxidant and anti-inflammatory properties. These characteristics make it a promising candidate for the development of new drugs, particularly in the prevention of diseases related to aging and oxidative stress.
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4. Laboratory analysis and quantification of shikimic acid
4.1. Analytical techniques used
In industry and research laboratories, the analysis and quantification of shikimic acid are generally performed using chromatographic techniques such as HPLC (High-Performance Liquid Chromatography) coupled with UV detection. This method allows for the accurate identification and quantification of shikimic acid in various matrices, including plant extracts, food products, and cosmetics.
4.2. Laboratory process for the determination of shikimic acid
Laboratory analysis follows strict protocols to ensure reliable results. The process begins with sample collection, and the samples are stored in airtight containers to prevent contamination. The samples are then extracted and analyzed by HPLC-UV, a method known for its sensitivity and accuracy in detecting organic compounds.
4.3. Importance of matrix-based analysis
Shikimic acid is analyzed in various matrices depending on the application, whether it be dietary supplements, cosmetics, or pharmaceuticals. Each matrix requires adjustments to the analytical process to ensure accurate quantification that meets health standards.
5. The properties and benefits of shikimic acid
5.1. Chemical properties of shikimic acid
Shikimic acid is a cyclohexene carboxylic acid with three hydroxyl groups. It is essential in the formation of numerous aromatic compounds, contributing to aromagenesis in plants. Furthermore, its ability to form complex secondary metabolites gives it a key role in plant metabolism.
5.2. Health Benefits of Shikimic Acid
Shikimic acid possesses antioxidant and anti-inflammatory properties, making it an interesting ingredient for dietary supplements and personal care products. It is also being studied for its potential antiviral effects, in addition to its use in Tamiflu.
6. Precautions and toxicity of shikimic acid
6.1. Toxicity and side effects
Despite its many beneficial uses, shikimic acid can have toxic effects at high concentrations. While it is generally safe when used in pharmaceutical and cosmetic products at controlled doses, precautions should be taken to avoid overexposure.
6.2. Limitations of use in food and cosmetic products
The use of shikimic acid in food and cosmetic products is strictly regulated by international legislation. For example, in the European Union, concentration limits are imposed to ensure consumer safety.
7. Industrial applications and other uses of shikimic acid
7.1. Uses in the agrochemical and cosmetic industries
Shikimic acid is used as an ingredient in cosmetic products for its antioxidant properties. It is also used in the agrochemical industry for the formulation of certain plant protection products.
7.2. Its use as a herbicide target
Glyphosate, a widely used herbicide, inhibits the shikimate pathway in plants, preventing them from producing the aromatic amino acids essential for their growth. This action makes it an effective herbicide, although controversial due to its environmental effects.
Conclusion
Shikimic acid plays a crucial role in many biological and industrial processes. From its key function in the biosynthesis of aromatic amino acids to its applications in the manufacture of antivirals like Tamiflu, this natural molecule continues to demonstrate its importance in various sectors.
