Shikimic Acid
product_name Shikimic Acid
CAS_number 138-59-0
formula C7H10O5
molar_mass 174.15 g/mol
pub_chem_CID 8742
drug_bank DB02262
chem_spider 8413
bioavailability Unknown
protein_binding Unknown
metabolism Unknown
elimination_halflife Unknown


FAQ

What is Shikimic Acid and where is it commonly found?

Shikimic Acid is a key biochemical intermediate in the shikimate pathway, which is crucial for the biosynthesis of aromatic amino acids in bacteria, fungi, algae, plants, and some microorganisms. This organic compound is ubiquitous in nature and is particularly prominent in many plant species. One of the most well-known sources of shikimic acid is the Chinese star anise (Illicium verum), from which it is often extracted for various applications. The acid itself appears as a white crystalline powder and plays an essential role in the metabolic processes of the organisms that produce it.

Plants such as pine trees, sweetgum fruit, and Gingko biloba are additional natural reservoirs from which shikimic acid can be derived. In terms of structural chemistry, shikimic acid is a cyclohexene, a type of cycloalkane, which contributes to its unique properties and efficacy in numerous applications. Its role in the shikimate pathway also links it directly to the production of many secondary metabolites, which can include essential oils and some types of antimicrobial agents.

Shikimic acid is pivotal in the field of biotechnology and pharmaceutical research. The importance of shikimic acid in drug synthesis, particularly as a precursor for producing antiviral medications such as Oseltamivir (Tamiflu), cannot be overstated. This critical role has spurred extensive research into its optimized extraction and synthetic production methods to meet global demand, especially during pandemic situations where large-scale antiviral manufacturing becomes essential.

How is Shikimic Acid used in the pharmaceutical industry?

In the pharmaceutical industry, shikimic acid is predominantly used as a starting material for the synthesis of Oseltamivir phosphate, commonly known by its brand name, Tamiflu. Oseltamivir is a crucial antiviral medication used in the treatment and prevention of influenza A and B. The drug functions by inhibiting the neuraminidase enzyme, thereby blocking the release of new virus particles and limiting the spread of infection within the respiratory tract.

Beyond its application in antiviral drugs, shikimic acid has shown promise in anti-inflammatory and antioxidant treatments. These therapeutic properties are rooted in the compound's ability to modulate the production of nitric oxide and other inflammatory mediators. Research is ongoing to explore the full spectrum of shikimic acid’s potential in managing chronic inflammatory diseases and oxidative stress-related conditions.

The extraction of shikimic acid from natural sources like star anise involves multiple steps to ensure purity and efficacy. This labor-intensive process underscores the importance of developing efficient synthetic pathways to produce shikimic acid on an industrial scale. Advances in microbial fermentation and genetic engineering have opened up new avenues for producing shikimic acid in more sustainable and cost-effective ways. These biotechnological innovations aim to meet the high demand for antiviral drugs, especially during flu outbreaks and pandemics.

Shikimic acid’s versatile chemical structure also makes it a valuable intermediate for synthesizing other pharmacologically active compounds. Its derivatives are being researched for their potential to act as antitumor agents and immunomodulators. Consequently, shikimic acid continues to be a compound of high interest within pharmaceutical and biomedical research sectors.

Are there any other industrial applications for Shikimic Acid?

Shikimic acid finds utility beyond the pharmaceutical industry in several other sectors, most notably in agriculture and food additives. In agriculture, shikimic acid and its derivatives are explored for their potential as bioherbicides and growth regulators. Their role in plant metabolic pathways can be exploited to develop eco-friendly herbicides that target specific weeds without affecting the surrounding crops. This application aligns with the increasing global emphasis on sustainable farming practices and reducing the environmental impact of chemical herbicides.

In the realm of food additives, shikimic acid is utilized as an antioxidant and preservative. Its ability to scavenge free radicals makes it an attractive ingredient for extending the shelf life of food products and maintaining their nutritional quality. Additionally, due to its presence in many edible plants and fruits, shikimic acid is considered safe for consumption, further promoting its use in the food industry.

Cosmetics and personal care products also benefit from the properties of shikimic acid. Its antioxidant and anti-inflammatory characteristics are advantageous for skincare formulations aimed at combating aging and soothing irritated skin. By protecting the skin from oxidative damage and reducing inflammation, shikimic acid can improve the overall health and appearance of the skin, making it a sought-after ingredient in premium cosmetic lines.

Moreover, shikimic acid’s role in chemical synthesis extends to the production of flavors and fragrances. Aromatic compounds derived from the shikimate pathway can be further synthesized into a variety of flavoring agents and aromatic compounds used in perfumes, enhancing the sensory appeal of consumer products.

In industrial biotechnology, the versatility of shikimic acid paves the way for developing novel bioproducts. Research continues into engineered microorganisms capable of producing shikimic acid and its derivatives more efficiently, which could revolutionize the production processes for many industrial applications.

What are the benefits of using Shikimic Acid in skincare products?

Shikimic acid is gaining recognition in the skincare industry due to its multifaceted benefits. One of its primary advantages is its potent antioxidant property, which helps in combating oxidative stress caused by free radicals. Free radicals are unstable molecules that can cause damage to skin cells, leading to premature aging, fine lines, wrinkles, and loss of skin elasticity. By neutralizing these free radicals, shikimic acid can help in maintaining youthful and healthy skin.

Anti-inflammatory properties of shikimic acid make it an excellent ingredient for soothing irritated or inflamed skin. Inflammation can be a result of various factors including environmental pollutants, UV exposure, and underlying skin conditions like acne or eczema. Shikimic acid helps in mitigating inflammation by reducing the production of inflammatory mediators within the skin cells. This action can lead to reduced redness, swelling, and discomfort, promoting a calmer and more balanced skin appearance.

Additionally, shikimic acid exhibits mild exfoliating properties. It can gently remove dead skin cells from the surface, promoting cell turnover and revealing fresher, more radiant skin underneath. This exfoliation process also aids in unclogging pores, which can prevent acne formation and improve overall skin texture. Unlike some harsher chemical exfoliants, shikimic acid is generally well-tolerated, making it suitable for sensitive skin types.

In the context of hyperpigmentation, shikimic acid can help in evening out skin tone by inhibiting melanin production, the pigment responsible for dark spots and uneven skin tone. Consistent use of skincare products containing shikimic acid can lead to a more uniform complexion, diminishing the appearance of dark spots and pigmentation issues.

Moisturization is another key benefit. Shikimic acid can enhance the skin's natural barrier function, helping to retain moisture and prevent transepidermal water loss. This effect is particularly beneficial for individuals with dry or dehydrated skin, as it aids in keeping the skin hydrated and supple.

With its broad range of skin benefits - from antioxidation and anti-inflammation to exfoliation and moisturization - shikimic acid is proving to be a valuable addition to modern skincare formulations. Its natural origin and compatibility with various skin types further bolster its appeal in the cosmetic industry.

Can Shikimic Acid be synthesized in a lab, and what are the advantages of this?

Yes, shikimic acid can be synthesized in a laboratory setting, and this method offers several significant advantages. Laboratory synthesis of shikimic acid typically involves complex chemical processes that can include the use of fermentation technology with genetically engineered microorganisms, or multi-step organic synthesis starting from simple precursor molecules.

One of the primary advantages of synthesizing shikimic acid in the lab is the ability to produce it on a large scale with greater consistency and purity compared to natural extraction methods. Natural sources of shikimic acid, such as the star anise plant, can vary in shikimic acid content due to factors like growing conditions and plant health. Laboratory synthesis bypasses these variables, providing a more reliable and controlled production process.

Another advantage is sustainability. By shifting production from plant extraction to lab synthesis, there's a considerable reduction in the ecological footprint. Traditional extraction from plants can lead to overharvesting and depletion of natural resources, as well as significant waste generation. In contrast, lab synthesis, especially through microbial fermentation, can be more eco-friendly and sustainable, utilizing renewable resources and generating fewer by-products.

Lab synthesis also allows for the potential of enhancing the yield through genetic engineering and optimization of bacterial or yeast strains used in fermentation. Advances in biotechnology have made it possible to engineer microorganisms that are highly efficient in converting substrates to shikimic acid, thus increasing the overall production yield and cost-effectiveness of the process.

Moreover, synthetically produced shikimic acid can be specifically tailored to meet the stringent purity requirements needed for pharmaceutical applications. Impurities inherent in plant-derived shikimic acid can complicate the purification process, adding to the cost and complexity of production. Synthesis in a controlled lab environment reduces the risk of contamination and allows for the production of highly pure shikimic acid suitable for use in critical medical applications, such as antiviral drug production.

The production scalability afforded by lab synthesis ensures that the supply can meet global demand, especially in times of increased need, such as during influenza outbreaks requiring mass production of antiviral medications like Oseltamivir. This controlled and scalable production method mitigates the risk of supply shortages and price volatility associated with natural sources.

Therefore, synthesizing shikimic acid in a laboratory not only provides a high-purity and consistent product but also aligns with sustainable practices and efficient production methodologies, making it a superior alternative to traditional extraction methods.

What safety considerations should be taken into account when working with Shikimic Acid?

When working with shikimic acid, it is important to follow comprehensive safety protocols to ensure safe handling and usage. Although shikimic acid is an organic compound and generally considered safe, working in an industrial or laboratory setting necessitates certain precautions to prevent any potential hazards.

First and foremost, personal protective equipment (PPE) should be worn at all times. This includes gloves, lab coats, and eye protection such as safety goggles. Shikimic acid in its powdered form can be an irritant upon direct contact with skin or eyes; therefore, minimizing exposure is paramount. In cases where shikimic acid is being manipulated as a fine powder, masks or respirators should also be used to avoid inhalation.

Proper storage is another key consideration. Shikimic acid should be stored in a cool, dry, and well-ventilated area, away from direct sunlight and moisture, as these conditions can affect the stability and quality of the compound. Containers used for storage should be clearly labeled and tightly sealed to prevent contamination and accidental exposure.

Ventilation in the workspace is crucial. Working in a well-ventilated area or using fume hoods can prevent the accumulation of any airborne particles and reduce the risk of inhalation exposure. This is particularly important during processes involving heating or volatilization of the compound.

When it comes to disposal, it is essential to follow local regulations and guidelines for disposing of chemical substances. Shikimic acid waste should not be poured down the drain or discarded with regular trash. Instead, it should be collected in designated chemical waste containers and handled by waste management professionals who can dispose of it appropriately.

Additionally, anyone handling shikimic acid should be trained in basic first aid and emergency procedures. In case of accidental skin contact, the area should be washed thoroughly with soap and water. If the compound gets into the eyes, they should be flushed with plenty of water for at least 15 minutes, and medical attention should be sought. Inhalation incidents require moving to a well-ventilated area and seeking medical advice if symptoms persist.

Monitoring and maintaining up-to-date safety data sheets (SDS) for shikimic acid is also a vital part of ensuring a safe working environment. These documents provide detailed information about the properties of the compound, potential hazards, and specific handling instructions. Regular safety audits and training sessions can help keep all personnel informed and prepared.

By adhering to these safety considerations, the risks associated with handling shikimic acid can be effectively managed, ensuring a safe and controlled working environment.
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