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.