API Shikimic acid

Shikimic acid More Info

General Information

Shikimic acid is a naturally occurring cyclic hydroxy acid with the CAS number 138-59-0. Its systematic chemical name is 3R,4S,5R-trihydroxy-1-cyclohexene-1-carboxylic acid. The molecular formula is C₇H₁₀O₅ with a molecular weight of 174.2 g/mol. It appears as a white crystalline powder with purity levels ranging from ≥95% to ≥98%. The compound is also known by several alternative names including (-)-Shikimic Acid, L-Shikimic Acid, NSC 59257, and Shikimate.

The primary natural source of shikimic acid is Chinese star anise (Illicium verum) fruits. For storage, the product should be kept at -20°C in sealed, light-protected conditions, with a stability period of up to 4 years.

Product Description

Shikimic acid serves as a crucial intermediate in the biosynthesis of aromatic amino acids and other aromatic compounds in plants and microorganisms. First isolated from Japanese star anise, this compound contains three chiral carbons in its molecular structure, making it valuable as a synthetic raw material for various bioactive substances. It is recognized as a multifunctional active ingredient with diverse pharmacological and industrial applications.

Key Properties and Benefits

Pharmaceutical Properties

Shikimic acid exhibits antiviral properties with anti-inflammatory and bactericidal effects. It has anti-thrombotic capabilities that help prevent blood clot formation. The compound demonstrates anti-inflammatory activity that reduces inflammation in various tissues and possesses antioxidant properties that protect cells from oxidative damage.

Cosmetic Properties

In cosmetics, shikimic acid provides multiple skin benefits. It reduces melanin production and brightens skin tone through the inhibition of tyrosinase activity. The ingredient offers anti-acne benefits by inhibiting bacteria that cause skin inflammation. It provides gentle natural exfoliation that removes dead skin cells. Additional benefits include anti-dandruff action effective against scalp issues, and deodorant properties that inhibit lipase enzyme activity to reduce unpleasant body odor. The compound also promotes collagen and elastin synthesis, contributing to anti-aging effects.

Industrial Properties

Beyond pharmaceutical and cosmetic applications, shikimic acid serves as an essential precursor for oseltamivir (Tamiflu) synthesis in the pharmaceutical industry. It functions as a nanoparticle stabilizer in material science applications and acts as a cosmetic preservative that extends the shelf life of food products.

Applications by Industry

Pharmaceutical Industry Applications

In pharmaceuticals, shikimic acid is the primary raw material for Tamiflu (oseltamivir) production, making it critical for antiviral medication manufacturing. The compound has been studied for cerebral protection after ischemia and reperfusion events. It is widely used in biomedical research for cell differentiation studies and drug development programs.

Cosmetic Industry Applications

The cosmetic industry has seen significant adoption of shikimic acid, with over 1,100 cosmetic formulations globally including the ingredient in 2023, up from 890 in 2021. Major skincare brands launched over 65 new products featuring shikimic acid as a key ingredient during the same period. Applications include chemical peels, acne treatments, anti-aging serums, whitening products, and deodorants. Europe and Japan consumed approximately 76% of the cosmetic usage, representing over 130 metric tons.

Food Industry Applications

In the food sector, shikimic acid functions as a natural preservative that inhibits the growth of harmful microorganisms. Its antioxidant properties help prevent fat oxidation and maintain food freshness. The ingredient is also added to functional foods and beverages for immune-regulating functions.

Material Science Applications

Shikimic acid is used for stabilization of metal nanoparticles, with silver nanoparticles ranging from 90-105 nm and gold nanoparticles from 60-80 nm. The compound also facilitates collagen cross-linking for tissue engineering applications.

Physical and Chemical Properties

The solubility profile of shikimic acid shows good dissolution in aqueous and organic solvents. The compound dissolves at approximately 10 mg/mL in water or PBS at pH 7.2, and 2.5 mg/mL in ethanol. For laboratory applications, concentrations up to 25 mg/mL are achievable in DMSO and DMF. However, shikimic acid remains insoluble in chloroform, benzene, and petroleum ether.

Additional physical characteristics include a melting point range of 185°C to 191°C, optical rotation of -180°, and UV-Vis absorption with λmax at 213 nm. The supply form is typically a crystalline solid.

Laboratory Usage Guidelines

Stock Solution Preparation

To prepare stock solutions, dissolve the compound in appropriate organic solvents such as ethanol, DMSO, or DMF. Use inert gas purging to remove impurities before use. Dilute to aqueous buffer or isotonic saline for biological experiments. Stock solutions should not be stored for more than 1 day to avoid solvent residue effects.

Safety Precautions

Contraindications for topical use include pregnancy, lactation, skin infections, sunburn, antibiotic treatment, and dermatological conditions such as psoriasis and eczema. When applying shikimic acid products during daytime hours, SPF protection is recommended.

Market Overview

The shikimic acid market is experiencing significant growth driven by increasing demand for natural and organic cosmetics, rising consumer awareness of skincare benefits, expansion of pharmaceutical applications, and growth in functional food and beverage sectors. New formulations in dermatological products continue to emerge, supporting sustained market expansion.

Conclusion

Shikimic acid stands as a versatile and valuable compound with extensive applications across pharmaceutical, cosmetic, food, and material science industries. Its natural origin, combined with diverse biological activities including antiviral, anti-inflammatory, antioxidant, and skin-brightening properties, makes it an indispensable ingredient for modern formulations. The continued innovation in product development and growing consumer preference for bioactive, naturally-derived ingredients ensure sustained demand for shikimic acid in the coming years.