Product Overview
Shikimic Acid (CAS#138-59-0) is a naturally occurring white crystalline cyclohexene carboxylic acid with excellent water solubility. It was originally isolated from Japanese star anise (Illicium anisatum), from which its name was derived.
As an important metabolic intermediate found in plants and microorganisms, Shikimic Acid plays a central role in the shikimate pathway, serving as a precursor for aromatic amino acids such as phenylalanine, tyrosine, and tryptophan. The molecule contains three chiral centers with a specific 3R,4S,5R configuration, making it highly valuable in stereoselective chemical synthesis.
With its unique biological activity, high solubility, and broad application potential, Shikimic Acid is widely utilized in pharmaceutical research, biotechnology, chemical synthesis, and specialty ingredient development. It is also being explored for applications in areas such as cosmetics, functional materials, and sustainable bioprocessing.
Key Properties & Specifications
| Parameter | Value |
| Molecular Weight | 174.15 g/mol |
| Melting Point | 185-187°C (decomp.) |
| Specific Rotation | [α]₂₀ᴰ = -171° (c=1, H₂O) |
| pKa Values | pKa₁=4.04, pKa₂=5.85 |
| Log P (octanol-water) | -1.38 |
| UV Absorption | λ<sub>max</sub> = 214 nm |
| Thermal Stability | Degrades >200°C |
Production Methods & Sources
1. Traditional Plant Extraction
| Source | Shikimic Acid Yield | Extraction Process |
| Japanese Star Anise (Illicium anisatum) | 3-5% dry weight | - Acid hydrolysis (H₂SO₄) - Ion-exchange purification |
| Chinese Star Anise (I. verum) | 5-8% dry weight | - Ethanol reflux - Crystallization (pH 3.5) |
| Sweetgum (Liquidambar spp.) | 1.2-2.1% dry weight | - Alkaline hydrolysis - Activated carbon filtration |
| Pine Needles (Pinus spp.) | 0.3-0.8% dry weight | - Supercritical CO₂ extraction - HPLC isolation |
2. Fermentation (Dominant Industrial Method)
Engineered E. coli: Yields >70 g/L (glucose feedstock)
Strain: E. coli K12/ΔaroL/ΔaroK
Fermentation: 37°C, pH 7.0, 60 hrs
3. Chemical Synthesis
Asymmetric Route: Diels-Alder of furan with acrylic acid (enantiomeric excess >98%)
Cost: $2,500/kg (vs. $400/kg for fermentation)
Industrial Applications
1. Pharmaceutical Synthesis
Oseltamivir Phosphate (Tamiflu®):
Key intermediate: 70% of global SA demand
Reaction:
Shikimate→10 stepsOseltamivirShikimate10stepsOseltamivir
Antivirals: Zanamivir (Relenza®), Peramivir
Antibiotics: Chloramphenicol, Mycobacterium inhibitors
2. Biotechnology
Shikimate Pathway Engineering: CRISPR-modified crops (drought-resistant maize)
Biocatalysis: Chiral synthon for unnatural amino acids
3. Food & Agriculture
Plant Elicitor: Enhances phenolic compound production in grapes (wine quality)
Preservative: Inhibits E. coli O157:H7 (MIC = 12.5 mg/mL)
4. Cosmetics
Skin Brightener: Tyrosinase inhibitor (0.5-2% in serums)
Anti-Inflammatory: Reduces TNF-α in keratinocytes
Technical Grades & Specifications
| Grade | Purity | Key Impurities | Applications |
| Pharma Grade | >99.5% | Aromatic AA <0.1% | Antiviral synthesis |
| Food Grade | >98.0% | Heavy metals <10 ppm | Functional ingredients |
| Research Grade | >99.9% | Endotoxin <0.01 EU/mg | Enzyme kinetics studies |
| Industrial | >95.0% | Water <0.5% | Agrochemical synthesis |
Packaging Options
| Format | Capacity | Material |
| Glass Vials | 1-100 g | Amber glass + PTFE seal |
| HDPE Bottles | 0.5-5 kg | Nitrogen headspace |
| Fiber Drums | 25 kg | Double PE liner |
| Custom Bulk | >100 kg | Vacuum-sealed bags |
