Product Details
Shikimic acid is a white crystalline compound with high water solubility (180 g/L at 20°C). Its name originates from shikimi grass (Illicium anisatum), a Japanese plant from which it was first isolated. This compound functions as a crucial metabolic intermediate in plants and microorganisms.
Traditionally, the primary source of shikimic acid has been the dried ripe fruits of Illicium species, particularly Japanese star anise. Recent studies have investigated alternative extraction methods, including isolation from the fruits of sweetgum trees (Liquidambar formosana) and pine needles.
As a white crystalline cyclohexene carboxylic acid, shikimic acid possesses three chiral centers (3R,4S,5R configuration) and serves as the biochemical precursor to aromatic amino acids (phenylalanine, tyrosine, tryptophan) in the shikimate pathway.
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 |
