Shikimic acid is a white crystalline substance with high water solubility. It derives its name from shikimi grass (Illicium anisatum), a Japanese plant from which it was initially obtained. This compound serves as a key metabolic intermediate in both plants and microorganisms.
Traditionally, the primary source of shikimic acid has been the dried ripe fruits of Illicium species, particularly Japanese star anise (Illicium anisatum). However, recent studies have explored alternative extraction methods, including isolating shikimic acid from the fruits of sweetgum trees (Liquidambar formosana) and pine needles.
A white crystalline cyclohexene carboxylic acid with high water solubility (180 g/L at 20°C), named after Japanese shikimi grass (Illicium anisatum). This key metabolic intermediate features three chiral centers (3R,4S,5R configuration) and serves as the biochemical precursor to aromatic amino acids (phenylalanine, tyrosine, tryptophan) in the shikimate pathway.
| 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)
| 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 |
