Product Description
Shikimic acid is a water-soluble white crystalline cyclohexene carboxylic acid, boasting a high aqueous solubility of 180 g/L at 20°C. It takes its nomenclature from Illicium anisatum, a traditional Japanese shikimi plant that acted as its original extraction source.
Possessing a stable chiral molecular structure with 3R,4S,5R stereoscopic configurations, it functions as a vital biological metabolic intermediate. It dominates the shikimate biosynthetic pathway, acting as a core precursor for synthesizing essential aromatic amino acids including phenylalanine, tyrosine and tryptophan in plants and microbes.
Natural shikimic acid is conventionally extracted from dried star anise fruits. With technological advancement, diversified raw material sources such as sweetgum fruits and pine needles have been developed, enabling more flexible and sustainable raw material acquisition for industrial production.
Product Parameters
| 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)
Application Scenarios
Pharmaceutical Manufacturing
Shikimic acid serves as a critical chiral precursor for high-end antiviral and antibacterial pharmaceuticals. It is the dominant raw material for synthesizing Oseltamivir phosphate (Tamiflu), satisfying the majority of global market demand. It also supports the production of other mainstream antivirals including Zanamivir and Peramivir, as well as specialized antibiotics and Mycobacterium inhibitors for clinical treatment.
Biotechnology & Synthetic Biology
Leveraging its unique chiral structure, it acts as a premium chiral building block for biocatalytic synthesis of unnatural amino acids. Through shikimate pathway modification, it enables genetic optimization of stress-resistant crops such as drought-tolerant maize, empowering modern agricultural biotech breeding.
Food & Agricultural Industry
It functions as an efficient natural food preservative, effectively inhibiting harmful pathogens like E. coli O157:H7 with clear minimum inhibitory concentration performance. In viticulture, it acts as a plant elicitor to boost phenolic metabolite accumulation in grapes, significantly improving wine flavor and quality.
Cosmetic Personal Care
Widely applied in skincare formulations at 0.5–2% dosage, it inhibits tyrosinase activity to brighten skin tone. It also delivers potent anti-inflammatory effects by reducing TNF-α expression in keratinocytes, soothing skin irritation and enhancing skin stability.
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 Option
| 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 |
