Overview
(-)-Fenchone Standard is the levorotatory enantiomer of the bicyclic monoterpene ketone fenchone, primarily isolated from fennel (Foeniculum vulgare) and other aromatic plants. As a certified reference material, it meets pharmacopeial standards (USP/EP) for use in quantitative analysis. The compound's rigid bicyclic structure and chiral center make it valuable for studying stereochemical effects in organic chemistry. In industrial contexts, manufacturers typically supply it in amber glass vials with ≥98% chemical and enantiomeric purity, accompanied by comprehensive analytical documentation.
Physical and Chemical Properties
(-)-Fenchone exhibits characteristic physical properties of terpenoid ketones, including a relatively low melting point and moderate volatility. Its density of 0.948 g/cm³ makes it lighter than water, while the boiling point of 193-195°C allows for easy purification via distillation. Chemically, the compound demonstrates typical ketone reactivity but is stabilized by its bridged ring system. The (-)-enantiomer shows specific optical rotation of approximately -66° (neat), serving as a key identifier. Its solubility profile favors organic solvents, with limited water solubility of about 0.1 g/L at room temperature.
Main Applications
In analytical laboratories, (-)-Fenchone Standard serves as a crucial calibration standard for gas chromatography (GC) and high-performance liquid chromatography (HPLC) methods, particularly in essential oil authentication. Its distinctive retention indices help identify adulteration in botanical extracts. The fragrance industry utilizes this enantiomer for its fresh, camphoraceous notes in premium perfumes and aromatherapy products. Pharmaceutical researchers investigate its potential as a chiral building block and for reported biological activities, including antimicrobial and anti-inflammatory effects.
Safety and Storage
As a flammable liquid with mild irritant properties, (-)-Fenchone requires careful handling per GHS guidelines. Safety Data Sheets (SDS) recommend using nitrile gloves, safety goggles, and fume hoods during manipulation to prevent contact with skin/eyes or inhalation of vapors. Proper storage involves refrigeration (2-8°C) in tightly sealed amber glass containers under inert gas when possible. Under these conditions, the standard typically maintains stability for 24-36 months. Degradation signs include discoloration or changes in optical rotation values.
B2B Procurement Guide
When sourcing (-)-Fenchone Standard, B2B buyers should prioritize suppliers who provide: 1) Batch-specific certificates of analysis documenting enantiomeric excess (ee), 2) Validated stability data, and 3) Traceability to reference materials from recognized institutions like NIST. Technical specifications should confirm compliance with relevant industry standards (e.g., ISO 17034 for reference materials). Procurement contracts often include clauses for analytical method support and replacement guarantees in case of qualification test failures. Bulk orders (100g+) may attract 15-30% price discounts but require verification of appropriate storage capacity.
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