Supply High Purity Nootkatone CAS 4674-50-4

I. Overview

1. Chemical Properties and Sources
   • Chemical Structure: Nootkatone is a sesquiterpene ketone with the molecular formula C₁₅H₂₂O (molecular weight: 218.33; CAS No.: 4674-50-4). It occurs as a colorless to pale yellow oily liquid, with pure crystals appearing white. It exhibits a sharp, fruity aroma reminiscent of grapefruit, complemented by cedar-like undertones and a slight bitterness.
   • Solubility: Insoluble in water but soluble in organic solvents such as ethanol and oils. Key physicochemical properties: relative density 0.96 g/cm³, melting point 35–39°C, boiling point 190°C/0.13 KPa. Sensitive to heat and humidity.
   • Natural Sources: Found in essential oils of grapefruit peel, Alaskan yellow cedar (Chamaecyparis nootkatensis), bergamot, lemon, and other plants.
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2. Biosynthesis and Preparation
   • Bioconversion: Efficiently synthesized from (+)-valencene (a precursor) via microbial transformation using organisms like Chlorella vulgaris, Mucor spp., or Botryosphaeria dothidea. For example, C. vulgaris converts valencene into nootkatone with 89% GC-MS peak area and 63% isolated yield over 18 days.
   • Chemical Synthesis: Traditional methods involve toxic heavy metals, prompting a shift toward green synthesis (e.g., enzymatic fermentation) for cost-effective, eco-friendly production.

II. Applications

1. Flavor and Fragrance Industry
   • Food Flavorings: Used to formulate grapefruit, orange, tropical fruit, and other edible fragrances, imparting a characteristic grapefruit note with sweet citrus-peel and woody nuances. Recommended dosage: ≤10 mg/kg in final food products.
   • Tobacco Additives: Enhances cigarette aroma, mellows smoke flavor, and reduces irritation.
   • Cosmetic Fragrances: Incorporated into perfumes, skincare products, etc., for a refreshing, long-lasting citrus scent.
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2. Insect Repellents and Pesticides
   • High-Efficacy Repellency: Demonstrates potent repellent and insecticidal activity against deer ticks, lone star ticks, mosquitoes, bed bugs, head lice, and other pests. EPA-approved as a spray-based repellent, providing hours of mosquito protection with low human toxicity.
   • Eco-Friendly Profile: A volatile essential oil with minimal environmental persistence, ensuring safety for non-target organisms and serving as an ideal biopesticide.
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3. Pharmaceutical Applications
   • Antiplatelet Activity: Inhibits platelet aggregation induced by collagen, thrombin, and arachidonic acid (AA), suggesting potential for preventing platelet-related cardiovascular diseases.
   • Antitumor Potential: Suppresses proliferation of human nasopharyngeal carcinoma cell lines (HNE1, HNE2, HONE1, CNE1), indicating promise for antineoplastic drug development.
   • Additional Pharmacology: Exhibits anti-allergic, anti-inflammatory, and antiproliferative effects, with potential therapeutic applications in diverse conditions.
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4. Agricultural and Household Uses
   • Crop Protection: Enables the development of natural botanical pesticides to replace synthetic chemicals, reducing environmental pollution.
   • Household Products: Added to cleansers, soaps, and detergents for natural fragrance and insect-repellent properties.