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Send EmailEucalyptol, Cineol, Cineole, 470-82-6
CAS No: 470-82-6 | EC No: 207-431-5 | Molecular Formula: C₁₀H₁₈O | Molecular Weight: 154.25 g/mol
| Parameter | Value | Description |
|---|---|---|
| Appearance | Colorless to pale yellow liquid | Clear, mobile liquid |
| Odor | Fresh, minty, camphoraceous, spicy | Characteristic eucalyptus scent |
| Taste | Cooling, spicy, slightly bitter | Triggers cold receptors (TRPM8) |
| Melting Point | 2.9°C (37.2°F) | Solidifies near room temperature |
| Boiling Point | 176-177°C (349-351°F) | Moderate volatility |
| Flash Point | 49°C (120°F) (Closed cup) | Flammable liquid |
| Density (20°C) | 0.921-0.927 g/cm³ | Slightly less dense than water |
| Refractive Index (20°C) | 1.456-1.460 | |
| Vapor Pressure (25°C) | ~1.5 mbar | Low volatility |
| Solubility in Water | ~3.5 g/L (slightly soluble) | Forms cloudy mixtures |
| Solubility in Organic Solvents | Miscible with ethanol, oils, ethers, chloroform | Excellent lipophilicity |
| log P (Octanol-Water) | 2.74 | Moderately lipophilic |
| Autoignition Temperature | ~260°C (500°F) |
Eucalyptol is often compared with menthol, camphor, and thymol in pharmaceutical and cosmetic applications.
| Property | Eucalyptol (1,8-Cineole) | Menthol | Camphor | Thymol | Limonene |
|---|---|---|---|---|---|
| Source | Eucalyptus, rosemary, tea tree | Mint oils (peppermint, cornmint) | Camphor tree (Cinnamomum camphora) | Thyme oil (Thymus vulgaris) | Citrus peels |
| Chemical Class | Cyclic ether (terpenoid) | Cyclic monoterpene alcohol | Cyclic ketone | Phenolic monoterpene | Cyclic terpene |
| Primary Effect | Mucolytic, anti-inflammatory | Cooling (TRPM8 agonist), analgesic | Counterirritant, decongestant | Antifungal, antiseptic | Solvent, degreaser |
| Cooling Sensation | Moderate (indirect) | Strong (direct TRPM8) | None (warm/irritant) | Mild | None |
| Boiling Point | 177°C | 216°C | 209°C | 232°C | 176°C |
| Oral LD50 (rat) | ~2,500 mg/kg | ~3,300 mg/kg | ~5,000 mg/kg | ~980 mg/kg (toxic) | ~4,400 mg/kg |
| Skin Irritation | Low (may sensitize) | Low-moderate | High (avoid mucous membranes) | Moderate-high | Low-moderate |
| Solubility in Water | Slightly soluble (3.5 g/L) | Very slightly soluble (1.4 g/L) | Very slightly soluble | Slightly soluble | Insoluble |
| GRAS Status (FDA) | Yes (flavor, <10 ppm) | Yes | Yes (topical only) | Yes (≤0.1%) | Yes |
| Typical Use | Cough syrup, mouthwash, spray | Topical rub, candy, cigarettes | Topical rub, plasticizer | Mouthwash, disinfectant | Degreaser, fragrance |
vs. Menthol: Better mucolytic activity; works deeper in respiratory tract.
vs. Camphor: Lower skin irritation; safe for inhalation.
vs. Thymol: Milder taste; better for oral formulations.
vs. Limonene: Soluble enough for water-based formulations; bioactive.
| Plant Source | Eucalyptol Content (% of essential oil) |
|---|---|
| Eucalyptus globulus (Blue Gum) | 70-90% |
| Eucalyptus polybractea (Blue Mallee) | 85-95% |
| Rosmarinus officinalis (Rosemary CT Cineole) | 40-55% |
| Melaleuca alternifolia (Tea Tree) | 5-15% |
| Laurus nobilis (Bay Laurel) | 30-50% |
| Salvia officinalis (Sage) | 15-30% |
| Cardamomum (Cardamom) | 25-40% |
| Artemisia herba-alba (White Wormwood) | 30-50% |
Note: Pure eucalyptol (≥99%) is typically produced by fractional distillation of Eucalyptus globulus oil, not by synthesis.
Generic formulations. No brand names used. Adjust percentages based on regulatory limits.
| Ingredient | Function | Concentration (% w/v) |
|---|---|---|
| Eucalyptol (≥99%) | Active: mucolytic, anti-inflammatory | 0.5-1.0% |
| Guaifenesin | Expectorant (optional synergy) | 2.0% |
| Ethanol (95%) | Solubilizer | 10.0% |
| Glycerin | Sweetener, viscosity | 20.0% |
| Citric acid | pH adjuster (pH 4.5-5.0) | 0.1% |
| Sodium benzoate | Preservative | 0.1% |
| Purified water | Vehicle | to 100% |
Directions: 5-10 mL every 4-6 hours (adults). Not for children under 6 years without medical advice.
| Ingredient | Function | Concentration (% w/v) |
|---|---|---|
| Eucalyptol | Antiseptic, anti-inflammatory | 0.09% |
| Thymol | Antifungal, antiseptic | 0.06% |
| Menthol | Cooling, mild analgesic | 0.06% |
| Methyl salicylate | Anti-inflammatory (mild) | 0.06% |
| Poloxamer 407 | Solubilizer | 1.0% |
| Glycerin | Humectant, sweetness | 10.0% |
| Sodium saccharin | Sweetener | 0.05% |
| Purified water | Vehicle | to 100% |
Usage: Rinse 20 mL for 30 seconds twice daily. Reduces plaque, gingivitis, and halitosis.
| Ingredient | Function | Concentration (% w/w) |
|---|---|---|
| Eucalyptol | Mucolytic, decongestant | 5.0% |
| Menthol | Cooling, counterirritant | 2.5% |
| Camphor (synthetic) | Mild decongestant | 5.0% |
| Thyme oil (thymol CT) | Antimicrobial | 0.5% |
| Nutmeg oil | Warming sensation | 0.5% |
| Petrolatum (white soft paraffin) | Base | to 100% |
Usage: Apply thin layer to chest and throat (not on face). For adults and children ≥2 years.
| Ingredient | Function | Concentration (% volume) |
|---|---|---|
| Eucalyptol (pure) | Mucolytic, bronchodilator | 50% |
| Peppermint oil (high menthol) | Cooling, enhances penetration | 30% |
| Lemon oil (limonene) | Mood uplifting, mild antiseptic | 20% |
Usage: Add 3-5 drops to diffuser or bowl of hot water for steam inhalation. Do not apply undiluted to skin.
| Ingredient | Function | Concentration (% v/v) |
|---|---|---|
| Eucalyptol | Antimicrobial | 2.0% |
| Ethanol (70%) | Solvent, primary disinfectant | 60.0% |
| Distilled water | Diluent | 38.0% |
| Lemon essential oil | Fragrance, degreasing | optional (0.5%) |
Efficacy: Effective against S. aureus, E. coli, Candida albicans (contact time ≥5 minutes).
| Effect | Mechanism |
|---|---|
| Mucolytic | Increases ciliary beat frequency (CBF) by activating TRPA1 channels; stimulates airway hydration via CFTR chloride channels. |
| Anti-inflammatory | Inhibits NF-κB pathway; reduces COX-2 expression and prostaglandin E2 (PGE2); decreases TNF-α and IL-1β. |
| Antimicrobial | Disrupts bacterial cell membranes (Gram-positive > Gram-negative); inhibits biofilm formation; synergistic with antibiotics. |
| Bronchodilator | Relaxes smooth muscle via calcium channel blockade (mild, less than beta-agonists). |
| Antioxidant | Scavenges reactive oxygen species (ROS); upregulates glutathione. |
| Cooling sensation | Activates TRPM8 receptors (weak, indirect via menthol-like structure). |
| Region | Status |
|---|---|
| FDA (USA) | GRAS (Generally Recognized as Safe) for flavoring at ≤10 ppm in food. Over-the-counter (OTC) monograph for cough/cold (CFR 341). |
| EFSA (EU) | Permitted as food flavoring (FL No: 03.001). Maximum levels vary by food category. |
| WHO | Listed in essential medicines list (as part of eucalyptus oil, not pure). |
| REACH (EU) | Registered; no SVHC (Substance of Very High Concern) classification. |
| Cosmetic Regulation (EU) | Permitted; restricted in Japan (max 0.3% in rinse-off products). |
| Parameter | Value |
|---|---|
| Oral LD50 (rat) | 2,480 mg/kg (moderately toxic in high doses) |
| Dermal LD50 (rabbit) | >5,000 mg/kg (low toxicity) |
| Inhalation LC50 (rat, 4h) | 14 mg/L (mildly toxic) |
| Skin irritation (rabbit) | Mild (non-irritant at ≤20%) |
| Eye irritation (rabbit) | Moderate (rinse immediately) |
| Skin sensitization | Low; rare cases in sensitive individuals |
| Genotoxicity | Negative (Ames test, micronucleus) |
| Reproductive toxicity | No evidence at low doses; avoid high doses during pregnancy |
| Hazard Class | Statement |
|---|---|
| Acute toxicity (oral) | Category 4 (H302: Harmful if swallowed) |
| Skin irritation | Category 3 (H316: Mild skin irritation) |
| Eye irritation | Category 2A (H319: Causes serious eye irritation) |
| Flammable liquid | Category 3 (H226: Flammable liquid and vapor) |
| Exposure | Action |
|---|---|
| Inhalation | Remove to fresh air. If breathing difficulty, give oxygen. |
| Skin contact | Wash with soap and water for 15 minutes. |
| Eye contact | Rinse with water for 15 minutes; seek medical attention if persistent irritation. |
| Ingestion | Do NOT induce vomiting. Rinse mouth. Give activated charcoal if >10 mL ingested (medical supervision). |
A: No. Eucalyptus oil contains 70-90% eucalyptol plus other terpenes (limonene, α-pinene, globalol, aromadendrene). Pure eucalyptol (≥99%) is a standardized, colorless compound. Eucalyptus oil has a broader, more complex aroma and different safety profile (higher skin irritation due to other terpenes).
A: Yes, in small regulated amounts (typically 0.5-1.5 mg per dose). The FDA allows eucalyptol in OTC cough/cold products. However, swallowing large amounts (>1 g pure eucalyptol or >10 mL eucalyptus oil) can cause nausea, vomiting, dizziness, respiratory depression, seizures, and even death. Never ingest undiluted eucalyptol.
A: In small amounts (cough drops, diluted inhalation), it is generally considered safe. However, high doses or topical application of concentrated eucalyptol should be avoided during pregnancy due to lack of safety data. Always consult a physician before using during pregnancy or lactation.
A: Some in vitro studies show eucalyptol inhibits SARS-CoV-2 replication and reduces inflammatory cytokines. However, there is no clinical evidence that eucalyptol treats or prevents COVID-19. It may help relieve symptoms (cough, congestion) but does not cure the viral infection.
A: Not directly.
Menthol: Strong cooling sensation (direct TRPM8 agonist), used for topical analgesia.
Eucalyptol: Weak cooling, better mucolytic/anti-inflammatory activity.
They are often used synergistically (e.g., 5 parts eucalyptol : 1 part menthol for respiratory products).
A:
Inhalation (steam): Diluted (2-3 drops in 1L hot water) for children ≥6 years.
Oral (cough drops): Only for children ≥6 years (choking hazard and dose concerns).
Topical chest rub: For children ≥2 years (avoid face and mucous membranes).
NEVER give pure eucalyptol or eucalyptus oil orally to infants or young children (risk of laryngospasm, CNS depression).
A: Yes, eucalyptol is FDA GRAS as a flavoring agent in very low concentrations (typically <10 ppm in baked goods, candy, beverages, ice cream). It provides a cooling, spicy, minty note. However, it is not approved as a direct food additive in high amounts (no nutritional function).
A: UN 1993 (Flammable liquid, n.o.s.) or UN 1169 (Extracts, aromatic, liquid). Packing group: III (lowest hazard among flammable liquids). Proper shipping name: "Flammable liquid, n.o.s. (1,8-cineole)."
A:
Store in tightly sealed, dark glass or HDPE containers (avoid oxygen and light).
Keep in a cool, well-ventilated area away from ignition sources (flash point 49°C).
Avoid contact with strong oxidizers (peroxides, nitric acid).
Shelf life: 24 months (if stored properly; test for peroxide formation after 12 months).
A:
Compatible: Glass, stainless steel (SS304/316), HDPE, PTFE (Teflon), Viton.
Incompatible: Natural rubber, neoprene, EPDM, PVC (softens/swells), low-density polyethylene (LDPE - permeation).
A:
CYP450 interactions: Eucalyptol inhibits CYP2B6 and CYP3A4 (mild). May increase levels of drugs metabolized by these enzymes (e.g., midazolam, ketamine, certain antivirals).
Synergy: Enhances penetration of topical drugs (e.g., lidocaine, antifungals) through skin/mucosa.
Always consult a physician if taking prescription medications.
A: Yes, but with extreme caution. Cats and dogs are more sensitive than humans (lack of glucuronidation enzymes).
Safe for horses/cattle: Low doses for respiratory conditions.
TOXIC to cats: Even small amounts (eucalyptus oil) can cause drooling, tremors, liver failure.
Moderate toxicity to dogs: Diluted use only; avoid ingestion.
Always consult a veterinarian before using on pets.
| Pros | Cons |
|---|---|
| Natural origin (renewable) | Toxic in high oral doses (>2 g) |
| Effective mucolytic and anti-inflammatory | Slightly soluble in water (requires solubilizer) |
| Pleasant, fresh odor | Moderate flammability (flash point 49°C) |
| Low skin irritation (compared to camphor) | May cause eye irritation |
| GRAS status for flavor (FDA/EFSA) | Incompatible with many plastics |
| Synergistic with menthol and thymol | Not suitable for children under 6 years |
| Antimicrobial (plaque, gingivitis) | Not vegan-certified (if animal testing involved) |