EUCALYPTOL – OKALİPTOL

CAS Number: 470-82-6
EC Number (EINECS): 207-431-5
Molecular Formula: C₁₀H₁₈O
Molecular Weight: 154.25 g/mol
Chemical Class: Cyclic ether (terpenoid)

SECTION 1: CHEMICAL IDENTITY AND DEFINITION

Parameter	Information
Chemical Name (IUPAC)	1,3,3-Trimethyl-2-oxabicyclo[2.2.2]octane
Other Names	Eucalyptol, 1,8-Cineole, Cineol, 1,8-Epoxy-p-menthane, Cajuputol
Chemical Formula	C₁₀H₁₈O
Molecular Weight	154.25 g/mol
CAS Number	470-82-6
EC Number (EINECS)	207-431-5
Chemical Class	Cyclic ether (terpenoid)
Appearance	Colorless to pale yellow, clear liquid
Odor	Fresh, minty, camphoraceous, spicy
Taste	Cooling, spicy, slightly bitter
Physical State (20°C)	Liquid
Source	Eucalyptus, rosemary, tea tree, bay leaf
E Number	Not assigned

SECTION 2: PHYSICAL PROPERTIES

Property	Value
Appearance	Colorless to pale yellow, clear liquid
Odor	Fresh, minty, camphoraceous, spicy
Taste	Cooling, spicy, slightly bitter
Molecular Weight	154.25 g/mol
Melting Point	2.9 °C
Boiling Point	176 – 177 °C
Flash Point	49 °C (closed cup)
Density (20°C)	0.921 – 0.927 g/cm³
Refractive Index (nD²⁰)	1.456 – 1.460
Vapor Pressure (25°C)	~1.5 mbar
Solubility in Water	Slightly soluble (~3.5 g/L)
Solubility in Ethanol	Miscible
Solubility in Oils	Miscible
Solubility in Organic Solvents	Miscible (ether, chloroform)
Log P (octanol/water)	2.74
Autoignition Temperature	~260 °C

SECTION 3: CHEMICAL PROPERTIES

Property	Information
Chemical Formula	C₁₀H₁₈O
Molecular Weight	154.25 g/mol
Chemical Class	Cyclic ether (terpenoid)
Functional Groups	Ether (-O-)
Structure	Bicyclic monoterpenoid ether
SMILES	CC1(C)C2CCC1(C)OC2
InChI Key	WEEGYLXZBRQIMU-UHFFFAOYSA-N
Stability	Stable under normal storage conditions
Oxidation	Slowly oxidizes in air
Incompatible Materials	Strong oxidizing agents, strong acids, strong bases

Chemical Structure:

     CH₃
      |
    O-CH
   /     \
  C       C
 / \     / \
CH₃ C---C   C
    |       |
    CH₃     CH₂
      \   /
       C-C
         |
         CH₃

1,8-Cineole / Eucalyptol

SECTION 4: NATURAL SOURCES

Source	Eucalyptol Content (%)
Eucalyptus globulus (Blue Gum)	70-90%
Eucalyptus polybractea (Blue Mallee)	85-95%
Rosmarinus officinalis (Rosemary - Cineole Chemotype)	40-55%
Melaleuca alternifolia (Tea Tree)	5-15%
Laurus nobilis (Bay Leaf)	30-50%
Salvia officinalis (Sage)	15-30%
Elettaria cardamomum (Cardamom)	25-40%
Artemisia herba-alba (White Wormwood)	30-50%

SECTION 5: PHARMACOLOGICAL MECHANISM

Effect	Mechanism
Mucolytic	Activates TRPA1 channels; increases ciliary beat frequency (CBF); stimulates airway hydration via CFTR chloride channels
Anti-inflammatory	Inhibits NF-κB pathway; reduces COX-2 expression and prostaglandin E2 (PGE2); lowers TNF-α and IL-1β
Antimicrobial	Disrupts bacterial cell membranes (Gram-positive > Gram-negative); inhibits biofilm formation; synergistic with antibiotics
Bronchodilator	Smooth muscle relaxation (via calcium channel blockade; weaker than beta-agonists)
Antioxidant	Scavenges reactive oxygen species (ROS); upregulates glutathione
Cooling Sensation	Activates TRPM8 receptors (weak; indirect via menthol-like structure)

SECTION 6: COMPARISON WITH ALTERNATIVE COMPOUNDS

Property	Eucalyptol	Menthol	Camphor	Thymol
Chemical Class	Cyclic ether	Cyclic alcohol	Cyclic ketone	Phenolic monoterpene
Primary Effect	Mucolytic, anti-inflammatory	Cooling, analgesic	Irritant, decongestant	Antifungal, antiseptic
Cooling Sensation	Moderate	Strong	None	Mild
Boiling Point	177°C	216°C	209°C	232°C
Oral LD50 (Rat)	~2,500 mg/kg	~3,300 mg/kg	~5,000 mg/kg	~980 mg/kg
Skin Irritation	Low	Low-Medium	High	Medium-High
GRAS Status	Yes	Yes	Yes	Yes

SECTION 7: APPLICATION AREAS

7.1. Pharmaceutical Applications

Application	Function
Cough Syrups	Mucolytic, anti-inflammatory, expectorant
Throat Lozenges	Soothing, antimicrobial
Chest Rubs	Decongestant, bronchodilator
Inhalation Solutions	Respiratory support
Mouthwashes	Antiseptic, anti-inflammatory
Topical Analgesics	Anti-inflammatory

7.2. Food Industry

Application	Function
Flavoring Agent	Cooling, minty, spicy note (GRAS, <10 ppm)
Beverages	Fresh, cooling flavor
Confectionery	Mint flavor enhancement
Baked Goods	Flavor component

7.3. Cosmetic and Personal Care

Application	Function
Toothpastes	Antimicrobial, breath freshening
Mouthwashes	Antimicrobial, anti-plaque
Skin Care	Anti-inflammatory, antimicrobial
Fragrances	Fresh, minty note

7.4. Household Products

Application	Function
Disinfectants	Antimicrobial, deodorizing
Air Fresheners	Fresh, clean scent
Cleaning Products	Natural antimicrobial

SECTION 8: FORMULATION EXAMPLES

8.1. Expectorant Cough Syrup (Adult Dose)

Component	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	Carrier	q.s. to 100

8.2. Antimicrobial Mouthwash (Alcohol-Free)

Component	Function	Concentration (% w/v)
Eucalyptol	Antiseptic, anti-inflammatory	0.09
Thymol	Antifungal, antiseptic	0.06
Menthol	Cooling, mild analgesic	0.06
Methyl Salicylate	Mild anti-inflammatory	0.06
Poloxamer 407	Solubilizer	1.0
Glycerin	Humectant	10.0
Sodium Saccharin	Sweetener	0.05
Purified Water	Carrier	q.s. to 100

SECTION 9: REGULATORY STATUS

Region / Authority	Status
USA (FDA)	GRAS as flavoring agent (<10 ppm); OTC monograph (CFR 341)
European Union (EFSA)	Approved as flavoring (FL No: 03.001)
WHO	Listed in Essential Medicines List (as part of eucalyptus oil)
EU REACH	Registered; no SVHC classification
EU Cosmetics Regulation	Permitted; restricted in Japan (max. 0.3% in rinse-off products)

SECTION 10: SAFETY AND HEALTH INFORMATION

GHS Classification

Hazard Class	Category
Acute Toxicity (Oral)	Category 4 (H302)
Skin Irritation	Category 3 (H316)
Eye Irritation	Category 2A (H319)
Flammable Liquid	Category 3 (H226)
Signal Word	Warning

Hazard Statements (H-Codes)

Code	Statement
H226	Flammable liquid and vapor
H302	Harmful if swallowed
H316	Causes mild skin irritation
H319	Causes serious eye irritation

Toxicological Information

Parameter	Value
Oral LD50 (Rat)	2,480 mg/kg
Dermal LD50 (Rabbit)	> 5,000 mg/kg
Inhalation LC50 (Rat, 4h)	14 mg/L
Skin Irritation	Mild (non-irritant at ≤20%)
Eye Irritation	Moderate
Skin Sensitization	Low; rare cases in sensitive individuals
Genotoxicity	Negative (Ames test, micronucleus)
Reproductive Toxicity	No evidence at low doses

First Aid Measures

Exposure Route	Action
Inhalation	Move to fresh air. If breathing difficulty persists, seek medical attention.
Skin Contact	Wash with soap and water for 15 minutes.
Eye Contact	Rinse with water for 15 minutes. Seek medical attention if irritation persists.
Ingestion	DO NOT INDUCE VOMITING. Rinse mouth. If >10 mL swallowed, administer activated charcoal (under medical supervision).

SECTION 11: STORAGE AND SHELF LIFE

Parameter	Information
Storage Conditions	Cool (15-25°C), dry, well-ventilated area
Container Requirements	Tightly closed, light-resistant (amber glass or HDPE)
Protect From	Light, air (oxidation), heat, strong oxidizing agents, strong acids
Shelf Life	24 months (unopened original packaging)
Stability Note	Test for peroxide formation after 12 months

SECTION 12: TRANSPORT INFORMATION

Parameter	Information
UN Number	1993 (Flammable liquid, n.o.s.) or 1169 (Extracts, aromatic, liquid)
Hazard Class	3 (Flammable liquid)
Packing Group	III
Proper Shipping Name	Flammable liquid, n.o.s. (1,8-cineole)
Marine Pollutant	No

SECTION 13: PACKAGING OPTIONS

Packaging Type	Quantity	Material
Glass bottle	1-5 L	Amber glass
Plastic drum	200-250 kg	HDPE
Plastic pail	20-25 kg	HDPE
Aluminum foil bag	1-5 kg	Laminated aluminum

SECTION 14: COMPATIBLE MATERIALS

Material	Compatibility
Glass	Compatible
Stainless Steel (SS304/316)	Compatible
HDPE	Compatible
PTFE (Teflon)	Compatible
Viton	Compatible
Natural Rubber	Incompatible (swells)
Neoprene	Incompatible (swells)
EPDM	Incompatible (swells)
PVC	Incompatible (softens/swells)
LDPE	Incompatible (permeable)

SECTION 15: DRUG INTERACTIONS

Interaction	Description
CYP450 Inhibition	Inhibits CYP2B6 and CYP3A4 (mild). May increase levels of drugs metabolized by these enzymes (e.g., midazolam, ketamine, some antivirals).
Penetration Enhancement	Increases penetration of topical drugs (e.g., lidocaine, antifungals) through skin/mucosa.

SECTION 16: SUMMARY AND CRITICAL NOTES

Product Summary

Parameter	Value
Product	Eucalyptol (1,8-Cineole)
CAS Number	470-82-6
Appearance	Colorless to pale yellow liquid
Odor	Fresh, minty, camphoraceous
Boiling Point	176-177 °C
Primary Function	Mucolytic, anti-inflammatory, antimicrobial

Critical Notes

Mucolytic Activity: Eucalyptol increases ciliary beat frequency and airway hydration through TRPA1 activation.
Anti-inflammatory: Inhibits NF-κB pathway; reduces COX-2, PGE2, TNF-α, and IL-1β.
Natural Source: Primarily derived from eucalyptus oil (70-90% content).
GRAS Status: Approved as GRAS by FDA for flavoring (<10 ppm).
Safety: Low skin irritation; moderate toxicity at high oral doses (>2 g).
Children: Not suitable for children under 6 years of age.
Flammable: Flash point 49°C; store away from ignition sources.
Cooling Sensation: Activates TRPM8 receptors (weak; indirect effect).
Incompatibilities: Incompatible with natural rubber, neoprene, EPDM, PVC, LDPE.
Regulatory Status: Approved in EU (flavoring, FL No: 03.001), FDA (GRAS), and WHO Essential Medicines List.

IMPORTANT DECLARATION: This Technical Data Sheet (TDS) is for informational purposes only and has been prepared based on available technical data. The user is responsible for determining the product's suitability for their specific application and for complying with all local, national, and international regulations. For complete safety, storage, use, transport, waste, and regulatory compliance information, refer to the official Safety Data Sheet (SDS/MSDS) provided by the manufacturer/supplier. This document does not replace medical advice.

Eucalyptol, Cineol, Cineole, 470-82-6

EUCALYPTOL – OKALİPTOL

Images

Do you have questions? Let us help!