Cineole
[CAS# 470-82-6]

Identification

• Classification: Chemical reagent >> Organic reagent >> Epoxide
• Name: Cineole
• Synonyms: 1,3,3-Trimethyl-2-oxabicyclo[2.2.2]octane; 1,8-Cineole; 1,8-Epoxy-p-menthane; 1,8-Oxido-p-menthane; Eucalyptol
• Molecular Formula: C₁₀H₁₈O
• Molecular Weight: 154.25
• CAS Registry Number: 470-82-6
• EC Number: 207-431-5
• FEMA: 2465
• SMILES: CC1(C2CCC(O1)(CC2)C)C

Properties

• Density: 0.9±0.1 g/cm³, Calc.^*, 0.928 g/mL (Expl.)
• Melting point: 1 °C (Expl.)
• Index of Refraction: 1.461, Calc.^*, 1.456 (Expl.)
• Boiling Point: 174.0±8.0 °C (760 mmHg), Calc.^*, 176 – 177 °C (Expl.)
• Flash Point: 50.9±15.3 °C, Calc.^*, 49 °C (Expl.)

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS02;GHS07 Warning
• Risk Statements: H226-H317
• Safety Statements: P210-P233-P240-P241-P242-P243-P261-P272-P280-P302+P352-P303+P361+P353-P321-P333+P317-P362+P364-P370+P378-P403+P235-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Flammable liquids	Flam. Liq.	3	H226
Skin sensitization	Skin Sens.	1B	H317
Skin sensitization	Skin Sens.	1	H317
Eye irritation	Eye Irrit.	2	H319
Flammable liquids	Flam. Liq.	2	H225
Acute toxicity	Acute Tox.	4	H302
Skin irritation	Skin Irrit.	2	H315
Serious eye damage	Eye Dam.	1	H318
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Respiratory sensitization	Resp. Sens.	1B	H334
Aspiration hazard	Asp. Tox.	1	H304
Specific target organ toxicity - repeated exposure	STOT RE	2	H373
Specific target organ toxicity - single exposure	STOT SE	3	H335
Specific target organ toxicity - single exposure	STOT SE	2	H371

• Transport Information: UN 1993

Discovery and Applications

Cineole, also known as eucalyptol, is a natural organic compound with a refreshing, minty aroma, predominantly found in eucalyptus oil. This monoterpene has been instrumental in traditional medicine and modern applications due to its distinctive properties and benefits.Cineole was first identified in the early 19th century by chemists extracting essential oils from the Eucalyptus globulus tree. Initially isolated through steam distillation, cineole emerged as the chief constituent of eucalyptus oil, constituting up to 90% of the oil's composition. The discovery marked the beginning of its extensive use in medicinal and industrial fields.

Cineole is renowned for its medicinal properties, particularly its role as a natural decongestant and expectorant. It helps alleviate symptoms of respiratory conditions such as asthma, bronchitis, and sinusitis by thinning mucus and facilitating easier breathing. Cineole's anti-inflammatory and antimicrobial characteristics also make it effective in treating respiratory infections and soothing irritated mucous membranes.

Cineole is a key ingredient in many over-the-counter cold remedies, including cough syrups, lozenges, and inhalants. Its pleasant aroma not only provides symptomatic relief but also enhances the patient’s comfort during illness.

In aromatherapy, cineole is celebrated for its invigorating scent and its ability to promote mental clarity and focus. Inhaling cineole can help reduce fatigue and boost mood, making it a popular choice for stress relief and cognitive enhancement. It is often used in diffusers and essential oil blends aimed at improving concentration and overall well-being.

Cineole's versatility extends to various industrial applications. It is utilized in the formulation of cleaning agents and air fresheners due to its potent disinfectant properties and refreshing fragrance. Its ability to act as a natural solvent and degreaser further enhances its value in these products, providing effective, eco-friendly cleaning solutions.

In the food industry, cineole is used as a flavoring agent to impart a minty, camphor-like taste to certain products. Its presence is notable in beverages, confectioneries, and culinary spices, where it adds a distinctive note to the overall flavor profile.

While cineole is generally safe for use in recommended quantities, excessive inhalation or ingestion can cause adverse effects such as nausea and vomiting. Therefore, it is essential to adhere to dosage guidelines in both medicinal and industrial applications.

References

Leita, B. A., Warden, A. C., Burke, N., O'Shea, M. S. and Trimm, D., 2010. Production of p-cymene and hydrogen from a bio-renewable feedstock-1,8-cineole (eucalyptus oil). Green Chemistry, 12, 70.
DOI: 10.1039/b916460j

Bhosle, D., Srinivasan, T., Elaiyabharathi, T., et al., 2025. A review on use of botanical extracts for the management of fall armyworm Spodoptera frugiperda (Smith, 1797) [Noctuidae, Lepidoptera]. J Plant Dis Prot, 132, 17.
DOI: 10.1007/s41348-024-01042-5

Obistioiu, D., Cristina, R. T., Schmerold, I., et al., 2014. Chemical characterization by GC-MS and in vitro activity against Candida albicans of volatile fractions prepared from Artemisia dracunculus, Artemisia abrotanum, Artemisia absinthium and Artemisia vulgaris. Chemistry Central Journal, 8, 6.
DOI: 10.1186/1752-153X-8-6