3-Carene

3-Carene is a bicyclic monoterpene found in the essential oils of various plants, including rosemary, pine and cannabis. It has a sweet and pungent odor, and is commonly used in fragrances and flavorings. Studies have shown that 3-Carene has anti-inflammatory and analgesic properties, making it potentially useful in the treatment of various medical conditions.

Reactions and Uses

• Treatment with peracetic acid gives 3,4-caranediol.
• Pyrolysis over ferric oxide induces rearrangement, giving -cymene.
• Carene is used in the perfume industry and as a chemical intermediate.
• Carene can be found in cannabis distillates naturally, affecting taste and smell.
• Present in mango, carene gives the fruit a pine-like flavor and aroma.

Characteristics

• Bicyclic monoterpene with fused cyclohexene and cyclopropane rings.
• Occurs in turpentine with content up to 42% depending on the source.
• Sweet and pungent odor resembling fir needles, musky earth, and damp woodlands.
• Colorless liquid insoluble in water but miscible with fats and oils.
• Chiral nature, occurring naturally as racemate and enantio-enriched forms.

Hazards

• GHS labeling: Danger.
• Hazard statements: H226, H304, H315, H317, H412.
• Precautionary statements include various safety measures.
• Boiling point at 170–172°C (338–342°F; 443–445K).
• Hazards related to exposure and handling are significant.

Chemical Properties

• Molecular weight: 100.033.367.
• Density: 0.86 g/cm at 20°C.
• Boiling point: 170–172°C.
• Not soluble in water but miscible with fats and oils.
• Occurs naturally in both racemate and enantio-enriched forms.

References

• Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health.
• M. Eggersdorfer (2005). Terpenes.
• Ullmanns Encyclopedia of Industrial Chemistry.
• Merck Index (12th ed.). 1996. p.300. 1885.
• Essential oil of Cannabis sativa L. strains. Journal of the International Hemp Association, 1997, 4(2):80-82.

3-Carene Data Sources