3-Carene

3-Carene
Names
IUPAC names
3,7,7-Trimethylbicyclo[4.1.0]hept-3-ene
Car-3-ene
Other names
Δ3-Carene
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.033.367
KEGG
UNII
Properties
C10H16
Molar mass 136.24 g·mol−1
Density 0.86 g/cm3 (20 °C)[1]
Boiling point 170–172 °C (338–342 °F; 443–445 K)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

3-Carene is a bicyclic monoterpene consisting of fused cyclohexene and cyclopropane rings. It occurs as a constituent of turpentine,[2] with a content as high as 42% depending on the source. Carene has a sweet and pungent odor.[3], best described as fir needles, musky earth, and damp woodlands combination.[4]

A colorless liquid, it is not soluble in water, but miscible with fats and oils.[3] It is chiral, occurring naturally both as the racemate and enantio-enriched forms.

Reactions and uses

Treatment with peracetic acid gives 3,4-caranediol. Pyrolysis over ferric oxide induces rearrangement, giving p-cymene. Carene is used in the perfume industry and as a chemical intermediate.[2]

References

  1. 1 2 Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  2. 1 2 M. Eggersdorfer (2005). "Terpenes". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a26_205.
  3. 1 2 Merck Index (12th ed.). 1996. p. 300. 1885.
  4. ↑ Mediavilla, Vito, Simon Steinemann, Essential oil of Cannabis sativa L. strains. Journal of the International Hemp Association, 1997, 4(2):80-82.
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