3-Carene

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3-Carene
Carene Carene, 3-.svg
Carene
Names
Preferred IUPAC name
3,7,7-Trimethylbicyclo[4.1.0]hept-3-ene
Other names
Δ3-Carene
Car-3-ene
Identifiers
3D model (JSmol)
1902767
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.033.367 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 236-719-3
663435
KEGG
PubChem CID
UNII
UN number 2319
  • InChI=1S/C10H16/c1-7-4-5-8-9(6-7)10(8,2)3/h6-8H,4-5H2,1-3H3 Yes check.svgY
    Key: KALFVDDBBPRATR-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C10H16/c1-7-4-5-8-9(6-7)10(8,2)3/h6-8H,4-5H2,1-3H3
    Key: KALFVDDBBPRATR-UHFFFAOYAY
  • CC1=CCC2C(C1)C2(C)C
Properties
C10H16
Molar mass 136.238 g·mol−1
Density 0.86 g/cm3 (20 °C) [1]
Boiling point 170–172 °C (338–342 °F; 443–445 K) [1]
Hazards
GHS labelling:
GHS-pictogram-flamme.svg GHS-pictogram-exclam.svg GHS-pictogram-silhouette.svg
Danger
H226, H304, H315, H317, H412
P210, P233, P240, P241, P242, P243, P261, P264, P272, P273, P280, P301+P310, P302+P352, P303+P361+P353, P321, P331, P332+P313, P333+P313, P362, P363, P370+P378, P403+P235, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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 a combination of fir needles, musky earth, and damp woodlands. [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]

Because carene can be found in cannabis naturally, it can also be found in cannabis distillates. Greater concentrations of carene in a distillate give it an earthier taste and smell. [5] 3-Carene is also present in mango, giving the fruit a characteristic pine-like flavor and aroma.

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. ISBN   978-3-527-30673-2.
  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.
  5. ↑ "What is Delta 3 Carene?". ionizationlabs.com. Ionization Labs. Retrieved 6 August 2020.
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