Chemistry:3-Carene

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3-Carene
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
EC Number
  • 236-719-3
663435
KEGG
UNII
UN number 2319
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 pictograms GHS02: FlammableGHS07: HarmfulGHS08: Health hazard
GHS Signal word Danger
H226, H304, H315, H317, H412
P210, P233, P240, P241, P242, P243, P261, P264, P272, P273, P280, P301+310, P302+352, P303+361+353, P321, P331, P332+313, P333+313, P362, P363, P370+378, P403+235, 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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Infobox references
Tracking categories (test):

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. 1.0 1.1 Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  2. 2.0 2.1 M. Eggersdorfer (2005). "Ullmann's Encyclopedia of Industrial Chemistry". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a26_205. 
  3. 3.0 3.1 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?". Ionization Labs. https://ionizationlabs.com/the-cannabis-terpene-carene/.