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]
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| 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)
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| 1902767 | |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.033.367 |
| EC Number |
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| 663435 | |
| KEGG | |
PubChem CID
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| UNII | |
| UN number | 2319 |
CompTox Dashboard (EPA)
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| 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: | |
  
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| 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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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
editTreatment 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
edit- ^ a b Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
- ^ a b M. Eggersdorfer (2005). "Terpenes". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a26_205. ISBN 978-3527306732.
- ^ a b Merck Index (12th ed.). 1996. p. 300. 1885.
- ^ Mediavilla, Vito, Simon Steinemann, Essential oil of Cannabis sativa L. strains. Journal of the International Hemp Association, 1997, 4(2):80-82.
- ^ "What is Delta 3 Carene?". ionizationlabs.com. Ionization Labs. Retrieved 6 August 2020.