3-Carene

3-Carene
Names
	Preferred IUPAC name 3,7,7-Trimethylbicyclo[4.1.0]hept-3-ene
	Other names Δ3-Carene; Car-3-ene
Identifiers
CAS Number	13466-78-9 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	1902767
ChEBI	CHEBI:7;
ChEMBL	ChEMBL506854 ;
ChemSpider	10660720 ;
ECHA InfoCard	100.033.367
EC Number	236-719-3;
Gmelin Reference	663435
KEGG	C11382 ;
PubChem CID	26049;
UNII	H2M15SNR6N ;
UN number	2319
CompTox Dashboard (EPA)	DTXSID4047462 ;
	InChI InChI=1S/C10H16/c1-7-4-5-8-9(6-7)10(8,2)3/h6-8H,4-5H2,1-3H3 Key: KALFVDDBBPRATR-UHFFFAOYSA-N ; InChI=1/C10H16/c1-7-4-5-8-9(6-7)10(8,2)3/h6-8H,4-5H2,1-3H3 Key: KALFVDDBBPRATR-UHFFFAOYAY;
	SMILES CC1=CCC2C(C1)C2(C)C;
Properties
Chemical formula	C10H16
Molar mass	136.238 g·mol−1
Density	0.86 g/cm3 (20 °C)
Boiling point	170–172 °C (338–342 °F; 443–445 K)
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H226, H304, H315, H317, H412
Precautionary statements	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). verify (what is ?) 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 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

^ ^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.

[GESTIS-1] Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health

[UllmannEgg-2] M. Eggersdorfer (2005). "Terpenes". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a26_205. ISBN 978-3527306732.

[Merck-3] 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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